Preparation of New Nitrogen-Bridged Heterocycles. 43.1 Synthesis and Reaction of 5aH-Pyrido[1,2-d][1,3,4]thiadiazepine Derivatives

Journal of Organic Chemistry

Volumn 62, Issue 22, 1997, Pages 7788-7793

  Kakehi, Akikazu ^a   Ito, Suketaka ^a   Ishida, Fumihito ^a   Tominaga, Yoshinori ^b  

^a SHINSHU UNIVERSITY   (Japan)

^b NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007834374     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971066o     Document Type: Article

References (23)

1. For part 42 of this series, see Kakehi, A.; Ito, S.; Hashimoto, Y. Bull. Chem. Soc. Jpn. 1996, 69, 1769.
2. (a) Kakehi, A.; Ito, S.; Hakui, J. Chem. Lett. 1992, 777.
3. (b) Kakehi, A.; Ito, S. Heterocycles 1993, 36, 1195.
4. (c) Kakehi, A.; Ito, S.; Hakui, J. Bull. Chem. Soc. Jpn. 1993, 66, 3475.
5. (d) Kakehi, A.; Ito, S.; Mitani, M.; Kanaoka, M. Bull. Chem. Soc. Jpn. 1994, 67, 1646.
6. (e) Kakehi, A.; Ito, S.; Fujita, S. Bull. Chem. Soc. Jpn. 1995, 68, 1473.
7. (a) Kakehi, A.; Ito, S.; Watanabe, K. Bull. Chem. Soc. Jpn. 1980, 53, 1775.
8. (b) Yoshida, H.; Urushibata, K.; Ogata, T. Bull. Chem. Soc. Jpn. 1983, 56, 1561.
9. Kakehi, A.; Ito, S.; Ishida, F.; Tominaga, Y. Heterocycles, 1995, 41, 2657.
10. Kakehi, A.; Ito, S.; Nagata, K.; Kinoshita, N.; Kakinuma, N. Chem. Pharm. Bull. 1987, 35, 156.
11. For the crystal data for compound 7h, see ref 4.
12. (a) Okamoto, T.; Hirobe, M.; Yabe, E. Chem. Pharm. Bull. 1966, 14, 506.
13. (b) Sasaki, T.; Kanematsu, K.; Kakehi, A. J. Org. Chem. 1972, 36, 2978.
14. (c) Sasaki, T.; Kanematsu, K.; Kakehi, A.; Ito, G. J. Chem. Soc., Perkin Trans. 1 1973, 2089.
15. (d) Tamura, Y.; Sumida, Y.; Miki, Y.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1975, 406.
16. This situation is quite opposite to the relation (see ref 2b) in the interaction between the 7-methyl group and 5-substituent in 7-methyl-10aH-pyrido[1,2-d][1,4]thiazepine derivatives.
17. According to the MM2 calculation for these pyrido[1,2-d][1,3,4]thiadiazepine derivatives 5 and 5′, the angular conformation D is more favorable than the planar one E. This fact may suggest a reason for the inaccessibility and ready rearrangement of 6-unsubstituted pyrido[1,2-d][1,3,4]thiadiazepine intermediates 5, because subsequent rearrangement starts from this comformation D.
18. Though our ring system is not normal di-π-methane ring system such as 2,5-cyclohexadien-1-one, we used this word from the similarities of the apparent electron demand and the structural transformation. For di-π-methane rearrangement, see Schaffner K. Adv. Photochem. 1966 4, 81. Kropp P. J. Org. Photochem. 1967, 7, 1.
19. Though our ring system is not normal di-π-methane ring system such as 2,5-cyclohexadien-1-one, we used this word from the similarities of the apparent electron demand and the structural transformation. For di-π-methane rearrangement, see Schaffner K. Adv. Photochem. 1966 4, 81. Kropp P. J. Org. Photochem. 1967, 7, 1.
20. Whether this reaction proceeds successfully or not is largely dependent upon the exhaustive removal of the moisture and any nucleophiles from the reaction system.
21. 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 1EZ, UK.
22. "TEXSAN TEXRAY", Structure Analysis Package," Molecular Structure Corporation, 1985.
23. Gilmore, C. J. J. Appl. Crystallogr. 1984, 17, 42.