Aza-annulation as a versatile approach to the synthesis of non-benzodiazepene compounds for the treatment of sleep disorders

Tetrahedron Letters

Volumn 38, Issue 49, 1997, Pages 8475-8478

  Benovsky, Petr ^a   Stille, John R ^b  

^a MICHIGAN STATE UNIVERSITY   (United States)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENAMINE; HETEROCYCLIC COMPOUND; THIOPHENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; OXIDATION; REACTION ANALYSIS; SLEEP DISORDER;

EID: 0030696892     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10297-0     Document Type: Article

References (34)

1. (a) Fischer, U.; Schneider, F.; Widmer, U. Eur. Pat, EP183994 (CA: 1986, 107, 134200b).
2. (b) Fischer, U.; Mohler, H, Schneider, F.; Widmer, U. Helv. Chim. Acta 1990, 73, 763.
3. (c) Scherschlicht, R. R.; Widmer, U. Eur. Pat., EP496274 (CA: 1992, 117, 191707c).
4. (d) Spurr, P. R. Tetrahedron Lett. 1995, 36, 2745.
5. For a review on the subject of aza-annulation, see: Stille, J. R.; Barta, N. S. Studies in Natural Products Chemistry: Stereoselective Synthesis: Atta-ur-Rahman, Ed.; New York, 1996; Vol. 18, pp 315-389.
6. Beholz, L. G.; Benovsky, P.; Ward, D. L.; Barta, N. S.; Stille, J. R. J. Org. Chem. 1997, 62, 1033.
7. (a) Paulvannan, K.; Schwarz, J. B.; Stille, J. R. Tetrahedron Lett. 1993, 34, 215.
8. (b) Paulvannan, K.; Stille, J. R. Tetrahedron Lett. 1993, 34, 6673.
9. (c) Paulvannan, K.; Stille, J. R. J. Org. Chem. 1994, 59, 1613.
10. (d) Cook, G. R.; Beholz, L. G.; Stille, J. R. Tetrahedron Lett. 1994, 35, 1669.
11. (e) Cook, G. R.; Beholz, L. G.; Stille, J. R. J. Org. Chem. 1994, 59, 3575.
12. (a) Paulvannan, K.; Stille, J. R. Tetrahedron Lett. 1993, 34, 8197.
13. (b) Barta, N. S.; Brode, A.; Stille, J. R. J. Am. Chem. Soc. 1994, 116, 6201.
14. Wasserman, H. H.; Ives, J. L. J. Org. Chem. 1985, 50, 3573.
15. 13C NMR, IR, and HRMS data were obtained for all reaction products.
16. Gittos, M. W.; Robinson, M. R.; Verge, J. P.; Davies, R. V.; Iddon, B.; Suschitzky, H. J. Chem. Soc. Perkin Trans. 1 1976, 33.
17. 7
18. 7
19. Aza-annulation reactions with enamines related in structure to 15, but which lack the ester substituent, have been studied: (a) Kametani, T.; Terasawa, H.; Ihara, M. J. Chem. Soc., Perkin Trans. I 1976, 2547.
20. (b) Kametani, T.; Terasawa, H.; Ihara, M.; Fukumoto, K. Heterocycles 1977, 6, 37.
21. (c) Kametani, T.; Suzuki, Y.; Ihara, M. Can. J. Chem. 1979, 57, 1679.
22. (d) Kametani, T.; Suzuki, Y.; Terasawa, H.; Ihara, M. J. Chem. Soc., Perkin Trans. I 1979, 1211.
23. (e) Ihara, M.; Noguchi, K.; Ohsawa, T.; Fukumoto, K.; Kametani, T. Heterocycles 1982, 19, 1829.
24. (f) Bhattacharjya, A.; Bhattacharya, P. K.; Pakrashi, S. C. Heterocycles 1983, 20, 2397.
25. Aza-annulation reactions with enamines related in structure to 24, but which lack the ester substituent, have been studied: (a) Kametani, T.; Kanaya, N.; Hino, H.; Huang, S.-P.; Ihara, M. Heterocycles 1980, 14, 1771.
26. (b) Danieli, B.; Lesma, G.; Palmisano, G. J. Chem. Soc., Chem. Commun. 1980, 109.
27. (c) Danieli, B.; Lesma, G.; Palmisano, G. Gazz. Chim. Ital. 1981, 111, 257.
28. (d) Kametani, T.; Ohsawa, T.; Ihara, M. J. Chem. Soc., Perkin Trans. I 1981, 1563.
29. (e) Kametani, T.; Kanaya, N., Ihara, M. Heterocycles 1981, 16, 925.
30. (f) Kametani, T.; Kanaya, N.; Hino, H.; Huang, S.-P.; Ihara, M. J. Chem. Soc., Perkin Trans. I 1981, 3168.
31. (g) Calabi, L.; Danieli, B.; Lesma, G.; Palmisano, G. Tetrahedron Lett. 1982, 23, 2139.
32. (h) Danieli, B.; Lesma, G.; Palmisano, G.; Tollari, S. Synthesis 1984, 353.
33. (i) Hua, D. H.; Bharathi, S. N.; Takusagawa, F.; Tsujimoto, A.; Panangadan, J. A. K.; Hung, M.-H.; Bravo, A. A.; Erpelding, A. M. J. Org. Chem. 1989, 54, 5659.
34. (j) Hua, D. H.; Bharathi, S. N.; Panangadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998.