A new entry to pyrano[3,2-f]indolizines via the regioselective formation of an indolizidin-7-one enamine

Heterocycles

Volumn 43, Issue 7, 1996, Pages 1391-1402

  Pollet, Olivier ^a   Cordonnier, Guy ^a   Bengourina, Chérif ^a   Randria, Clarisse ^a   Sliwa, Henri ^a  

^a UNIV LILLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0006019888     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-7368     Document Type: Article

References (28)

1. A preliminary report has been published : G. Cordonnier, C. Randria, and H. Sliwa, Tetrahedron Lett., 1994, 35, 8617.
2. P. W. Hickmott, Tetrahedron, 1982, 38, 1975.
3. H. J. Jakobsen, S. O. Lawesson, J. T. B. Marshall, G. Schroll, and D. H. Williams, J. Chem. Soc. (B), 1966, 940; S. K. Malhotra, D. F. Moakley, and F. Johnson, J. Chem. Soc., Chem. Commun., 1967, 448.
4. H. J. Jakobsen, S. O. Lawesson, J. T. B. Marshall, G. Schroll, and D. H. Williams, J. Chem. Soc. (B), 1966, 940; S. K. Malhotra, D. F. Moakley, and F. Johnson, J. Chem. Soc., Chem. Commun., 1967, 448.
5. G. V. Grishina, V. M. Potapov, S. A. Abdulganeeva, and I. A. Ivanova, Khim. Geterotsikl Soedinenii, 1983, 1510; S. A. Vartanyan and E. A. Abgaryan, Armyan. Khim. Zhur., 1984, 37, 316.
6. G. V. Grishina, V. M. Potapov, S. A. Abdulganeeva, and I. A. Ivanova, Khim. Geterotsikl Soedinenii, 1983, 1510; S. A. Vartanyan and E. A. Abgaryan, Armyan. Khim. Zhur., 1984, 37, 316.
7. G. Cordonnier and H. Sliwa, J. Heterocycl. Chem., 1987, 24, 111.
8. N. K. Hart, S. R. Johns, and J. A. Lamberton, J. Chem. Soc. (D), 1971, 460; N. K. Hart, S. R. Johns, and J. A. Lamberton, Austral J. Chem., 1972, 25, 817; T. Watanabe, Y. Nakashita, S. Katayama, and M. Yamauchi, Heterocycles, 1981, 16, 39.
9. N. K. Hart, S. R. Johns, and J. A. Lamberton, J. Chem. Soc. (D), 1971, 460; N. K. Hart, S. R. Johns, and J. A. Lamberton, Austral J. Chem., 1972, 25, 817; T. Watanabe, Y. Nakashita, S. Katayama, and M. Yamauchi, Heterocycles, 1981, 16, 39.
10. N. K. Hart, S. R. Johns, and J. A. Lamberton, J. Chem. Soc. (D), 1971, 460; N. K. Hart, S. R. Johns, and J. A. Lamberton, Austral J. Chem., 1972, 25, 817; T. Watanabe, Y. Nakashita, S. Katayama, and M. Yamauchi, Heterocycles, 1981, 16, 39.
11. O. S. Wolfbeis, Monastsh. Chem., 1982, 113, 365; G. Dannhardt, W. Meindl, S. Gussmann, S. Ajili, and T. Kappe, European J. Medicin. Chem., 1987, 22, 505.
12. O. S. Wolfbeis, Monastsh. Chem., 1982, 113, 365; G. Dannhardt, W. Meindl, S. Gussmann, S. Ajili, and T. Kappe, European J. Medicin. Chem., 1987, 22, 505.
13. F. Lions and A. M. Willison, J. Proc. Roy. Soc. New South Wales, 1940, 73, 240 (Chem. Abstr., 1940, 34, 5841); R. T. Holden and R. Raper, J. Chem. Soc., 1963, 2545; A. H. Beckett, R. G. Lingard, and A. E. Theobald, J. Medicin. Chem., 1969, 12, 563; R. V. Stevens, Y. Luh, and J. T. Sheu, Tetrahedron Lett., 1976, 3799: A. S. Howard, G. C. Gerrans, and C. A. Meerholz, Tetrahedron Lett., 1980, 21, 1373; F. D. King, Tetrahedron Lett., 1983, 24, 3281; F. D. King, J. Chem. Soc., Perkin Trans 1., 1986, 447.
14. F. Lions and A. M. Willison, J. Proc. Roy. Soc. New South Wales, 1940, 73, 240 (Chem. Abstr., 1940, 34, 5841); R. T. Holden and R. Raper, J. Chem. Soc., 1963, 2545; A. H. Beckett, R. G. Lingard, and A. E. Theobald, J. Medicin. Chem., 1969, 12, 563; R. V. Stevens, Y. Luh, and J. T. Sheu, Tetrahedron Lett., 1976, 3799: A. S. Howard, G. C. Gerrans, and C. A. Meerholz, Tetrahedron Lett., 1980, 21, 1373; F. D. King, Tetrahedron Lett., 1983, 24, 3281; F. D. King, J. Chem. Soc., Perkin Trans 1., 1986, 447.
15. F. Lions and A. M. Willison, J. Proc. Roy. Soc. New South Wales, 1940, 73, 240 (Chem. Abstr., 1940, 34, 5841); R. T. Holden and R. Raper, J. Chem. Soc., 1963, 2545; A. H. Beckett, R. G. Lingard, and A. E. Theobald, J. Medicin. Chem., 1969, 12, 563; R. V. Stevens, Y. Luh, and J. T. Sheu, Tetrahedron Lett., 1976, 3799: A. S. Howard, G. C. Gerrans, and C. A. Meerholz, Tetrahedron Lett., 1980, 21, 1373; F. D. King, Tetrahedron Lett., 1983, 24, 3281; F. D. King, J. Chem. Soc., Perkin Trans 1., 1986, 447.
16. F. Lions and A. M. Willison, J. Proc. Roy. Soc. New South Wales, 1940, 73, 240 (Chem. Abstr., 1940, 34, 5841); R. T. Holden and R. Raper, J. Chem. Soc., 1963, 2545; A. H. Beckett, R. G. Lingard, and A. E. Theobald, J. Medicin. Chem., 1969, 12, 563; R. V. Stevens, Y. Luh, and J. T. Sheu, Tetrahedron Lett., 1976, 3799: A. S. Howard, G. C. Gerrans, and C. A. Meerholz, Tetrahedron Lett., 1980, 21, 1373; F. D. King, Tetrahedron Lett., 1983, 24, 3281; F. D. King, J. Chem. Soc., Perkin Trans 1., 1986, 447.
17. F. Lions and A. M. Willison, J. Proc. Roy. Soc. New South Wales, 1940, 73, 240 (Chem. Abstr., 1940, 34, 5841); R. T. Holden and R. Raper, J. Chem. Soc., 1963, 2545; A. H. Beckett, R. G. Lingard, and A. E. Theobald, J. Medicin. Chem., 1969, 12, 563; R. V. Stevens, Y. Luh, and J. T. Sheu, Tetrahedron Lett., 1976, 3799: A. S. Howard, G. C. Gerrans, and C. A. Meerholz, Tetrahedron Lett., 1980, 21, 1373; F. D. King, Tetrahedron Lett., 1983, 24, 3281; F. D. King, J. Chem. Soc., Perkin Trans 1., 1986, 447.
18. F. Lions and A. M. Willison, J. Proc. Roy. Soc. New South Wales, 1940, 73, 240 (Chem. Abstr., 1940, 34, 5841); R. T. Holden and R. Raper, J. Chem. Soc., 1963, 2545; A. H. Beckett, R. G. Lingard, and A. E. Theobald, J. Medicin. Chem., 1969, 12, 563; R. V. Stevens, Y. Luh, and J. T. Sheu, Tetrahedron Lett., 1976, 3799: A. S. Howard, G. C. Gerrans, and C. A. Meerholz, Tetrahedron Lett., 1980, 21, 1373; F. D. King, Tetrahedron Lett., 1983, 24, 3281; F. D. King, J. Chem. Soc., Perkin Trans 1., 1986, 447.
19. F. Lions and A. M. Willison, J. Proc. Roy. Soc. New South Wales, 1940, 73, 240 (Chem. Abstr., 1940, 34, 5841); R. T. Holden and R. Raper, J. Chem. Soc., 1963, 2545; A. H. Beckett, R. G. Lingard, and A. E. Theobald, J. Medicin. Chem., 1969, 12, 563; R. V. Stevens, Y. Luh, and J. T. Sheu, Tetrahedron Lett., 1976, 3799: A. S. Howard, G. C. Gerrans, and C. A. Meerholz, Tetrahedron Lett., 1980, 21, 1373; F. D. King, Tetrahedron Lett., 1983, 24, 3281; F. D. King, J. Chem. Soc., Perkin Trans 1., 1986, 447.
20. F. Lions and A. M. Willison, J. Proc. Roy. Soc. New South Wales, 1940, 73, 240 (Chem. Abstr., 1940, 34, 5841); R. T. Holden and R. Raper, J. Chem. Soc., 1963, 2545; A. H. Beckett, R. G. Lingard, and A. E. Theobald, J. Medicin. Chem., 1969, 12, 563; R. V. Stevens, Y. Luh, and J. T. Sheu, Tetrahedron Lett., 1976, 3799: A. S. Howard, G. C. Gerrans, and C. A. Meerholz, Tetrahedron Lett., 1980, 21, 1373; F. D. King, Tetrahedron Lett., 1983, 24, 3281; F. D. King, J. Chem. Soc., Perkin Trans 1., 1986, 447.
21. T. A. Crabb, R. F.Newton, and D. Jackson, Chem. Rev., 1971, 71, 109.
22. G. Stork, A. Brizzolara, H. Landesman, J. Szmuszkovicz, and R. Terrel, J. Am. Chem. Soc., 1963, 85, 207.
23. H. Sliwa and G. Cordonnier, J. Heterocycl. Chem., 1977, 14, 169; G. Cordonnier and H. Sliwa, J. Chem. Res., 1979, S, 124, M, 1461.
24. H. Sliwa and G. Cordonnier, J. Heterocycl. Chem., 1977, 14, 169; G. Cordonnier and H. Sliwa, J. Chem. Res., 1979, S, 124, M, 1461.
25. 13
26. R. Haller and W. Hansel, Tetrahedron, 1970, 26, 2035.
27. Nmr assignments are related to the predominant regioisomer (5a) or (6a). 15. Nmr assignments are related to the mixture (8a) + (8b).
28. Nmr assignments are related to the predominant anomer which is observed alone in the initial freshly prepared sample solution.