A short synthesis of 2,3-di(hetero)arylpyrido[3,2-f][1,4]thiazepines

Synthesis

Volumn , Issue 8, 1996, Pages 986-990

  Couture, Axel ^a   Deniau, Eric ^a   Grandclaudon, Pierre ^a   Simion, Cristian ^a  

^a CNRS   (France)

Author keywords

2 azaallyl anions; annulation; electrocycli c reactions; O ethyl thiocarboxylates; pyrido 3,2 f 1,4 thiazepines

Indexed keywords

PYRIDO[3,2 F][1,4]THIAZEPINE DERIVATIVE; THIAZEPINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029813223     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4329     Document Type: Article

References (43)

1. Comprehensive Heterocyclic Chemistry, Katritzky, A. R.; Rees, C.W. Eds.; Pergamon Press: Oxford, 1984.
2. Krapcho, J.; Spitzmiller, E. R.; Turk, C. F. J. Med. Chem. 1963, 6, 544. Kugita, H.; Inoue, H.; Iakesaki, M.; Konda, M.; Takeo, S. Chem. Pharm. Bull. 1971, 19, 595. Sato, M.; Nagao, T.; Nakajima, H.; Kiyomoto, A. Arzneim. Forsch. 1971, 21, 1338. Ohno, S.; Izumi, K.; Mizukoshi, K.; Kato, K.; Hori, M. Chem. Pharm. Bull. 1983, 31, 1780.
3. Krapcho, J.; Spitzmiller, E. R.; Turk, C. F. J. Med. Chem. 1963, 6, 544. Kugita, H.; Inoue, H.; Iakesaki, M.; Konda, M.; Takeo, S. Chem. Pharm. Bull. 1971, 19, 595. Sato, M.; Nagao, T.; Nakajima, H.; Kiyomoto, A. Arzneim. Forsch. 1971, 21, 1338. Ohno, S.; Izumi, K.; Mizukoshi, K.; Kato, K.; Hori, M. Chem. Pharm. Bull. 1983, 31, 1780.
4. Krapcho, J.; Spitzmiller, E. R.; Turk, C. F. J. Med. Chem. 1963, 6, 544. Kugita, H.; Inoue, H.; Iakesaki, M.; Konda, M.; Takeo, S. Chem. Pharm. Bull. 1971, 19, 595. Sato, M.; Nagao, T.; Nakajima, H.; Kiyomoto, A. Arzneim. Forsch. 1971, 21, 1338. Ohno, S.; Izumi, K.; Mizukoshi, K.; Kato, K.; Hori, M. Chem. Pharm. Bull. 1983, 31, 1780.
5. Krapcho, J.; Spitzmiller, E. R.; Turk, C. F. J. Med. Chem. 1963, 6, 544. Kugita, H.; Inoue, H.; Iakesaki, M.; Konda, M.; Takeo, S. Chem. Pharm. Bull. 1971, 19, 595. Sato, M.; Nagao, T.; Nakajima, H.; Kiyomoto, A. Arzneim. Forsch. 1971, 21, 1338. Ohno, S.; Izumi, K.; Mizukoshi, K.; Kato, K.; Hori, M. Chem. Pharm. Bull. 1983, 31, 1780.
6. Husa, R. K.; Rafferty, M. F.; Hagen, T. J.; Hallinan, E. A. U.S. Patent 5304644, 1994; Chem. Abstr. 1994, 121, 134165.
7. Osawa, T.; Murooka, H.; Mira, A. JPN Patent 05271208, 1993; Chem. Abstr. 1994, 120, 245182.
8. Kakehi, S.; Ito, S. JPN Patent 0625257, 1994; Chem. Abstr. 1994, 121, 134166.
9. Brieaddy, L. W. PCT Int. Appl. WO 9516055, 1993; Chem. Abstr. 1994, 120, 164244.
10. Housley, J. R.; Jeffery, J. E.; Nichol, K. J.; Sargent, B. J. PCT Int. Appl. WO 9411360, 1994; Chem. Abstr. 1994, 121, 134167.
11. Schmidt, G.; Hargrave, K. D.; CA Patent 2024071, 1991; Chem. Abstr. 1991, 115, 208030.
12. Cale, A. D.; Gero, T. W.; Walker, K. R.; Lo, Y. S.; Welstead, Jr., W. J.; Jaques, L. W.; Johnson, A. F.; Leonard, C. A.; Nolan, J. C.; Johnson, D.N. J. Med. Chem. 1989, 32, 2178.
13. Kauffmann, T.; Eidenschink, R. Angew. Chem. 1973, 85, 583; Angew. Chem., Int. Ed. Engl. 1973, 12, 568.
14. Kauffmann, T.; Eidenschink, R. Angew. Chem. 1973, 85, 583; Angew. Chem., Int. Ed. Engl. 1973, 12, 568.
15. Gribble, G. W.; Saulnier, M. G. Tetrahedron Lett. 1980, 4137. Gribble, G. W.; Saulnier, M. G. Heterocycles 1993, 35, 151.
16. Gribble, G. W.; Saulnier, M. G. Tetrahedron Lett. 1980, 4137. Gribble, G. W.; Saulnier, M. G. Heterocycles 1993, 35, 151.
17. Güngor, T.; Marsais, F.; Quéguiner, G. J. Organomet. Chem. 1981, 215, 139. Trécourt, T.; Marsais, F.; Güngor, T.; Quéguiner, G. J. Chem. Soc., Perkin Trans. 1 1990, 2409.
18. Güngor, T.; Marsais, F.; Quéguiner, G. J. Organomet. Chem. 1981, 215, 139. Trécourt, T.; Marsais, F.; Güngor, T.; Quéguiner, G. J. Chem. Soc., Perkin Trans. 1 1990, 2409.
19. Mallet, M. J. Organomet. Chem. 1991, 406, 49.
20. Schlecker, W.; Huth, A.; Ottow, E.; Mulzer, J. Liebigs Ann. Chem. 1995, 1441.
21. Reynaud, P.; Moreau, R. C.; Samana, J. P. Bull. Soc. Chim. Fr. 1965, 3628. Bunnelle, W. H.; Mc Kinnis, B. R.; Narayanan, B. A. J. Org. Chem. 1990, 55, 768. Couture, A.; Grandclaudon, P.; Huguerre, E. Tetrahedron 1989, 45, 4153.
22. Reynaud, P.; Moreau, R. C.; Samana, J. P. Bull. Soc. Chim. Fr. 1965, 3628. Bunnelle, W. H.; Mc Kinnis, B. R.; Narayanan, B. A. J. Org. Chem. 1990, 55, 768. Couture, A.; Grandclaudon, P.; Huguerre, E. Tetrahedron 1989, 45, 4153.
23. Reynaud, P.; Moreau, R. C.; Samana, J. P. Bull. Soc. Chim. Fr. 1965, 3628. Bunnelle, W. H.; Mc Kinnis, B. R.; Narayanan, B. A. J. Org. Chem. 1990, 55, 768. Couture, A.; Grandclaudon, P.; Huguerre, E. Tetrahedron 1989, 45, 4153.
24. Kauffmann, T. Angew. Chem. 1974, 86, 715; Angew. Chem., Int. Ed. Engl. 1974, 13, 627. Vo-Quang, L.; Vo-Quang, Y. Tetrahedron Lett. 1977, 3963. Gracheva, R. A.; Potapov, V. M.; Sivov N. A. and Sivova, L. I. J. Org. Chem. USSR 1982, 17, 1963; Chem. Abstr. 1982, 96, 103745.
25. Kauffmann, T. Angew. Chem. 1974, 86, 715; Angew. Chem., Int. Ed. Engl. 1974, 13, 627. Vo-Quang, L.; Vo-Quang, Y. Tetrahedron Lett. 1977, 3963. Gracheva, R. A.; Potapov, V. M.; Sivov N. A. and Sivova, L. I. J. Org. Chem. USSR 1982, 17, 1963; Chem. Abstr. 1982, 96, 103745.
26. Kauffmann, T. Angew. Chem. 1974, 86, 715; Angew. Chem., Int. Ed. Engl. 1974, 13, 627. Vo-Quang, L.; Vo-Quang, Y. Tetrahedron Lett. 1977, 3963. Gracheva, R. A.; Potapov, V. M.; Sivov N. A. and Sivova, L. I. J. Org. Chem. USSR 1982, 17, 1963; Chem. Abstr. 1982, 96, 103745.
27. Kauffmann, T. Angew. Chem. 1974, 86, 715; Angew. Chem., Int. Ed. Engl. 1974, 13, 627. Vo-Quang, L.; Vo-Quang, Y. Tetrahedron Lett. 1977, 3963. Gracheva, R. A.; Potapov, V. M.; Sivov N. A. and Sivova, L. I. J. Org. Chem. USSR 1982, 17, 1963; Chem. Abstr. 1982, 96, 103745.
28. Kauffmann, T. Angew. Chem. 1974, 86, 715; Angew. Chem., Int. Ed. Engl. 1974, 13, 627. Vo-Quang, L.; Vo-Quang, Y. Tetrahedron Lett. 1977, 3963. Gracheva, R. A.; Potapov, V. M.; Sivov N. A. and Sivova, L. I. J. Org. Chem. USSR 1982, 17, 1963; Chem. Abstr. 1982, 96, 103745.
29. Vingiello, F. A.; Rorer, M. P.; Ogliaruso, M. A. J. Chem. Soc., Chem. Commun. 1971, 329. Nishiguchi, T.; Tochio, H.; Nabeya, A.; Iwakura, Y. J. Am. Chem. Soc. 1969, 91, 5835. Couture, A.; Deniau, E.; Simion, C.; Grandclaudon, P. Synlett 1995, 809.
30. Vingiello, F. A.; Rorer, M. P.; Ogliaruso, M. A. J. Chem. Soc., Chem. Commun. 1971, 329. Nishiguchi, T.; Tochio, H.; Nabeya, A.; Iwakura, Y. J. Am. Chem. Soc. 1969, 91, 5835. Couture, A.; Deniau, E.; Simion, C.; Grandclaudon, P. Synlett 1995, 809.
31. Vingiello, F. A.; Rorer, M. P.; Ogliaruso, M. A. J. Chem. Soc., Chem. Commun. 1971, 329. Nishiguchi, T.; Tochio, H.; Nabeya, A.; Iwakura, Y. J. Am. Chem. Soc. 1969, 91, 5835. Couture, A.; Deniau, E.; Simion, C.; Grandclaudon, P. Synlett 1995, 809.
32. Kauffmann, T.; Habersaat, K.; Koppelman, E. Chem. Ber. 1977, 110, 638. Kauffmann, T.; Busch, A.; Habersaat, K.; Koppelman, E. Chem. Ber. 983, 116, 492. Pearson, W. H. In Studies in Natural Product Chemistry, Stereoselective Synthesis, Part A; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1988; Vol. 1, p 323. Vo-Quang, L.; Gaessler, H.; Vo-Quang, Y. Angew. Chem. 1981, 93, 922; Angew. Chem., Int. Ed. Engl. 1981, 20, 880. Vo-Quang, L.; Vo-Quang, Y. J. Heterocycl. Chem. 1982, 19, 145. Dryanska, V.; Ivanov, C.; Krusteva, R. Synthesis 1984, 1038.
33. Kauffmann, T.; Habersaat, K.; Koppelman, E. Chem. Ber. 1977, 110, 638. Kauffmann, T.; Busch, A.; Habersaat, K.; Koppelman, E. Chem. Ber. 983, 116, 492. Pearson, W. H. In Studies in Natural Product Chemistry, Stereoselective Synthesis, Part A; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1988; Vol. 1, p 323. Vo-Quang, L.; Gaessler, H.; Vo-Quang, Y. Angew. Chem. 1981, 93, 922; Angew. Chem., Int. Ed. Engl. 1981, 20, 880. Vo-Quang, L.; Vo-Quang, Y. J. Heterocycl. Chem. 1982, 19, 145. Dryanska, V.; Ivanov, C.; Krusteva, R. Synthesis 1984, 1038.
34. Kauffmann, T.; Habersaat, K.; Koppelman, E. Chem. Ber. 1977, 110, 638. Kauffmann, T.; Busch, A.; Habersaat, K.; Koppelman, E. Chem. Ber. 983, 116, 492. Pearson, W. H. In Studies in Natural Product Chemistry, Stereoselective Synthesis, Part A; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1988; Vol. 1, p 323. Vo-Quang, L.; Gaessler, H.; Vo-Quang, Y. Angew. Chem. 1981, 93, 922; Angew. Chem., Int. Ed. Engl. 1981, 20, 880. Vo-Quang, L.; Vo-Quang, Y. J. Heterocycl. Chem. 1982, 19, 145. Dryanska, V.; Ivanov, C.; Krusteva, R. Synthesis 1984, 1038.
35. Kauffmann, T.; Habersaat, K.; Koppelman, E. Chem. Ber. 1977, 110, 638. Kauffmann, T.; Busch, A.; Habersaat, K.; Koppelman, E. Chem. Ber. 983, 116, 492. Pearson, W. H. In Studies in Natural Product Chemistry, Stereoselective Synthesis, Part A; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1988; Vol. 1, p 323. Vo-Quang, L.; Gaessler, H.; Vo-Quang, Y. Angew. Chem. 1981, 93, 922; Angew. Chem., Int. Ed. Engl. 1981, 20, 880. Vo-Quang, L.; Vo-Quang, Y. J. Heterocycl. Chem. 1982, 19, 145. Dryanska, V.; Ivanov, C.; Krusteva, R. Synthesis 1984, 1038.
36. Kauffmann, T.; Habersaat, K.; Koppelman, E. Chem. Ber. 1977, 110, 638. Kauffmann, T.; Busch, A.; Habersaat, K.; Koppelman, E. Chem. Ber. 983, 116, 492. Pearson, W. H. In Studies in Natural Product Chemistry, Stereoselective Synthesis, Part A; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1988; Vol. 1, p 323. Vo-Quang, L.; Gaessler, H.; Vo-Quang, Y. Angew. Chem. 1981, 93, 922; Angew. Chem., Int. Ed. Engl. 1981, 20, 880. Vo-Quang, L.; Vo-Quang, Y. J. Heterocycl. Chem. 1982, 19, 145. Dryanska, V.; Ivanov, C.; Krusteva, R. Synthesis 1984, 1038.
37. Kauffmann, T.; Habersaat, K.; Koppelman, E. Chem. Ber. 1977, 110, 638. Kauffmann, T.; Busch, A.; Habersaat, K.; Koppelman, E. Chem. Ber. 983, 116, 492. Pearson, W. H. In Studies in Natural Product Chemistry, Stereoselective Synthesis, Part A; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1988; Vol. 1, p 323. Vo-Quang, L.; Gaessler, H.; Vo-Quang, Y. Angew. Chem. 1981, 93, 922; Angew. Chem., Int. Ed. Engl. 1981, 20, 880. Vo-Quang, L.; Vo-Quang, Y. J. Heterocycl. Chem. 1982, 19, 145. Dryanska, V.; Ivanov, C.; Krusteva, R. Synthesis 1984, 1038.
38. Kauffmann, T.; Habersaat, K.; Koppelman, E. Chem. Ber. 1977, 110, 638. Kauffmann, T.; Busch, A.; Habersaat, K.; Koppelman, E. Chem. Ber. 983, 116, 492. Pearson, W. H. In Studies in Natural Product Chemistry, Stereoselective Synthesis, Part A; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1988; Vol. 1, p 323. Vo-Quang, L.; Gaessler, H.; Vo-Quang, Y. Angew. Chem. 1981, 93, 922; Angew. Chem., Int. Ed. Engl. 1981, 20, 880. Vo-Quang, L.; Vo-Quang, Y. J. Heterocycl. Chem. 1982, 19, 145. Dryanska, V.; Ivanov, C.; Krusteva, R. Synthesis 1984, 1038.
39. Bell, T. W.; Hu, L. Y. Tetrahedron Lett. 1988, 29, 4819.
40. Mayr, H.; Heigl, U. W.; Baran, J. Chem. Ber. 1993, 126, 1913.
41. Mallory, F. B.; Mallory, C. W. Org. React. 1984, 30, 1.
42. Liu, L.; Yang, B.; Katz, T. J.; Poindexter, M. K. J. Org. Chem. 1991, 56, 3769.
43. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.