One-step assembly of carbamoyl-substituted heteroannelated [1,4]thiazepines

Journal of Organic Chemistry

Volumn 71, Issue 7, 2006, Pages 2811-2819

  Ilyn, Alexey P ^a   Loseva, Marina V ^a   Vvedensky, Vladimir Y ^b   Putsykina, Elena B ^a   Tkachenko, Sergey E ^b   Kravchenko, Dmitri V ^a   Khvat, Alexandr V ^b   Krasavin, Mikhail Y ^b   Ivachtchenko, Alexandre V ^a  

^a Chemical Diversity Research Institute   (Russian Federation)

^b CHEMDIV INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMOYL; CARBOXAMIDES; THIAZEPINES; UGI CONDENSATION;

CONDENSATION; NITROGEN COMPOUNDS; SULFUR; SYNTHESIS (CHEMICAL);

AMINES;

3 OXO 1,4 THIAZEPINE 5 CARBOXAMIDE; 5 OXO 1,4 THIAZEPINE 3 CARBOXAMIDE; THIAZEPINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; POLYMERIZATION; STRUCTURE ANALYSIS;

CARBAMATES; MOLECULAR STRUCTURE; STEREOISOMERISM; THIAZEPINES;

EID: 33645531098     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052640w     Document Type: Article

References (32)

1. (a) Skiles, J. W.; Suh, J. T.; Williams, B. E.; Menard, P. R.; Barton, J. N.; Love, B.; Jones, H.; Neiss, E. S.; Schwab, A.; Mann, W. S. J. Med. Chem. 1986, 29, 784-796.
2. (b) Crescenza, A.; Botta, M.; Corelli, F.; Santini, A.; Tafi, A. J. Org. Chem. 1999, 64, 3019-3025.
3. (c) Umemiya, H.; Fukasawa, H.; Ebisawa, M.; Eyrolles, L.; Kawachi, E.; Eisenmann, G.; Gronemeyer, H.; Hashimoto, Y.; Shudo, K.; Kagechika, H. J. Med. Chem. 1997, 40, 4222-4234.
4. (d) Venkatesan, A. M.; Gu, Y.; Dos Santos, O.; Abe, T.; Agarwal, A.; Yang, Y.; Petersen, P. J.; Weiss, W. J.; Mansour, T. S.; Nukaga, M.; Hujer, A. M.; Bonomo, R. A.; Knox, J. R. J. Med. Chem. 2004, 47, 6556-6568.
5. (a) Malli, R.; Frieden, M.; Trenker, M.; Graier, W. F. J. Biol. Chem. 2005, 280, 12114-12122.
6. (b) Neamati, N.; Turpin, J. A.; Winslow, H. E.; Christensen, J. L.; Williamson, K.; Orr, A.; Rice, W. G.; Pommier, Y.; Garofalo, A.; Brizzi, A.; Campiani, G. J. Med. Chem. 1999, 42, 3334-3341.
7. (c) Maruenda, H.; Johnson F. J. Med. Chem. 1995, 38, 2145-2151.
8. (d) Garofalo, A.; Campiani, G.; Fiorini, I.; Nacci, V. Farmaco 1993, 48, 275-283.
9. (a) Boulware, S. L.; Bronstein, J. C.; Nordby, E. C.; Weber, P. C. Antivir. Res. 2001, 51, 111-125.
10. (b) Cale, A. D.; Gero, T. W.; Walker, K. R.; Lo, Y. S.; Welstead, W. J.; Jaques, L. W.; Johnson, A. F.; Leonard, C. A.; Nolan, J. C.; Johnson, D. N. J. Med. Chem. 1989, 32, 2178-2199.
11. (c) Nakao, T.; Tanaka, H.; Yamato, H.; Akagi, T.; Takehara, S. US 5141930; Chem. Abstr. 1992, 116, 194290b.
12. (d) Schlosser, K. M.; Krasutsky, A. P.; Hamilton, H. W.; Reed, J. E.; Sexton, K. Org. Lett. 2004, 6, 819-821.
13. (a) Nagarajan, K.; Arya, V. P.; Parthasarathy, T. N.; Shenoy, S. J.; Sahah, R. K.; Kulkarni, Y. S. Indian J. Chem. 1981, 20, 672-679.
14. (b) Nefzi, A.; Ong, N. A.; Giulianotti, M. A.; Ostresh, J. M.; Houghten, R. A. Tetrahedron Lett. 1999, 40, 4939-4942.
15. (c) Hirai, K.; Iwano, Y.; Mikoshiba, I.; Homma, H. Annu. Rept. Sankyo Res. Lab. 1992, 44, 141-150.
16. (d) Czollner, L.; Szilagyi, G.; Lango, J. Magy. Kem. Folyoir. 1998, 94, 332-335.
17. (e) Khatana, S. S.; Boschelli, D. H.; Kramer, J. B.; Connor, D. T.; Barth, H.; Stoss, P. J. Org. Chem. 1996, 61, 6060-6062.
18. (a) Ugi, I.; Lohberger, S.; Karl, R. The Passerini and Ugi Reactions. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 1083-1109.
19. (b) Domling, A.; Ugi, I. Angew. Chem. 2000, 39, 3168-3210.
20. (a) Ley, S. V.; Taylor, S. J. Bioorg. Med. Chem. Lett. 2002, 12, 1813-1816.
21. (b) Short, K. M.; Mjalli, A. M. M. Tetrahedron Lett. 1997, 38, 359-362.
22. (c) Zhang, J.; Jacobson, A.; Rusche, J. R.; Herlihy, W. J. Org. Chem. 1999, 64, 1074-1076.
23. (d) Marcaccini, S.; Pepino, R.; Torroba, T.; Miguel, D.; Garcia-Valverde, M. Tetrahedron Lett. 2002, 43, 8591-8593.
24. Marcaccini, S.; Miguel, D.; Torroba, T.; Garcia-Valverde, M. J. Org. Chem. 2003, 68, 3315-3318.
25. (a) Ilyn, A. P.; Trifilenkov, A. S.; Kuzovkova, J. A.; Kutepov, S. A.; Nikitin, A. V.; Ivachtchenko, A. V. J. Org. Chem. 2005, 70, 1478-1481.
26. (b) Ilyn, A. P.; Kuzovkova, J. A.; Potapov, V. V.; Shkirando, A. M.; Kovrigin, D. I.; Tkachenko, S. E.; Ivachtchenko, A. V. Tetrahedron Lett. 2005, 46, 881-884.
27. Cagniant P.; Briola M.-M.; Kirsch G. C. R. Acad. Sci. 1977, C285, 21-24.
28. Deng, H.; Konopelski, J. P. Org. Lett., 2001, 3, 301-304.
29. Lavergne, O.; Lesueur-Ginot, L.; Pla Rodas, F.; Kasprzyk, P. G.; Pommier, J.; Demarquay, D.; Pre'vost, G.; Ulibarri, G.; Rolland, A.; Schiano-Liberatore, A.-M.; Harnett, J.; Pons, D.; Camara, J.; Bigg, D. C. H. J. Med. Chem. 1998, 41, 5410-5419.
30. Barreiro, E. J.; Camara, C. A.; Verli, H.; Brazil-Ma's, L.; Castro, N. G.; Cintra, W. M.; Aracava, Y.; Rodrigues, C. R.; Fraga, C. A. M. J. Med. Chem. 2003, 46, 1144-1152.
31. Majo, V. J.; Perumal, P. T. J. Org. Chem. 1996, 61, 6523-6525.
32. Blank, B.; DiTullio, N. W.; Owings, F. F.; Deviney, L.; Miao, C. K.; Saunders: H. L. J. Med. Chem. 1977, 20, 572-576.