Synthesis of sulfur-containing heterocyclic compounds by cyclocondensationof acetylenic derivatives of anthraquinone with sodium sulfide

Arkivoc

Volumn 2003, Issue 13, 2003, Pages 87-100

  Shvartsberg, Mark S ^a   Ivanchikova, Irena D ^a  

^a INSTITUTE OF CHEMICAL KINETICS AND COMBUSTION   (Russian Federation)

Author keywords

Acetylenic derivatives of anthraquinone; Anthrathiophenediones; Anthrathiopyrantriones; Cyclocondensation

Indexed keywords

1 (3 HYDROXY 3 METHYLBUTYNYL)ANTHRAQUINONE; 1 CHLORO 2 (1 OXO 3 PHENYLPROPYNYL)ANTHRAQUINONE; 1 CHLORO 2 (1 OXOHEPT 2 YNYL)ANTHRAQUINONE; 1 CHLORO 2 (4 HYDROXY 4 METHYL 1 OXOPENTYNYL)ANTHRAQUINONE; 1 CHLORO 2 (4 METHYL 1 OXOHEX 4 EN 2 YNYL)ANTHRAQUINONE; 1 CHLORO 2 [3 (1 CYCLOHEXENYL) 1 OXOPROPYNYL]ANTHRAQUINONE; 1 PHENYLETHYNYLANTHRAQUINONE; 2 (1 CYCLOHEXENYL)ANTHRA[1,2 B]THIOPYRAN 4,7,12 TRIONE; 2 (1 CYCLOHEXENYL)ANTHRA[2,3 B]THIOPYRAN 4,6,12 TRIONE; 2 (1 HYDROXY 1 METHYLETHYL)ANTHRA[1,2 B]THIOPYRAN 4,7,12 TRIONE; 2 (1 HYDROXY 1 METHYLETHYL)ANTHRA[2,1 B]THIOPHENE 6,11 DIONE; 2 (1 METHYLPROP 1 ENYL)ANTHRA[1,2 B]THIOPYRAN 4,7,12 TRIONE; 2 BUTYLANTHRA[1,2 B]THIOPYRAN 4,7,12 TRIONE; 2 CHLORO 3 (1 OXO 3 PHENYLPROPYNYL)ANTHRAQUINONE; 2 CHLORO 3 [3 (1 CYCLOHEXENYL) 1 OXOPROPYNYL]ANTHRAQUINONE; 2 PHENYLANTHRA[1,2 B]THIOPYRAN 4,7,12 TRIONE; 2 PHENYLANTHRA[2,1 B]THIOPHENE 6,11 DIONE; 2 PHENYLANTHRA[2,3 B}THIOPYRAN 4,6,12 TRIONE; ALCOHOL; ANTHRA[1,2 B]THIOPHENE 6,11 DIONE DERIVATIVE; ANTHRA[2,1 B]THIOPHENE 6,11 DIONE; ANTHRAQUINONE DERIVATIVE; HETEROCYCLIC COMPOUND; ORGANOSULFUR DERIVATIVE; SODIUM SULFIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; CYCLOCONDENSATION; DRUG SYNTHESIS; HEATING; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 3242708721     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (34)

1. Yue, D.; Larock, R.C. J. Org. Chem. 2002, 67, 1905.
2. McDonald, F.E.; Burova, S.A.; Huffman, L.G. Synthesis 2000, 970.
3. Tolstikova, T. G.; Davydova, V. A.; Shul'ts, E. E.; Vafina, G. F.; Safarova, G. M.; Zarudii, F. A.; Lazareva, D. N.; Tolstikov, G. A. Khim.-Farm. Zh. 1990, 24, 27 (Russ.).
4. Kita, Y.; Kirihara, M.; Sekihachi, J.; Okunaka, R.; Sasho, M.; Mohri, Sh.; Honda, T.; Akai, Sh.; Tamura, Y.; Shimooka, K. Chem. Pharm. Bull. 1990, 38, 1836.
5. Ohba, Y.; Murakami, Y.; Sone, T.; Awano, H. J. Heterocycl. Chem. 1997, 34, 781.
6. Deng, X.; Liebeskind, L. S. J. Am. Chem. Soc., 2001, 123, 7703.
7. Sall, D.J.; Bastian, J.A.; Briggs, S.L.; Buben, J.A.; Chirgadze, N.Y.; Clawson, D.K.; Denney, M.L.; Giera, D.D.; Gifford-Moore, D.S.; Harper, R.W.; Hauser, K.L.; Klimkowski, V.J.; Kohn, T.J.; Lin, H. Sh.; McCowan, J.R.; Palkowitz, A.D.; Smith, G.F.; Takeuchi, K.; Thrasher, K.J.; Tinsley, J.M.; Utterback, B.G., Yan, S.-Ch. B.; Zhang, M. J. Med. Chem. 1997, 40, 3489.
8. Bradley, D.Y., Godfrey, A.G., Schmid, C.R. Tetrahedron Lett. 1999, 40, 5155.
9. Piskunov, A.V.; Shvartsberg, M.S. Mendeleev Commun. 1995, 155.
10. Shvartsberg, M.S.; Ivanchikova, I.D.; Lebedeva, N.I. Tetrahedron Lett. 2000, 41, 5757.
11. Shvartsberg, M.S.; Piskunov, A.V.; Mzhelskaya, M.A.; Moroz, A.A. Izv. Akad. Nauk, Ser. Khim. 1993, 1423; Russ. Chem. Bull. 1993, 42, 1357.
12. Shvartsberg, M.S.; Piskunov, A.V.; Mzhelskaya, M.A.; Moroz, A.A. Izv. Akad. Nauk, Ser. Khim. 1993, 1423; Russ. Chem. Bull. 1993, 42, 1357.
13. Shvartsberg, M.S.; Barabanov, I.I.; Fedenok, L.G. Mendeleev Commun. 1997, 98.
14. Shvartsberg, M.S.; Ivanchikova, I.D.; Vasilevsky, S.F. Tetrahedron Lett. 1994, 35, 2077.
15. Mzhelskaya, M.A.; Moroz, A.A.; Shvartsberg, M.S. Izv. Akad. Nauk Ser. Khim. 1991, 1656; Bull. Acad. Sci. USSR, Div. Chem. Sci. 1991, 40, 1469.
16. Mzhelskaya, M.A.; Moroz, A.A.; Shvartsberg, M.S. Izv. Akad. Nauk Ser. Khim. 1991, 1656; Bull. Acad. Sci. USSR, Div. Chem. Sci. 1991, 40, 1469.
17. Shvartsberg, M.S.; Ivanchikova, I.D.; Fedenok, L.G. Tetrahedron Lett. 1994, 35, 6749.
18. Shvartsberg, M.S.; Ivanchikova, I.D. Tetrahedron Lett. 2000, 41, 771.
19. Barabanov, I.I.; Ivanchikova, I.D.; Shvartsberg, M.S. Mendeleev Commun. 2000, 188.
20. Fedenok, L.G.; Barabanov, I.I.; Ivanchikova, I.D. Tetrahedron 2001, 57, 1331.
21. Larock, C.R.; Yue, D. Tetrahedron Lett. 2001, 42, 6011.
22. Flynn, B.L.; Verdier-Pinard, P.; Hamel, E. Org. Lett. 2001, 5, 651.
23. Malte, A.M.; Castro, C.E. J. Am. Chem. Soc. 1967, 89, 6770.
24. Lendel, V.G.; Pakh, V. J.; Petrus, V.V.; Kijak, M.Yu.; Migalina, Yu.V. Khim. Geterotsikl. Soedin. 1990, 1331 (Russ.).
25. Smirnov-Zamkov I.V.; Zborovsky, Yu.L. Zh. Organ. Khim. 1977, 667 (Russ).
26. Sakamoto, T.; Kondo, Y.; Watanabe, R.; Yamanaka, H. Chem. Pharm. Bull. 1986, 34, 2719.
27. Gorelik, M.V. Chemistry of Anthraquinones and Their Derivatives, Moscow, Khimiya, 1983, 296pp.
28. Piskunov, A.V.; Moroz, A.A.; Shvartsberg, M.S. Izv. Akad. Nauk SSSR, Ser. Khim. 1986, 864; Bull. Acad. Sci. USSR, Div. Chem. Sci. 1986, 35, 785.
29. Piskunov, A.V.; Moroz, A.A.; Shvartsberg, M.S. Izv. Akad. Nauk SSSR, Ser. Khim. 1986, 864; Bull. Acad. Sci. USSR, Div. Chem. Sci. 1986, 35, 785.
30. Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1980, 45, 3061.
31. JP 61/224992. JPN. - C.A. 1987, 106, 137013h.
32. Piskunov, A.V.; Moroz, A.A.; Shvartsberg, M.S. Izv. Akad. Nauk SSSR, Ser. Khim. 1987, 828; Bull. Acad. Sci. USSR, Div. Chem. Sci. 1987, 36, 755.
33. Piskunov, A.V.; Moroz, A.A.; Shvartsberg, M.S. Izv. Akad. Nauk SSSR, Ser. Khim. 1987, 828; Bull. Acad. Sci. USSR, Div. Chem. Sci. 1987, 36, 755.
34. Zanina, A.S.; Shergina, S.I.; Sokolov, I.E.; Kotlyarevsky, I.L Izv. Akad. Nauk SSSR, Ser. Khim. 1981, 1158 (Russ.).