A facile and stereoselective azepine-ring formation at the periphery of pyridone and pyrido[1,2-a]pyrimidone systems via intramolecular imine and carbonyl ene reactions

Tetrahedron

Volumn 52, Issue 41, 1996, Pages 13081-13096

  Noguchi, Michihiko ^a   Mizukoshi, Takashi ^a   Kakehi, Akikazu ^b  

^a YAMAGUCHI UNIVERSITY   (Japan)

^b SHINSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AZEPINE DERIVATIVE; PYRIDO[1,2 A]PYRIMIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030272313     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00771-5     Document Type: Article

References (20)

1. (1) Inazumi, T.; Harada, E.; Mizukoshi, T.; Kuroki, R.; Kakehi, A.; Noguchi, M. J. Chem. Soc., Perkin Trans. 1 1994, 565.
2. (2) Kuroki, R.; Akao, R.; Inazumi, T.; Noguchi, M. Tetrahedron 1994, 50, 1063.
3. (3) (a) Oppolzer, W.; Snieckus, V. Angew. Chem., Int. Ed. Engl. 1978, 17, 476.
4. (b) Snider, B. B.; Phillips, G. B. J. Org. Chem. 1983, 49, 183.
5. (4) (a) Motoki, S.; Watanabe, T.; Saito, T. Tetrahedron Lett. 1989, 30, 189.
6. (b) Choi, S. S.-M.; Kirby, G. W.; Mahajan, M. P. J. Chem. Soc., Chem. Commun. 1990, 138.
7. (c) Saito, T.; Watanabe, T.; Kitazawa, S.; Hayashi, Y.; Motoki, S. J. Chem. Soc., Perkin Trans. 1 1991, 959.
8. (d) Saito, T.; Shundo, Y.; Kitazawa, S.; Motoki, S. J. Chem. Soc., Chem. Commun. 1992, 600. Also see Taber, D. F.; 'Intramolecular Diels-Alder and Alder Ene Reactions,' Springer Verlag, New York, 1984, ch 3.
9. (d) Saito, T.; Shundo, Y.; Kitazawa, S.; Motoki, S. J. Chem. Soc., Chem. Commun. 1992, 600. Also see Taber, D. F.; 'Intramolecular Diels-Alder and Alder Ene Reactions,' Springer Verlag, New York, 1984, ch 3.
10. (5) Examples of the carbonyl and imine ene reactions catalyzed by Lewis acids were found in reviews; (a) Snider, B. B. Acc. Chem. Res. 1980, 13, 426.
11. (b) Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1984, 23, 876.
12. (c) Borzilleri, R. M.; Weinreb, S. M. Synthesis 1995, 347.
13. (6) Acid catalysts gave substantially no effects on the azepine-ring formation in our systems: Noguchi, M.; Mizukoshi, T.; Nishimura, S. unpublished results.
14. (7) The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 2EZ, UK.
15. (8) Noguchi, M.; Mizukoshi, T.; Uchida, T.; Kuroki, Y. in the succeeding paper.
16. (9) George, T.; Mehta, D. V.; Dabholkar, D. A. J. Org. Chem. 1971, 36, 2192.
17. (10) Butt, M. A.; Elvidge, J. A. J. Chem. Soc. 1963, 4483.
18. (11) TEXAN TEXRAY, Structure Analysis Package, Molecular Structures Corporation, 1985.
19. (12) Gilmore, C. J. J. Appl. Crystallogr. 1984, 77, 42.
20. (13) Johnson, C. K. ORTEP II, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, 1976.