Naphthoquinones: 2011

Monday, September 19, 2011

2,3-Dichloro-1,4-naphthoquinone

STRUCTURE, SYNONYMS, BASIC INFORMATION and References
 

Does euphonious remind you of an attachment

    •   1,4-Naphthalenedione, 2,3-dichloro-
    • 1,4-Naphthoquinone, 2,3-dichloro-
    • 2, 3-Dichloro-.alpha.-naphthoquinone
    • 2, 3-Dichloronaphthoquinone
    • 2,3-Dichlor-1,4-naftochinon [Czech]
    • 2,3-Dichlor-1,4-naphthochinon
    • 2,3-Dichlor-1,4-naphthochinon [German]
    • 2,3-Dichloro-1, 4-naphthalenedione
    • 2,3-Dichloro-1,4-naphthalenedione
    • 2,3-Dichloro-1,4-naphthaquinone
    • 2,3-Dichloro-1,4-naphthoquinone
    • 2,3-Dichloronaphthoquinone
    • 2,3-Dichloronaphthoquinone-1,4
    • Algistat
    • CDS1_000275
    • CNQ
    • Compound 604
    • Dichlone
    • Dichlone [BSI:ISO]
    • Dichloronaphthoquinone
    • Diclone
    • ENT 3,776
    • Latka 604 [Czech]
    • Maybridge1_002563
    • Phygon
    • Phygon paste
    • Phygon seed protectant
    • Phygon XL
    • Quintar
    • Quintar 540F
    • Sanquinon
    • U.s. rubber 604
    • Uniroyal
    • US Rubber 604
    • USR 604

  1. Chemical Formula: C10H4Cl2O2
  2. Exact Mass: 225.95883
  3. Molecular Weight: 227.04356
  4. m/z: 225.96 (100.0%), 227.96 (64.3%), 226.96 (10.9%), 229.95 (10.2%), 228.96 (7.0%), 230.96 (1.1%)
  5. Elemental Analysis: C, 52.90; H, 1.78; Cl, 31.23; O, 14.09
  6. Solubility: Acetone, benzene, ether, xylene,
  7. Insoluble: water
  8. Appearance: Yellow needle crystal 
  9. Melting Point : 193oC;     Boiling Point:  275 oC
  10. Toxicity: Oral(Rat) : LD50＝1.3g/kg; Carp : LD50＝ 0.07ppm; Red killifish : LD50＝ 0.10ppm
  11. Redox Potential : 498mV
  12. Aplication: It is used as algicide and fungicide
  13. Uses : agricultural intermediate, catalyst and organic synthesis reagent
  14. IR (KBr): 475, 636, 707, 793, 821, 881, 1134, 1274, 1320, 1388, 1453, 1557, 1585, 1678 (>C=O), 1883, 1985, 2013, 2366 30440, 3097.
  15. 1HNMR( 300 MHz, CDCl3): 7.82 (dd, 2H, J=2.4 & 3.3, C5 &C8), 8.19 (dd, 2H, J=2.4 & 3.3, C6 &C7)
  16. Table 1: Antiproliferative activity against cervical cancer (HeLa) cells.
Conc.(µM)
Inhibition (%)
SD (±)
1
28
4.2
5
43
3.6
20
49
    4.8
  1.   Table 2: In vitro antifungal activity (MIC: μg/mL).
C. albicans
C. neoformans
S. schenckii
T. mentagraphytes
A. fumigatus
C. parapsilosis
0.78
3.12
0.78
1.56
1.56
1.56


18 References for the synthesis of 2,3-dichloro-1,4-naphthoquinone and analogs from 1960-2007
(Red reference are showing synthesis and reaction of 2,3-dichlonaphthoquinone and Blue reference are showing reaction of 2,3-dichlonaphthoquinone)
1)        2,3-Dichloro-1,4-naphthoquinone Sjostrand, Bengt Tore Lennart  U.S. 2955117, 04 Oct 1960
2)       Reactions of quinones with aromatic ethers.  V.  Triphenylene-1,4-quinones from 2,3-diaryl-1,4-benzoquinones.      Buchan, Robert; Musgrave, Oliver C.Journal of the Chemical Society, Perkin Transactions 1:  Organic and Bio-Organic Chemistry (1972-1999),  (6), 568-72; 1975
3)       Synthesis of some derivatives of 5-amino-1,4-naphthoquinone.      Slesarchuk, L. P.; Kolesnikov, V. T.; Boldyrev, B. G.Vestnik L'vovskogo Politekhnicheskogo Instituta, 96, 49-53; 1975
4)       Naphthoquinone coloring matters.  Part 2.  1,4-Naphthoquinones with electron-donating groups in the benzenoid ring.      Chu, Kwong-Yung; Griffiths, John.Journal of Chemical Research, Synopses, (5), 180-1; 1978
5)       A convenient synthesis of some highly functionalized chromones and indenones.      Roberge, Guy; Brassard, Paul. Synthetic Communications, 9(2), 129-39; 1979
6)       Reaction of -hydroxyanthraquinones with thionyl chloride.  Preparation of 1,10-anthraquinone derivatives.      Gorelik, M. V.; Titova, S. P.; Trdatyan, V. A.    Nauchno-Issled. Inst. Org. Poluprod. Krasitelei Zhurnal Organicheskoi Khimii, 15(1), 157-66; 1979
7)       Synthetic studies of naphthoquinone derivatives.  3.  Reactions of 5-substituted 2,3-dichloro- and 2,3,6,8-tetrachloro-1,4-naphthoquinones with anilines.      Kasai, Toshiyasu; Nakamori, Tateo; Sekiguchi, Kyoichi. Nippon Kagaku Kaishi,  (12), 1862-9; 1980
8)       Studies of the synthesis of naphthoquinone derivatives.  4.  Reactions of aniline with 2,3-dichloro-1,4-naphthoquinones having additional chloro substituents on the benzenoid ring.      Kasai, Toshiyasu; Nakamori, Tateo; Sawayama, Akio.Nippon Kagaku Kaishi,  (3), 416-23; 1981
9)       Synthesis of naphthoquinone derivatives.  V.  Synthesis of 2,3-disubstituted 5,8-diamino-1,4-naphthoquinones.      Kasai, Toshiyasu; Nakamori, Tateo; Furugaki, Koichi.Nippon Kagaku Kaishi,  (4), 536-43; 1981
10)   Synthesis, reactions and spectra of some fused polycyclic aromatic chlorocarbons, and related compounds.      Ballester, M.; Castaner, J.; Riera, J.; Pares, J. Anales de Quimica, Serie C:  Quimica Organica y Bioquimica, 76(2), 157-70; 1980
11)   A convenient synthesis of 2,3-dichloro-1,4-naphthoquinone-1-14C using a novel chlorination procedure.      Ehler, Kenneth W.; Pardini, Ronald S.Organic Preparations and Procedures International, 15(3), 157-60; 1983
12)   Naphthoquinone antipsoriatic agents.      Jones, Gordon H.; Young, John M. U.S., 4442127, 10 Apr 1984
13)   Study of 1,4-naphthoquinone.  VIII.  Nucleophilic substitution in a series of 2,3-dichloro-5-hydroxy-1,4-naphthoquinone and its derivatives.      Belitskaya, L. D.; Kolesnikov, V. T.Zhurnal Organicheskoi Khimii, 20(9), 1920-5; 1984
14)   Site-selective Diels-Alder reactions of 1,4,5,8-naphthodiquinones with anthracenes and successively with cyclopentadiene:  electronic effects vs. steric effects.      Hayakawa, Kenji; Aso, Mariko; Kanematsu, Ken. Journal of Organic Chemistry, 50(12), 2036-40; 1985
15)   Acyloxynaphthalene antipsoriatic agents.      Jones, Gordon H.; Venuti, Michael C.; Young, John M. Eur. Pat. Appl., 146145, 26 Jun 1985
16)   Sulfonation and sulfochlorination of 2,3-dichloro-1,4-naphthoquinones.      Shishkina, R. P.; Mamatyuk, V. I.; Fokin, E. P. Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,  (4), 855-7; 1985
17)   Dimeric naphthoquinones.  XVI.  Synthesis of maritinone and other 8,8'-bijuglones.      Laatsch, Hartmut. Liebigs Annalen der Chemie,  (12), 2420-42; 1985
18)   2,3-Dichloro-1,4-naphthoquinone.      Suzuki, Hisashi; Yabe, Hirota.  Jpn. Kokai Tokkyo Koho, 61018742, 27 Jan 1986, Showa
19)   Topical nonsteroidal antipsoriatic agents.  1.  1,2,3,4-Tetraoxygenated naphthalene derivatives.      Jones, Gordon H.; Venuti, Michael C.; Young, John M.; Murthy, D. V. Krishna; Loe, Brad E.; Simpson, Richard A.; Berks, Andrew H.; Spires, Doreen A.; Maloney, Patrick J.; et al. Journal of Medicinal Chemistry, 29(8), 1504-11; 1986
20)   1,4-Anthraquinonoid dienophiles applicable to synthesis of linear tetracycles.      Cameron, Donald W.; Conn, Costa; Crossley, Maxwell J.; Feutrill, Geoffrey I.; Fisher, Mark W.; Griffiths, Peter G.; Merrett, Bryan K.; Pavlatos, Dennis.Tetrahedron Letters, 27(21), 2417-20; 1986
21)   Synthetic studies of the rubradirins.  A strategy for the incorporation of the ansa bridge.      Kozikowski, Alan P.; Xia, Yan.    Journal of Organic Chemistry, 52(7), 1375-8; 1987
22)   Naphthalene antipsoriatic and antiinflammatory agents and lipoxygenase inhibitors and a process for making them.      Krishna Murthy, Dodballapur Venkataramiah; Young, John M.; Venuti, Michael C.  Eur. Pat. Appl., 215622, 25 Mar 1987
23)   Preparation of 5-hydroxynaphtho[2,3-d]thiazole-4,9-dione as medical bactericide.      Nishino, Isao; Kimura, Harutaka.  Jpn. Kokai Tokkyo Koho, 62234076, 14 Oct 1987, Showa
24)   Preparation of 5-hydroxynaphtho[2,3-d]thiazole-4,9-dione as a veterinary bactericide.      Nishino, Isao; Kimura, Harutaka; Araki, Seiichi. Jpn. Kokai Tokkyo Koho, 62234019, 14 Oct 1987, Showa
25)   Synthesis and cytotoxic activity of aziridinyl-1,4-naphthoquinones and -naphthazarins.      Horowska, Barbar; Mazerska, Zofia; Ledochowski, Andrzej; Cristalli, Gloria; Franchetti, Palmarisa; Martelli, Sante. European Journal of Medicinal Chemistry, 23(1), 91-6; 1988
26)   Synthetic studies on nogalamycin congeners.  II.  Chiral synthesis of the CDEF-ring system of nogalamycin.      Kawasaki, Motoji; Matsuda, Fuyuhiko; Terashima, Shiro. Tetrahedron, 44(18), 5713-25; 1988
27)   Fries rearrangement and Dakin reaction in the benzo-2,1,3-thiadiazole series.      Belen'kaya, I. A.; Krokhina, G. P.; Sirik, S. A.; Andronati, S. A. Khimiya Geterotsiklicheskikh Soedinenii,  (12), 1683-7; 1987
28)   Naphthazarin derivatives as antitumor agents.      Masuda, Kazuaki.  Jpn. Kokai Tokkyo Koho, 62289543, 16 Dec 1987, Showa
29)   Electronic structure and near-infrared spectra of diquinone anion radicals.      Almlof, Jan E.; Feyereisen, Martin W.; Jozefiak, Thomas H.; Miller, Larry L.Journal of the American Chemical Society, 112(3), 1206-14; 1990
30)   Dichloroquinones as dienophiles:  synthesis of alizarin derivatives.      Cameron, Donald W.; Feutrill, Geoffrey I.; Keep, Philip L. C.    Tetrahedron Letters, 30(38), 5173-6; 1989
31)   Chlorination of 1,4-naphthoquinones.      Kitahara, Tadao; Kitahara, Satoru; Minemura, Muneharu; Akyama, Ukichi.Jpn. Kokai Tokkyo Koho, 03246250, 01 Nov 1991, Heisei
32)   The Pursuit of Perchlorotriphenylene.      Shibata, Kazusato; Kulkarni, Abhijit A.; Ho, Douglas M.; Pascal, Robert A., Jr. Journal of Organic Chemistry, 60(2), 428-34; 1995
33)   Use of Thiazyl Chlorides, Alkyl Carbamates, and Thionyl Chloride To Fuse 1,2,5-Thiadiazoles to Quinones and To Oxidize, Chlorinate, and Aminate Them.      Shi, Shuhao; Katz, Thomas J.; Yang, Bingwei V.; Liu, Longbin. Journal of Organic Chemistry, 60(5), 1285-97; 1995
34)   Synthesis and Characterization of Novel Donor-Acceptor Naphthoquinone Derivatives with Photoinduced Charge-Transfer Properties. A Joint Experimental and Theoretical Study.      Illescas, Beatriz; Martin, Nazario; Segura, Jose L.; Seoane, C.; Orti, Enrique; Viruela, Pedro M.; Viruela, Rafael.    Journal of Organic Chemistry, 60(17), 5643-50; 1995
35)   Chemistry of naphthazarin derivatives. Reaction of unsubstituted and substituted 2,5,8-trihydroxy-1,4-naphthoquinones and derivatives of 2,5,8-trihydroxy-1,4-naphthoquinone 1-imines with citral.      Chizhova, A. Ya.; Anufriev, V. F.; Novikov, V. L. Zhurnal Organicheskoi Khimii, 31(2), 237-43; 1995
36)   Synthesis of acetyl- and methoxycarbonylnaphthazarins.      Farina, F.; Valderrama, J. A.; Gonzalez, L. Anales de Quimica, 91(5-6), 440-448; 1995
37)    A Benzylation Study of 2,3-Dichloronaphthazarin. Cheng, C. C.;  Chang, He Xi;  Morton, Martha; Velde,  David Vander  Synthetic Communications, 26(10), 1985-93; 1996
38)   The synthesis of a symmetrically substituted-a -octa(isopentoxy)anthralocyanine  Bedworth, Peter V.; Perry Joseph W. ; Marder, Seth R. Chemical Communications (Cambridge),  (15), 1353-1354; 1997
39)     Synthesis of Hallachrome. Cameron, Donald W.; Coller, D. Ross; McDonald,   Clinton A.  Australian Journal of Chemistry, 52(9), 833-836; 1999
40)   Synthesis of organic third-order nonlinear optical materials of dioxonaphthothiazole and dibenzothianthrene compounds.     Gao, Jian-rong; Shen, Wei-guang; Cheng, Lu-bai; Chen, Xing. Zhejiang Gongye Daxue Xuebao, 28(1), 14-17; 2000
41)   Regiocontrolled synthesis of the trimeric quinone framework of conocurvone.      Emadi, Ashkan; Harwood, John S.; Kohanim, Sahar; Stagliano, Kenneth W. Organic Letters, 4(4), 521-524; 2002
42)   Sonochemical chloro-oxidation of phenols using HCl-H2O2.      Bhatkhande, B. S.; Adhikari, M. V.; Samant, S. D.    Ultrasonics Sonochemistry, 9(1), 31-35; 2002
43)   Naturalization and modification of natural colors of flowers. I. Naphthofuroquinolinedione dyes.      Boscornea, Cristian; Pasolea, Florin; Tarabasanu Mihaila, Corneliu; Boscornea, Corina. Revista de Chimie (Bucharest, Romania), 53(5), 394-403; 2002
44)   Pigments of fungi. Part 70. Total synthesis of (R)-semixanthomegnin and the x-ray crystal structure of ( )-7-chloro-10-methoxy-3-methyl-3,4-dihydro-1H-naphtho[2,3-c]pyran-1,6,9-trione. Australian Journal of Chemistry, 56(1), 49-57; 2003
45)   Chemistry of naphthazarin derivatives. 9. Direct observation of prototropic tautomerism of (poly)hydroxynaphthazarins by IR spectroscopy.      Glazunov, V. P.; Yakubovskaya, A. Ya.; Pokhilo, N. D.; Bochinskaya, N. V.; Anufriev, V. Ph. Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya), 52(1), 198-207; 2003
46)    Process for preparation of naphthoquinonothiazole derivatives as organic third-order non-linear optical materials.      Gao, Jianrong; Sheng, Weijian; Xiang, Bin; Shan, Weiguang; Cheng, Lubai. Faming Zhuanli Shenqing Gongkai Shuomingshu, 1440966, 10 Sep 2003
47)   PCT Int. Appl., 2005095376, 13 Oct 2005
48)   Preparation of naphthoquinone derivatives as PI3 kinase inhibitors for treatment of cancer.      Chang, Junbiao; Xie, Weilin; Wang, Lei. Faming Zhuanli Shenqing Gongkai Shuomingshu, 1587255, 02 Mar 2005
49)   Synthesis of 1,4,5,8-tetramethoxynaphthalene-2-carboxaldehyde.      Xu, Defeng; Guan, Pengjian; Mao, Zhiqiang; Wang, Zhenmo; Li, Shaoshun  Zhongguo Yiyao Gongye Zazhi, 35(10), 583-585; 2004
50)   Synthesis and antifungal activity of naphthalene-1,4-diones modified at positions 2, 3, and 5.      Ryu, Chung-Kyu; Chae, Mi Jin. Archives of Pharmacal Research, 28(7), 750-755; 2005
51)   New cytotoxic furoquinones obtained from terpenyl-1,4-naphthoquinones and 1,4-anthracenediones.      Miguel del Corral, Jose M.; Castro, M. Angeles; Oliveira, Alaide B.; Gualberto, Simone A.; Cuevas, Carmen; San Feliciano, Arturo.    Bioorganic & Medicinal Chemistry, 14(21), 7231-7240; 2006
52)   Study on synthesis of 2,3-dichloro-1,4-naphthoquinone.      Cao, Xiao-qun; Liu, Xin; Cheng, Yue-shan.   Jingxi Yu Zhuanyong Huaxuepin, 14(3/4), 16-17; 2006
53)   Quinone antitumor compounds, particularly 1,4-anthraquinones and their derivatives, process for their preparation, and their uses.      Molina Orden, Maria Teresa; Honghao, Sun; Taliansky Chamudis, Sandra; Carnero Moya, Amancio; Blanco Rodriguez, Fernando; Moneo Ocana, Maria Victoria. PCT Int. Appl., 2007026041, 08 Mar 2007
54)   Chinese Chemical Letters, 17(7), 871-873; 2006
55)   Hecheng Huaxue, 15(1), 16-19; 2007
                                                          
References for the reaction of 2,3-dichloro-1,4-naphthoquinone and analogs (1954-2007):
  1. Preparation of some imidazole derivatives of 1,4-naphthoquinone.      Hoover, John R. E.; Day, Allan R. Journal of the American Chemical Society, 76, 4148-52; 1954
  2. Synthesis of substituted amino, aminovinyl, and aminobutadienyl-p-quinones.      Buckley, D.; Henbest, H. B.; Slade, P. Journal of the Chemical Society, 4891-900; 1957
  3. Reactions between quinones and unsaturated amines. II. Detection of N-alkylvinylamines in equilibrium with ethylideneamines.      Honbest, H. B.; Slade, P. Journal of the Chemical Society, 1555-7; 1960
  4. Amine oxidation. V. Dehydrogenation of diethylamine in the presence of 2,3-dichloronaphthoquinone.      Henbest, H. B.; Slade, P. Journal of the Chemical Society, 1558-60; 1960
  5. 2,3-Dichloro-1,4-naphthoquinone.      Sjostrand, Bengt Tore Lennart.  U.S. 2955117, 04 Oct 1960
  6. Reactions of -dicarbonyl compounds and quinones with diazoalkanes. V. Reactions of substituted p-benzo- and -naphthoquinones with diazomethane.      Eistert, Bernd; Fink, Herbert; Mueller, Anneliese. Chemische Berichte, 95, 2403-15; 1962
  7. Heterocyclic quinones from 2,3-dichloro-1,4-naphthoquinone. Sartori, M. F.    Chem. Rev., 63, 279-96; 1963
  8. Reaction of 2,3-dichloronaphthoquinone with nucleophiles. II. Reaction with ethyl acetoacetate.      Reynolds, G. A.; VanAllan, J. A.; Adel, R. E.  Journal of Organic Chemistry, 30(11), 3819-24; 1965
  9. 2,3,5,6-Tetraamino-1,4-benzoquinone.  Preparation, properties, and reactions.      Winkelmann, Erhardt.    Farbwerke Hoechst A.-G.,  Frankfurt/M., Tetrahedron, 25(12), 2427-54; 1969
  10. 4,9-Methano[11]annulenone.  Ten- -electron analog of tropone.      Vogel, Emanuel; Grimme, Walter; Reisdorff, J.; Juenemann, W.    Journal of the American Chemical Society, 92(21), 6335-7; 1970
  11. Experiments to study meson resonances.      Clark, Alan R.; Conforto, G.; Kenney, V. P.; Key, A. W.; Neal, H. A.; Pine, J. U. S. At. Energy Comm.,  (TID-25473(Vol. 4)), 237-66; 1969
  12. Reactions of quinones with aromatic ethers.  V.  Triphenylene-1,4-quinones from 2,3-diaryl-1,4-benzoquinones.      Buchan, Robert; Musgrave, Oliver C. Journal of the Chemical Society, Perkin Transactions 1:  Organic and Bio-Organic Chemistry (1972-1999),  (6), 568-72; 1975
  13. Cyclization reactions of quinonylmethane dyes and analogous merocyanines.  3.  Quinoid derivatives of anellated tetrahydroisoquinolinoquinoxaline.  Cyclization following the 1,7-shift of hydrogen.      Schelz, Dieter; Priester, Martin. Helvetica Chimica Acta, 58(8), 2536-45; 1975
  14. Studies on benzimidazole derivatives.  XL.  Reaction of mercapto derivatives of azoles with haloquinones.      Simonov, A. M.; Komissarov, V. N.    Khimiya Geterotsiklicheskikh Soedinenii,  (6), 783-5; 1976
  15. Synthesis of some derivatives of 5-amino-1,4-naphthoquinone.      Slesarchuk, L. P.; Kolesnikov, V. T.; Boldyrev, B. G. Vestnik L'vovskogo Politekhnicheskogo Instituta, 96, 49-53; 1975
  16. Synthesis and properties of charge transfer complexes and autocomplexes.  XVIII.  Some water-soluble derivatives of 1,4-naphthoquinone.      Dregeris, J.; Liepina, I.; Freimanis, J.  Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija,  (4), 460-4; 1977
  17. Reactions of ketene acetals.  IX. The synthesis of naphthoquinones from benzoquinones.      Grandmaison, Jean Louis; Brassard, Paul.    Tetrahedron, 33(16), 2047-53; 1977
  18. A convenient synthesis of naphthazarin and naphthopurpurin.      Lewis, John R.; Paul, John.    Anorganische Chemie, Organische Chemie  (1977),  32B(12),  1473-5. 
  19. Naphthoquinone coloring matters.  Part 2.  1,4-Naphthoquinones with electron-donating groups in the benzenoid ring.      Chu, Kwong-Yung; Griffiths, John. Journal of Chemical Research, Synopses,  (5), 180-1; 1978
  20. Synthesis and IR spectra of some new benzo[a] phenazine derivatives.      Agarwal, N. L.; Mital, R. L. Philippine Journal of Science, 105(3), 125-32; 1978
  21. A convenient synthesis of some highly functionalized chromones and indenones.      Roberge, Guy; Brassard, Paul. Synthetic Communications, 9(2), 129-39; 1979
  22. Reaction of -hydroxyanthraquinones with thionyl chloride.  Preparation of 1,10-anthraquinone derivatives.      Gorelik, M. V.; Titova, S. P.; Trdatyan, V. A.    Zhurnal Organicheskoi Khimii, 15(1), 157-66; 1979
  23. A convenient method for the synthesis of naphtho[2,3-b]furan-4,9-diones.      Kuo, Hsien-Saw; Hotta, Kazuo; Yogo, Motoi; Yoshina, Shigetaka. Synthesis,  (3), 188-9; 1979
  24. Naphthoquinone coloring matters.  Part 4.  Amino-substituted 1,2-dimethylnaphth[2,3-d]imidazole-4,9-diones.      Green-Buckley, Graham; Griffiths, John. Journal of the Chemical Society, Perkin Transactions 1:  Organic and Bio-Organic Chemistry (1972-1999),  (3), 702-7; 1979
  25. Naphthoquinone coloring matters.  Part 3.  Synthesis and electronic absorption spectra of 1,4-naphthoquinones containing electron donor groups in both rings.      Chu, Kwong Yung; Griffiths, John. Journal of the Chemical Society, Perkin Transactions 1:  Organic and Bio-Organic Chemistry (1972-1999),  (3), 696-701; 1979
  26. Heterocyclic quinonoid chromophoric systems:  Part II.  Reaction of 2,3-dichloro-1,4-naphthoquinone with 3-cyano-4-methyl-6-hydroxy-2(1H)-pyridone and its N-substituted derivatives.      Ayyangar, N. R.; Kolhe, P. Y.; Tilak, B. D. Indian Journal of Chemistry, Section B:  Organic Chemistry Including Medicinal Chemistry, 17B(2), 100-3; 1979
  27. Angular heterocycles:  synthesis of some substituted p-bromoanilino-12H-benzo[a]phenothiazines.      Tiwari, J. P.; Mital, R. L.  Indian Journal of Chemistry, Section B:  Organic Chemistry Including Medicinal Chemistry, 17B(4), 408-9; 1979
  28. Synthesis and properties of charge transfer complexes and autocomplexes.  XXIV.  Synthesis of molecular autocomplexes of a series of 1,4-naphthoquinone containing long hydrocarbon chains.      Dregeris, J.; Novicka, D.; Freimanis, J. Latvijas PSR Zinatnu Akademijas Vestis, Kimijas Serija,  (6), 692-7; 1979
  29. Studies on the syntheses of condensed indole-4,7-dione derivatives.  I.  Syntheses of benz[f]indole-4,9-diones starting from 2,3-dichloronaphthoquinone.      Okamoto, Masao; Ohta, Shunsaku; Terada, Shinichiro. Yakugaku Zasshi, 99(12), 1219-24; 1979
  30. Synthesis of 2-chloro-3-anilino-5-hydroxy-1,4-naphthoquinone.      Kolesnikov, V. T. Visnik L'viv. Politekhn. In-tu,  (131), 70-2; 1979
  31. Some chloroacetylamino derivatives of 5-nitro- and 5-amino-1,4-naphthoquinones.      Slesarchuk, L. P.; Kolesnikov, V. T.  Visnik L'viv. Politekhn. In-Tu  (1979),   (131),  66-9
  32. Heterocyclic quinonoid chromophoric systems.  Part VI.  Reaction of 2,3-dichloro-1,4-naphthoquinone with homophthalimides and other compounds containing a reactive methylene group.      Ayyangar, N. R.; Kolhe, P. Y.; Tilak, B. D. Indian Journal of Chemistry, Section B:  Organic Chemistry Including Medicinal Chemistry, 19B(10), 836-43; 1980
  33. Synthetic studies of naphthoquinone derivatives.  3.  Reactions of 5-substituted 2,3-dichloro- and 2,3,6,8-tetrachloro-1,4-naphthoquinones with anilines. Kasai, Toshiyasu; Nakamori, Tateo; Sekiguchi, Kyoichi.    Nippon Kagaku Kaishi,  (12), 1862-9; 1980
  34. Reaction of 2,3-dichloro-5-hydroxy-1,4-naphthoquinone with sodium methylate.      Kolesnikov, V. T.; Belitskaya, L. D.; Rozhilo, L. G. Vestnik L'vovskogo Politekhnicheskogo Instituta, 139, 112-14; 1980
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  146.  Synthesis of Some Novel Naphthoquinone Fused Selenazoles and 2-Amino-3-alkylseleno-1,4-naphthoquinones. Ruan, Ming-De; Wu, Zheng-Jie; Fan, Wei-Qiang; Zhou, Xun-Jun; Ma, Rong-Shen Heterocycles, 37(1), 323-9; 1994
  147. Jpn. Kokai Tokkyo Koho, 06065249, 08 Mar 1994, Heisei
  148. Youji Huaxue, 13(6), 612-15; 1993
  149.  The Influence of the Axial Chirality of Dibenzo[a,c]cyclooctene on the Configuration of Its Photo-Diels-Alder Adducts. Burger, Ulrich; Lottaz, Pierre-André; Millasson, Patricia; Bernardinelli,  Gérard  Helvetica Chimica Acta, 77(3), 850-8; 1994
  150. Journal of the Chemical Society, Perkin Transactions 1:  Organic and Bio-Organic Chemistry (1972-1999),  (15), 2191-5; 1994
  151. Liebigs Annalen der Chemie,  (10), 1081-9; 1993
  152. Collection of Czechoslovak Chemical Communications, 58(5), 1191-4; 1993
  153.  Chemical Interactions between 1,2,4-Triazole-3-thiols and π-Acceptors  Hassan, Alaa A.;  Mohamed, Nasr K.  Ibrahim; Yusria R.;  Sadek, Kamal U.;  Mourad, Aboul-Fetouh E.  Bulletin of the Chemical Society of Japan, 66(9), 2612-16; 1993
  154.  First example of selenium transfer reaction of primary selenoamides and selenourea. Novel synthesis of dialkyl diselenides from alkyl halides Ming-De, Ruan; Hua-Rong, Zhao; Wei-Qiang, Fan; Xun-Jun, Zhou Journal of Organometallic Chemistry, 485(1-2), 19-24; 1995
  155.  A Novel Synthesis of Some Naphtho[2,3-d]Thiazole-4,9-Diones From Lawsone Brahmeshwari;  G.; Rao, V. Rajeswar;  Kumari, T. Surya; Rao, T. V. Padmanabha  Phosphorus, Sulfur and Silicon and the Related Elements, 92(1-4), 51-6; 1994
  156.  Reaction of N1, N2-diarylamidines with chloranil and 2,3-dichloro-1,4-naphthoquinone Döpp, Dietrich; Gomaa, Mohsen Abdel-Motaal; Henkel, Gerald; El-Din; Ahmed Mokhtar Nour Journal of Heterocyclic Chemistry, 32(2), 603-10; 1995
  157.  Use of Thiazyl Chlorides, Alkyl Carbamates, and Thionyl Chloride To Fuse 1,2,5-Thiadiazoles to Quinones and To Oxidize, Chlorinate, and Aminate Them Shi, Shuhao; Katz, Thomas J.;  Yang, Bingwei V.;  Liu Longbin Journal of Organic Chemistry, 60(5), 1285-97; 1995
  158. Monatshefte fuer Chemie, 126(6/7), 653-62; 1995
  159.   The unexpected reactivity of 1,3-dithiol-2-ylphosphonate esters with 2,3-dichloro-p-benzoquinones: Synthesis and redox properties of novel donor-acceptor systems Martín, Nazario; Sánchez, Luis; Seoane, Carlos; Garín, Javier; Orduna, Jesús Tetrahedron Letters, 36(39), 7153-6; 1995
  160.  Design of antineoplastic agents on the basis of the ldquo2-phenyl-naphthalene-typerdquo structural pattern. 3. synthesis and biological activity evaluation of 5H-benzo[b]naphtho-[2,3-d]pyrrole-6,11-dione derivatives (p 113-117)
    Yi-Lin Luo, Ting-Chao Chou, C. C. Cheng     Journal of Heterocyclic Chemistry, 33(1), 113-17; 1996
  161.  Synthesis and Characterization of Novel Donor-Acceptor Naphthoquinone Derivatives with Photoinduced Charge-Transfer Properties. A Joint Experimental and Theoretical Study Beatriz Illescas, Nazario Martin, Jose L. Segura, C. Seoane, Enrique Orti, Pedro M. Viruela, Rafael Viruela Journal of Organic Chemistry, 60(17), 5643-50; 1995.
  162. Revue Roumaine de Chimie, 40(2), 165-72; 1995
  163.   Reaction of Imines with Naphthoquinones and 2-(Dicyanomethylene)-1,3-indandione  Gomaa, Mohsen Abdel-Motaal Bulletin of the Chemical Society of Japan, 68(11), 3131-5; 1995
  164. Izvestiya Akademii Nauk, Seriya Khimicheskaya,  (12), 2451-4; 1995
  165. Pharmazie, 52(1), 23-28; 1997
  166. Pharmazie, 52(4), 282-287; 1997
  167. Pharmazie, 52(8), 589-593; 1997
  168. Synthesis of 2-Amino-1,2,3-triazole Derivatives from Vicinal Diazides Sun, Duoli; Watson, William H.  Journal of Organic Chemistry, 62(12), 4082-4084; 1997.
  169. Pharmazie, 52(4), 282-287; 1997
  170. Zhurnal Organicheskoi Khimii, 32(10), 1537-1539; 1996
  171. Zhurnal Organicheskoi Khimii, 32(9), 1429-1431; 1996
  172.  Novel Synthesis of Oxadiaza Heterocycles and Thiadiazocine Derivatives Mohamed,  Nasr K.;  J. Chem. Res. (S), 1997, 144 Journal of Chemical Research, Synopses,  (4), 144-145; 1997
  173.  2-chloro-3-arylamino-1,4-naphthoquinone derivatives, process for preparation Moon, Chang-Kiu; Ryu, Chung-Kyu, U.S., 5654321, 05 Aug 1997
  174. Khimiko-Farmatsevticheskii Zhurnal, 31(6), 17-18; 1997
  175. Croatica Chemica Acta, 70(4), 1039-1045; 1997
  176. Monatshefte fuer Chemie, 129(2), 205-212; 1998
  177. Afinidad, 57(485), 67-71; 2000
  178.  2-Chloro-3-(4-morpholino)-1,4-naphthoquinone,  Bhattacharyya, ukanta  Molecules [Electronic Publication], 5(4), M160; 2000
  179.   Synthesis of N-Quinonyl Carbamates via 2-Chloro-3-isocyanato-1,4-naphthoquinone Bittner, Shmuel; Temtsin, Galina; Sasson, Yoel  Synthesis,  (8), 1084-1086; 2000
  180.  Synthesis and antibacterial activity of some novel thiourea, naphtho[2,3-d]thiazole, quinazoline and thieno[2,3-d]pyrimidine derivatives containing sulfonamido moieties.  El-Gaby,  M. S. A. Phosphorus, Sulfur and Silicon and the Related Elements, 156, 157-171; 2000
  181.  Quinonic Enaminones; Synthesis of New Dialkylaminovinyl and Bis(dialkylaminovinyl) Derivatives of Quinones  Alnabari, Mohammad; Bittner, Shmuel Synthesis,  (8), 1087-1090; 2000
  182. Synthesis of some new fluorinated phenothiazines.      Taneja, Vineeta Khatri nee; Garg, Urmila Gupta nee; Gorver, Vineeta Sareen nee; Sharma, Kanti.    Asian Journal of Chemistry  (2000),  12(4),  1273-1276
  183.  Synthesis and radiation stability of novel biologically active sulfur compounds derived from 1,2-bis(4-amino-5-mercapto-s-triazol-3-yl)ethane. Ghorab, M. M.; El-Sharief, A. M. Sh.; Ammar, Y. A.; Mohamed, Sh. I Farmaco, 55(5), 354-361; 2000
  184. Heterocyclic dyes, their production and their use.  Kaul, Bansi Lal; Piastra, Bruno; Wolf, Valerie. Eur. Pat. Appl., 1061103, 20 Dec 2000
  185.  Studies on the synthesis of some pyrazolo[1,5-a]pyrimidines bearing sulfonamido moieties.      El-Gaby, Mohamed S. A.; Sayed, Ahmed Z.; Abu-Shanab, Fathi A.; Hussein, Abdel M.   Phosphorus, Sulfur and Silicon and the Related Elements, 164, 1-10; 2000
  186.  Synthesis of some new fused and polyfused quinoxalines.      Abdel-Ghany, H. Phosphorus, Sulfur and Silicon and the Related Elements, 164, 259-268; 2000
  187. Chemistry of L-ascorbic acid. Part 3. Photoreduction of quinones with 5,6-O-isopropylidene-L-ascorbic acid.      Kulkarni, Mukund G.; Kate, Sandesh D.    Perkin 1,  (24), 4242-4244; 2000
  188. Synthesis of new sulfonamide drugs. Mohamed, Shaaban Kamel.    Afinidad, 57(490), 451-456; 2000
  189. Some reactions with tetrahydropyrimidine-2-thione: synthesis of thiazolopyrimidine, pyranothiazolopyrimidine, and pyrimidothiazoloquinoxaline derivatives as anticancer agents.      Ismail, M. M. F. Al-Azhar Journal of Pharmaceutical Sciences, 23, 1-10; 1999
  190. Heterocyclic dyes with condensed rings derived from 1,3-dihydro-2H-benzimidazole-2-thiones. Benzimidazo[2,1-b]naphtho[2,3-d]thiazole-7,12-diones.      Raditoiu, Valentin; Wagner, Luminita; Raditoiu, Alina; Ardeleanu, Petrea; Grigoriu, Nicoleta; Tarabasanu-Mihaila, Corneliu. Revista de Chimie (Bucharest, Romania), 52(4), 199-205; 2001
  191. Journal of Chemistry, 12(4), 1273-1276; 2000
  192. Amino acids in the synthesis of heterocyclic systems: The synthesis of triazinoquinazolinones, triazepinoquinazolinones and triazocinoquinazolinones of potential biological interest.      El-Sharief, A. M. Sh.; Ammar, Y. A.; Zahran, M. A.; Ali, A. H.; El-Gaby, M. S. A.    Molecules [online computer file], 6(3), 267-278; 2001
  193.  N,N-bis(quinonyl)amines; synthesis and X-ray structure.  Bittner, S.; Meenakshi, C.; Temtsin, G.  Tetrahedron, 57(34), 7423-7429; 2001
  194.  Rhodium generated carbonyl ylides with p-quinones: synthesis of oxa-bridged polycyclic systems.      Muthusamy, S.; Babu, S. A.; Gunanathan, C.; Suresh, E.; Dastidar, P.; Jasra, R. V. Tetrahedron, 57(32), 7009-7019; 2001
  195. Synthesis of 3-(benzotriazol-1-yl)naphthoquinone derivatives.      Ganushchak, N. I.; Romanyuk, A. L.; Litvin, B. L.; Lys, R. I.; Polishchuk, O. P. Russian Journal of General Chemistry (Translation of Zhurnal Obshchei Khimii), 71(2), 286-289; 2001
  196. New quinone-amino acid conjugates linked via a vinylic spacer.  Alnabari, Mohammad; Bittner, Shmuel. Amino Acids, 20(4), 381-387; 2001
  197. Synthesis of organic third-order nonlinear optical materials of dioxonaphthothiazole and dibenzothianthrene compounds. Gao, Jian-rong; Shen, Wei-guang; Cheng, Lu-bai; Chen, Xing.   Zhejiang Gongye Daxue Xuebao, 28(1), 14-17; 2000
  198. Palladium-catalyzed cross coupling of arylboronic acids with 2-chloro-1,4-naphthoquinones: the synthesis of 2-aryl- and 2,3-diaryl-1,4-naphthoquinones.  Best, Wayne M.; Sims, Colette G.; Winslade, Merilyn. Australian Journal of Chemistry, 54(6), 401-404; 2001
  199. Synthesis, electrochemical and spectral properties of some -N-quinonyl amino acids.      Bittner, S.; Gorohovsky, S.; Paz-Tal, O.; Becker, J. Y.    Amino Acids, 22(1), 71-93; 2002
  200. Novel heterocycles from creatinine.      Mourad, Aboul-Fetouh E.; Hassan, Alaa A.; Mohamed, Nasr K.; Aly, Ashraf A.; Ali, Bahaa A.    Heterocyclic Communications, 7(6), 541-548; 2001
  201.  Synthesis and electrochemical studies on a crown ether bearing a naphthoquinone acceptor.      Bond, Alan M.; Ghiggino, Kenneth P.; Hogan, Conor F.; Hutchison, James A.; Langford, Steven J.; Lygris, Emmanuel; Paddon-Row, Michael N. Australian Journal of Chemistry, 54(12), 735-738; 2001
  202. Construction of fused cyclooctanoid ring systems via seven-membered ring carbonyl ylides.      Muthusamy, Sengodagounder; Babu, Srinivasarao Arulananda; Gunanathan, Chidambaram; Suresh, Eringathodi; Dastidar, Parthasarathi. Ammar, Y. A.; Ghorab, M. M.; El-Sharief, A. M. Sh.; Mohamed, Sh. I. Bulletin of the Chemical Society of Japan, 75(4), 801-811; 2002
  203.  Naproxen in heterocyclic chemistry: Novel syntheses of triazoles, triazolothiadiazines, triazolothiadiazoles, and triazolothiadiazepine bearing an asymmetric carbon atom and radiostability of the biologically active compounds. Ammar, Y. A.; Ghorab, M. M.;. El-Sharief, A. M. Sh; Mohamed, Sh. I. Heteroatom Chemistry, 13(3), 199-206; 2002
  204. Regiocontrolled synthesis of the trimeric quinone framework of conocurvone.      Emadi, Ashkan; Harwood, John S.; Kohanim, Sahar; Stagliano, Kenneth W. Organic Letters, 4(4), 521-524; 2002 .
  205. Vicarious nucleophilic substitution of hydrogen (VNS) in 1,4-naphthoquinone derivatives-competition between VNS and vinylic nucleophilic substitution (SNV).      Makosza, Mieczyslaw; Nizamov, Shamil.    Tetrahedron, 57(47), 9615-9621; 2001.
  206. Synthesis of a new polypyridinic highly conjugated ligand with electron-acceptor properties.      Diaz, R.; Reyes, O.; Francois, A.; Leiva, A. M.; Loeb, B. Tetrahedron Letters, 42(37), 6463-6467; 2001.
  207. Sonochemical chloro-oxidation of phenols using HCl-H2O2.      Bhatkhande, B. S.; Adhikari, M. V.; Samant, S. D.    Ultrasonics Sonochemistry, 9(1), 31-35; 2002
  208. Synthesis and antifungal activity of some new miscellaneous s-triazoles.      Ghorab, M. M.; El-Sharief, A. M. Sh.; Ammar, Y. A.; Mohamed, Sh. I. Phosphorus, Sulfur and Silicon and the Related Elements, 173, 223-233; 2001
  209. Synthesis of 2-alkoxy 1,4-naphthoquinone derivatives as antiplatelet, antiinflammatory, and antiallergic agents.      Lien, Jin-Cherng; Huang, Li-Jiau; Teng, Che-Ming; Wang, Jih-Pyang; Kuo, Sheng-Chu. Chemical & Pharmaceutical Bulletin, 50(5), 672-674; 2002
  210. Efficient Synthesis of 'Redox-Switched' Naphthoquinone Thiol-Crown Ethers and Their Biological Activity Evaluation.      Huang, Sheng-Tung; Kuo, Hsien-Shou; Hsiao, Chiao-Long; Lin, Yuh-Ling. Bioorganic & Medicinal Chemistry, 10(6), 1947-1952; 2002.
  211. Naturalization and modification of natural colors of flowers. I. Naphthofuroquinolinedione dyes.      Boscornea, Cristian; Pasolea, Florin; Tarabasanu Mihaila, Corneliu; Boscornea, Corina. Revista de Chimie (Bucharest, Romania), 53(5), 394-403; 2002
  212. The synthesis of third-order optical nonlinear organic polyheterocyclic materials.      Gao, Jian Rong; Xiang, Bin; Shan, Wei Guang; Huang, Ming; Cheng, Lu Bai. Chinese Chemical Letters, 13(7), 609-612; 2002
  213.  Color reactions between trialkylamines and naphthoquinones.      Kallmayer, H.-J.; Thierfelder, B.   Pharmazie, 57(7), 456-459; 2002(C and Br)
  214. Reaction of 2,3-dichloro-1,4-naphthoquinone with some active methylene compounds in different basic media.      Hammam, A. S.; Fandy, R. F.; Hassan, M. A.  Chemistry of Heterocyclic Compounds (New York, NY, United States)(Translation of Khimiya Geterotsiklicheskikh Soedinenii), 38(4), 400-405; 2002
  215.  Reaction of some trialkylamine drugs with 2,3-dichloro-1,4-naphthoquinone.      Kallmayer, H.-J.; Thierfelder, B.    Pharmazie, 57(9), 648-649; 2002
  216. Synthesis and photochemical behavior of donor-acceptor systems obtained from chloro-1,4-naphthoquinone attached to trans-aminostilbenes.      Sutovsky, Y.; Likhtenshtein, G. I.; Bittner, S.    Tetrahedron, 59(16), 2939-2945; 2003
  217.  Reactions between isopropyl-alkylamines and 2,3-dichloro-1,4-naphthoquinone and 2,3-dichloro-1,4-naphthoquinone/acetaldehyde.      Kallmayer, H.-J.; Thierfelder, B.    Pharmazie, 58(2), 104-107; 2003
  218. An efficient and facile synthesis of substituted cinnoline and benzo[h]cinnoline derivatives.      Gomaa, Mohsen Abdel-Motaal. Tetrahedron Letters, 44(17), 3493-3496; 2003.
  219. Some new nitrogen bridgehead heterocyclic quinone cyanine dyes.      Koraiem, A. I. M.; El-Maghraby, M. A.; Abu-El-Hamd, R. M.; Gomaa, M. M.    Aswan Science & Technology Bulletin, 21, 8-21; 2002
  220. Synthesis and cytotoxicity evaluation of 2-amino- and 2-hydroxy-3-ethoxycarbonyl-N-substituted-benzo[f]indole-4,9-dione derivatives.      Lee, Hyun-Jung; Suh, Myung-Eun; Lee, Chong-Ock.    Bioorganic & Medicinal Chemistry, 11(7), 1511-1519; 2003.
  221. Synthesis and cytotoxicity of 6,11-Dihydro-pyrido- and 6,11-Dihydro-benzo[2,3-b]phenazine-6,11-dione derivatives.      Kim, Young-Shin; Park, Se-Young; Lee, Hyun-Jung; Suh, Myung-Eun; Schollmeyer, Dieter; Lee, Chong-Ock. Bioorganic & Medicinal Chemistry, 11(8), 1709-1714; 2003.
  222. Reaction of benzoquinones and naphthoquinones with 1,8-diamino-3,6-dioxanonane and with 1,11-diamino-3,6,9-trioxaundecane.      Machocho, Alex K.; Win, Thida; Grinberg, Sarina; Bittner, Shmuel. Tetrahedron Letters, 44(29), 5531-5534; 2003.
  223. Epoxidation of quinones with urea hydrogen peroxide.      Valderrama, Jaime A.; Gonzalez, M. Florencia; Torres, Cristian. Heterocycles, 60(10), 2343-2348; 2003
  224.  Study of a reaction between 2,3-dichloro-1,4-naphthoquinone and N,N'-diphenyl thiourea involving an EDA adduct as intermediate.      Datta, Kakali; Mukherjee, Asok K. Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 60A(7), 1641-1647; 2004
  225. 2-Oxiranecarbonitriles in the synthesis of linked quinono heterocyclic derivatives.      Volmajer, Julija; Toplak, Renata; Bittner, Shmuel; Majcen Le Marechal, Alenka. ARKIVOC (Gainesville, FL, United States),  (14), 49-61; 2003
  226. Synthesis of original benzo[g]quinoxaline-5,10-diones by bis-SRN1 methodology.      Remusat, Vincent; Terme, Thierry; Gellis, Armand; Rathelot, Pascal; Vanelle, Patrice.    Journal of Heterocyclic Chemistry, 41(2), 221-225; 2004
  227. Effect of Methoxyl Group Position on the Regioselectivity of Ammonia Substitution Reactions Involving 3,3'-Dichloro-2,2'-binaphthoquinones.      Stagliano, Kenneth W.; Lu, Zhenhai; Emadi, Ashkan; Harwood, John S.; Harwood, Cynthia A.    Journal of Organic Chemistry, 69(15), 5128-5131; 2004
  228. Synthesis and biological activity of 1,4-naphthoquinone derivatives, Part II.      Zoorob, H. H.; Berghot, M. A.; Abou-Elzahab, M. M.; Amer, F. A.    Mansoura Science Bulletin, A: Chemistry, 29(2), 129-142; 2002
  229.  Synthesis and cytotoxicity evaluation of pyridin[2,3-f]indole-2,4,9-trione and benz[f]indole-2,4,9-trione derivatives.      Lee, Hyun-Jung; Park, So-Young; Kim, Jin Sung; Song, Hyun Min; Suh, Myung-Eun; Lee, Chong-Ock.    Bioorganic & Medicinal Chemistry, 11(22), 4791-4796; 2003Synthesis of naphtho[2,3-b]furan-4,9-diones having a trifluoromethyl group under conditions of phase-transfer catalysis.      Davydov, D. V.; Beletskaya, I. P. Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii), 40(1), 134-136; 2004
  230. DABCO-Assisted coupling of some activated olefins and 2,3-dihalo-1,4-naphthoquinones and conversion to the anthraquinone derivatives.      Lee, Chang Hoon; Lee, Kee-Jung.    Synthesis,  (12), 1941-1946; 2004Palladium-catalyzed cross-coupling reaction of organobismuth compounds with aryl and alkenyl chlorides.      Yamazaki, Osamu; Tanaka, Toshifumi; Shimada, Shigeru; Suzuki, Yohichi; Tanaka, Masato. Synlett,  (11), 1921-1924; 2004
  231. Synthesis, in vitro and in vivo activity of benzophenone-based inhibitors of steroid sulfatase.      Hejaz, Hatem A. M.; Woo, L. W. Lawrence; Purohit, Atul; Reed, Michael J.; Potter, Barry V. L.    Bioorganic & Medicinal Chemistry, 12(10), 2759-2772; 2004
  232. Reaction of chloronaphthoquinones with phenylhydrazones as azaenamines in pyridine.      Berghot, M. A.; Badawy, D. S.  Chemical Papers, 57(5), 342-349; 2003
  233. Synthesis of N-quinonyltaurines.      Gorohovsky, S.; Temtsin-Krayz, G.; Bittner, S.    Amino Acids, 24(3), 281-287; 2003
  234. New access to the chemistry of piperonylidinyl-4-[2.2]-paracyclophanylamine and some electron -deficients.      El-Shaieb, Kamal M.    Journal of the Chinese Chemical Society (Taipei, Taiwan), 51(2), 321-325; 2004
  235. Phthalazinone in heterocyclic synthesis: Synthesis of some s-triazole, s-triazolothiadiazine, s-triazolothiadiazine, and s-triazolothiadiazole derivatives as pharmaceutical interest.      Abd El-Baset Hassanien, Abu Zeid.    Phosphorus, Sulfur and Silicon and the Related Elements, 178(9), 1987-1997; 2003
  236.  Novel Fused D-A Dyad and A-D-A Triad Incorporating Tetrathiafulvalene and p-Benzoquinone.      Dumur, Frederic; Gautier, Nicolas; Gallego-Planas, Nuria; Sahin, Yuecel; Levillain, Eric; Mercier, Nicolas; Hudhomme, Pietrick; Masino, Matteo; Girlando, Alberto; Lloveras, Vega; Vidal-Gancedo, Jose; Veciana, Jaume; Rovira, Concepcio. Journal of Organic Chemistry, 69(6), 2164-2177; 2004
  237. Syntheses of hitherto unknown thiazole, ylidene and pyridinethione derivatives having a piperidin-1-yl moiety and their use as antimicrobial agents.      El-Gaby, Mohamed Sayed A.    Journal of the Chinese Chemical Society (Taipei, Taiwan), 51(1), 125-134; 2004
  238. Solid-phase synthesis of 2-amino-3-chloro-5- and 8-nitro-1,4-naphthoquinones: a new and general colorimetric test for resin-bound amines.      Blackburn, Christopher. Tetrahedron Letters, 46(9), 1405-1409; 2005
  239. Process for preparation of naphthoquinonothiazole derivatives as organic third-order non-linear optical materials.      Gao, Jianrong; Sheng, Weijian; Xiang, Bin; Shan, Weiguang; Cheng, Lubai. Faming Zhuanli Shenqing Gongkai Shuomingshu, 1440966, 10 Sep 2003
  240.  Process for preparation of bisnaphthotetrathiafulvalene derivatives as organic non-linear optical materials.      Gao, Jianrong; Shan, Weiguang; Xiang, Bin; Huang, Min; Cheng, Lubai. Faming Zhuanli Shenqing Gongkai Shuomingshu, 1415612, 07 May 2003
  241.  Synthesis and biological activity of carnosine derivative of 1,4-naphthoquinone.      El Idrissi, A.; Zhurakhlvska, L. R.; Marintsova, N. H.; Taras, T. M.; Novikov, V. P.    Medichna Khimiya, 6(3), 139-140; 2004
  242. Studies on Charge-Transfer Complexes of 2,3-Dicyano-1,4-naphthoquinone with Some Ring and N-Substituted Anilines.      Neelgund, Gururaj M.; Budni, M. L. Monatshefte fuer Chemie, 135(11), 1395-1407; 2004
  243.  Synthesis of natural carnosine derivative of 1,4-naphthoquinone and it's antihypoxic effect.      El Idrissi, A.; Novikov, V. P. Farmatsevtichnii Zhurnal (Kiev),  (2), 40-44; 2004
  244. A stereoselective synthesis of spiro-dioxolanes via the multicomponent reaction of dicarbomethoxycarbene, aldehydes and 1,2- or 1,4-diones.      Nair, Vijay; Mathai, Sindhu; Mathew, Smitha C.; Rath, Nigam P.  Tetrahedron, 61(11), 2849-2856; 2005
  245.  A direct one-pot synthesis of naphtho[2,3-b]furan-4,9-dione derivatives via C,O-dialkylation of -dicarbonyl compounds by 2,3-dichloro-1,4-naphthoquinones.      Hu, Hua-You; Zhu, Ye; Wang, Lei; Xu, Jian-Hua. Synthesis,  (10), 1605-1610; 2005
  246. Interaction of 2,3-dichloro-1,4-naphthoquinone with n-butylamine in halocarbon solvents.      Neelgund, Gururaj M.; Budni, M. L. Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 61A(8), 1729-1735; 2005
  247. Preparation of diamino quinone amides that modulate the levels of gene expression in cellular systems.      Padia, Janak K.; O'Brien, Sean; Lu, Jiemin; Pikul, Stanislaw. U.S. Pat. Appl. Publ., 2005032794, 10 Feb 2005
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  249. Base catalyzed synthesis of novel fused imidazoles from N-vinyl-1H-imidazole.      Aly, Ashraf A.    Zeitschrift fuer Naturforschung, B: Chemical Sciences, 60(1), 106-112; 2005
  250. Ligand Induced Stereoisomers Revealed in Copper(II) Complex of Nitrolawsone Oxime: EPR and Electronic Spectral Studies.      Rane, S.; Khan, E.; Khursheed, Ah.; Salunke-Gawali, S. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 35(5), 343-353; 2005
  251. Design, synthesis, and biological evaluation of novel naphthoquinone derivatives with CDC25 phosphatase inhibitory activity.      Brun, Marie-Priscille; Braud, Emmanuelle; Angotti, Delphine; Mondesert, Odile; Quaranta, Muriel; Montes, Matthieu; Miteva, Maria; Gresh, Nohad; Ducommun, Bernard; Garbay, Christiane. Bioorganic & Medicinal Chemistry, 13(16), 4871-4879; 2005
  252. Sulfur-containing derivatives of 1,4-naphthoquinone. Part 1. Disulfide synthesis.      Stasevych, Maryna V.; Plotnikov, Maxym Yu.; Platonov, Mykola O.; Sabat, Svitlana I.; Musyanovych, Rostyslav Ya.; Novikov, Volodymyr P. Heteroatom Chemistry, 16(3), 205-211; 2005
  253.  Synthesis, acute toxicity, and antihypoxic and antiischemic activity of new amino acid derivatives of 1,4-naphthoquinone.      Zhurakhivskaya, L. R.; Komarovskaya-Porokhnyavets, E. Z.; Marintsova, N. G.; Novikov, V. P.; Gubitskaya, I. I.; Stepanyuk, G. I.; Sheremeta, R. O.; Tenditnaya, O. M.; Makonchuk, D. Yu.; Lysun, V. M. Farmatsevtichnii Zhurnal (Kiev, Ukraine),  (3), 67-73; 2005
  254. Preparation of naphthoquinone derivatives as PI3 kinase inhibitors for treatment of cancer.      Chang, Junbiao; Xie, Weilin; Wang, Lei. Faming Zhuanli Shenqing Gongkai Shuomingshu, 1587255, 02 Mar 2005
  255. A novel all-organic chemical and electrochemical fluorescent switch.      Illos, R. A.; Harlev, E.; Bittner, S.    Tetrahedron Letters, 46(48), 8427-8430; 2005
  256. Synthesis of some new biologically active 1,2,4-triazoles, triazolothiadiazoles, triazolothaidiazines, triazolothiadiazepine bearing sulfonamide moiety.      Al-Sehemi, A. G. Chemistry (Rajkot, India), 2(5), 139-145; 2005
  257. Reaction of enamines of the 1,2,3,4-tetrahydrobenzo[f]isoquinoline series with 2,3-dichloro-1,4-naphthoquinone.      Polygalova, N. N.; Mikhailovskii, A. G.; Gein, V. L.; Vakhrin, M. I.    Chemistry of Heterocyclic Compounds (New York, NY, United States), 41(2), 258-259; 2005
  258. Simple Electrooptical Sensors for Inorganic Anions.      Anzenbacher, Pavel, Jr.; Palacios, Manuel A.; Jursikova, Karolina; Marquez, Manuel. Organic Letters, 7(22), 5027-5030; 2005
  259. Naphthofuroquinone derivatives: DNA topoisomerase-I inhibition and cytotoxicity.      Cho, Heeyeong; Park, Su-Jin; Lee, Kee-In. Bulletin of the Korean Chemical Society, 26(11), 1829-1832; 2005
  260. A 24-Crown-8 Bearing Naphthalene and Naphthoquinone Chromophores.      Hogan, Conor F.; Hutchison, James A.; Ghiggino, Kenneth P.; Langford, Steven J.; Latter, Melissa J.; Lau, Vei-Lin; Murali, Venghatraghavan. Supramolecular Chemistry, 17(7), 513-519; 2005
  261. Synthesis of some new spiro naphtho[2,3-d][1,3]dithiole-4,9-dione derivatives.      El-Shafie, A. K.; Soliman, A. M.; Sultan, A. A.; Abd-Alla, E. Journal of Heterocyclic Chemistry, 43(1), 133-137; 2006
  262. Preparation of 2-hydroxy-3-(4-pyridyl)-1,4-naphthoquinone.      Xu, Wei; Zou, Zhenguang; Lu, Yinxiang. Faming Zhuanli Shenqing Gongkai Shuomingshu, 1775757, 24 May 2006
  263. Palladium-catalyzed amination of 2,3-dichloro-1,4-naphthoquinone with nitroarylamines.      Wang, Xiao-Lei; Zheng, Xiu-Fang; Reiner, John.    Synlett,  (6), 942-944; 2006
  264. Process for preparation of 2,3-dichloro-1,4-naphthalenedione.      Xu, Guanghui.  Faming Zhuanli Shenqing Gongkai Shuomingshu, 1733678, 15 Feb 2006
  265. Regiocontrolled synthesis and HIV inhibitory activity of unsymmetrical binaphthoquinone and trimeric naphthoquinone derivatives of conocurvone.      Stagliano, Kenneth W.; Emadi, Ashkan; Lu, Zhenhai; Malinakova, Helena C.; Twenter, Barry; Yu, Min; Holland, Louis E.; Rom, Amanda M.; Harwood, John S.; Amin, Ronak; Johnson, Allison A.; Pommier, Yves. Bioorganic & Medicinal Chemistry, 14(16), 5651-5665; 2006
  266. Reductive heterocyclization of 2,3-dichloro-1,4-naphthoquinone into naphtho[2,3-f][1,2,3,4,5]pentathiepine-6,11-diol under the action of sodium hydrosulfide in DMF.      Polonik, S. G.; Dmitrenok, P. S.; Makhan'kov, V. V.; Anufriev, V. F.  Russian Journal of Organic Chemistry, 42(2), 302-303; 2006
  267.  Naphthofuroquinone derivatives: Inhibition of receptor tyrosine kinases.      Lee, Kee-In; Park, Youmie; Park, Su-Jin; Hwang, Jung-Hwan; Lee, Sung-Jin; Kim, Gun-Do; Park, Woo-Kyu; Lee, Sunghou; Jeong, Daeyoung; Kong, Jae-Yang; Kang, Hee-Kyoung; Cho, Heeyeong. Bioorganic & Medicinal Chemistry Letters, 16(3), 737-742; 2006
  268. Charge-transfer interaction of 4,13-diamino[2.2]paracyclophane with -acceptors.      El-Shaieb, Kamal M.; Mourad, Aboul-Fetouh E.; Hopf, Henning.    ARKIVOC (Gainesville, FL, United States),  (2), 193-200; 2006
  269. Design, synthesis, and biological evaluation of 1,2,3-trisubstituted-1,4-dihydrobenzo[g]quinoxaline-5,10-diones and related compounds as antifungal and antibacterial agents.      Tandon, Vishnu K.; Yadav, Dharmendra B.; Maurya, Hardesh K.; Chaturvedi, Ashok K.; Shukla, Praveen K. Bioorganic & Medicinal Chemistry, 14(17), 6120-6126; 2006
  270. A convenient synthesis of 2-formyl-1,4,5,8-tetramethoxynaphthalene.      Xu, De-Feng; Guan, Peng-Jian; Li, Shao-Shun.    Journal of Chemical Research,  (12), 779-780; 2006
  271.  α-Vinylation of Haloquinones with Methyl Acrylate and MVK under Baylis-Hillman Reaction Conditions Lee, Seung Won; Lee, Chang Hoon; Lee, Kee-Jung  Bulletin of the Korean Chemical Society, 27(5), 769-772; 2006
  272. New cytotoxic furoquinones obtained from terpenyl-1,4-naphthoquinones and 1,4-anthracenediones.      Miguel del Corral, Jose M.; Castro, M. Angeles; Oliveira, Alaide B.; Gualberto, Simone A.; Cuevas, Carmen; San Feliciano, Arturo.    Bioorganic & Medicinal Chemistry, 14(21), 7231-7240; 2006
  273. Synthesis of benzo[f]indole-4,9-dione and benzo[b]carbazole-6,11-dione derivatives via one-pot sequential C,N-dialkylation of enaminones of -diketones and ketoesters by 2,3-dichloronaphthoquinone.      Hu, Hua-You; Liu, Yun; Ye, Miao; Xu, Jian-Hua. Synlett,  (12), 1913-1917; 2006
  274. Study on synthesis of 2,3-dichloro-1,4-naphthoquinone.      Cao, Xiao-qun; Liu, Xin; Cheng, Yue-shan.   Jingxi Yu Zhuanyong Huaxuepin, 14(3/4), 16-17; 2006
  275. Quinone-Annulated N-Heterocyclic Carbene-Transition-Metal Complexes: Observation of -Backbonding Using FT-IR Spectroscopy and Cyclic Voltammetry.      Sanderson, Matthew D.; Kamplain, Justin W.; Bielawski, Christopher W.    Journal of the American Chemical Society, 128(51), 16514-16515; 2006
  276. N-aryl-and N-vinyldiaza-18-crown-6: Synthesis and complexing ability.      Sazonov, P. K.; Artamkina, G. A.; Beletskaya, I. P. Russian Journal of Organic Chemistry, 42(3), 438-447; 2006
  277.  Process for preparation of naphtho[2,3-e][1,4,2]oxazaphosphinane derivatives for treatment of tumor.      Chen, Ruyu; Wang, Bin.  Faming Zhuanli Shenqing Gongkai Shuomingshu, 1858056, 08 Nov 2006
  278. Process for preparation of benzonaphthodithiino-thianthrene-hexone as third-order nonlinear organic optical material.      Gao, Jianrong; Cai, Zhibin; Sheng, Weijian; Jia, Jianhong; Xiang, Bin. Faming Zhuanli Shenqing Gongkai Shuomingshu, 1884282, 27 Dec 2006
  279. Naphtho[2,3-b][1,4]-thiazine-5,10-diones and 3-substituted-1,4-dioxo-1,4-dihydronaphthalen-2-yl-thioalkanoate derivatives: Synthesis and biological evaluation as potential antibacterial and antifungal agents.      Tandon, Vishnu K.; Maurya, Hardesh K.; Yadav, Dharmendra B.; Tripathi, Ashutosh; Kumar, Manish; Shukla, Praveen K. Bioorganic & Medicinal Chemistry Letters, 16(22), 5883-5887; 2006
  280. Collection of Czechoslovak Chemical Communications, 71(1), 59-76; 2006
  281. Reaction products of arylethenyl benzofuranyl ketones and their antimicrobial activity.      Micky, J. A. A.; Saleh, N. M.; Mohamed, S. M.; Mohamed, S. A.; Salem, M. M.    Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 45B(6), 1579-1583; 2006
  282. Synthesis, cytotoxicity, and DNA topoisomerase II inhibitory activity of benzofuroquinolinediones.      Rhee, Hee-Kyung; Park, Hyen Joo; Lee, Sang Kook; Lee, Chong-Ock; Choo, Hea-Young Park. Bioorganic & Medicinal Chemistry, 15(4), 1651-1658; 2007
  283. Synthesis of polycyclic indolizine derivatives via one-pot tandem reactions of N-ylides with dichloro substituted-unsaturated carbonyl compounds.      Liu, Yun; Hu, Hua-You; Liu, Qing-Jian; Hu, Hong-Wen; Xu, Jian-Hua. Tetrahedron, 63(9), 2024-2033; 2007
  284.  Synthesis of eight-, nine-, and ten-membered, nitrogen-containing quinone-fused heterocycles.      Yerushalmi, Sarit; Lemcoff, N. Gabriel; Bittner, Shmuel Synthesis, (2), 239-242; 2007.
  285. Quinone antitumor compounds, particularly 1,4-anthraquinones and their derivatives, process for their preparation, and their uses.      Molina Orden, Maria Teresa; Honghao, Sun; Taliansky Chamudis, Sandra; Carnero Moya, Amancio; Blanco Rodriguez, Fernando; Moneo Ocana, Maria Victoria. PCT Int. Appl., 2007026041, 08 Mar 2007 ( Cl and Br)
  286. Synthesis and In Vitro Cytotoxicity Evaluation of Novel Naphthindolizinedione Derivatives. Defant, Andrea; Guella, Graziano; Mancini, Ines  Archiv der Pharmazie (Weinheim, Germany), 340(3), 147-153; 2007
  287.  The 1,4-naphthoquinone scaffold in the design of cysteine protease inhibitors.  Valente, Cláudia; Moreira, Rui; Guedes, Rita C.; Iley, Jim; Jaffar, Mohammed; Douglas Kenneth T. Bioorganic & Medicinal Chemistry, 15(15), 5340-5350; 2007
  288.   Rhodanine in Fused-Heterocycles Syntheses. Mourad;  Aboul-Fetouh E.; Hassan;  Alaa A.; Aly, Ashraf A.;  Mohamed, Nasr K.; Ali, Bahaa A. Phosphorus, Sulfur and Silicon and the Related Elements, 182(2), 321-331; 2007
  289.   Benzo- and naphthoimidazoxadiazolediene, naphthobisthiazole as well as naphthothiazine derivatives from 1-acylthiosemicarbazides. Hassan, Alaa A.; Mourad, Aboul Fetouh E.; Zied, Ashraf H. Abou ARKIVOC (Gainesville, FL, United States),  (1), 222-235; 2007
  290.  3-Benzoyl-1,2-diphenyl-1H-benz[f]indole-4,9-dione.  Liu, Y.;  Lu, Z.-F.;  Ye, M.;  Zhang, Y.;  Xu; J.-H.  Acta Crystallographica, Section E: Structure Reports Online, E63(5), o2066-o2067; 2007
  291.  A simple and convenient procedure for the synthesis of naphthoquinone fused cyclic alpha-aminophosphoryl chloride.  Wang, Bin; Miao, Zhiwei; Chen, Ruyu Heteroatom Chemistry, 18(4), 359-362; 2007
  292. 3-Acetyl-1-(4-chlorophenyl)-2-methylbenzo[f]indole-4,9-dione.  Fun, H.-K.; Chantrapromma, S.;  Liu, Y.;  Xu, J.-H. Acta Crystallographica, Section E: Structure Reports Online, E63(5), o2314-o2316; 2007
  293.  2-Aminothiophenol as building blocks for novel heterocycles. El-Shaieb, K. M. Journal of Sulfur Chemistry, 28(2), 223-229; 2007
  294. Hecheng Huaxue, 15(1), 16-19; 2007
  295. Facile and efficient synthesis of 1,4-benzodiazepines from 1,4-naphthoquinons. Tandon, Vishnu K.; Maurya, Hardesh K.  Heterocycles 76(2), 1007-1010; 2008
  296.  Facile and Efficient Synthesis of Novel Oxazine, Oxazepine and Phenoxazine of Chromenones Fused with 1,4-Naphthoquinone. Tandon, Vishnu K.; Maurya, Hardesh K.  Heterocycles 77(1), 611-615; 2009
  297. 2,3-Disubstituted-1,4-naphthoquinones, 12H-benzo[b]phenothiazine-6,11-diones andrelated compounds:  Synthesis and Biological evaluation as potential antiproliferative and antifungal agents. Tandon, Vishnu K.; Maurya, Hardesh K.;  Tripathi, Ashutosh; ShivaKeshava, G.B.;  Shukla, Praveen K.; Srivastava, Pallavi; Panda Dulal   European Journal of Medicinal Chemistry 44(3), 1086-1092; 2009.
  298. Design, synthesis and biological evaluation of novel nitrogen and sulfur containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents. Tandon, Vishnu K.; Maurya, Hardesh K.; Mishra, Nripendra N.; Shukla, Praveen K. European Journal of Medicinal Chemistry 44(8), 3130-3137; 2009.
  299.  ‘On water’: unprecedented nucleophilic substitution and addition reactions with 1,4-quinones in aqueous suspension. Tandon, Vishnu K.; Maurya, Hardesh K.  Tetrahedron Letters 50, 5896-5902; 2009.
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