A convenient synthesis of 1-acyl indolizines by 1,3-dipolar cycloaddition reactions of pyridinium ylides and α,β-unsaturated aldehydes or ketones in the presence of tetrakis-pyridine cobalt dichromate

Synthetic Communications

Volumn 27, Issue 8, 1997, Pages 1395-1403

  Zhang, Xuechun ^a   Cao, Weili ^a   Wei, Xudong ^a   Hu, Hongwen ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLIZINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030959037     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708006070     Document Type: Article

References (25)

1. For reviews see: a) Prostakov, N.S. and Batibaev, O.B. Russ. Chem. Rev. 1975, 44, 748; b) Uchida, T. and Matsumoto, K. Synthesis 1976, 209; c) Swinbourne, F.T., Hunt, J. and Klinkert, K. in "Advances in Heterocyclic Chemistry," eds. Katritzky, A.R. and Boulton, A.J., Academic Press, New York, 1978, Vol. 23, pp. 103-482.
2. For reviews see: a) Prostakov, N.S. and Batibaev, O.B. Russ. Chem. Rev. 1975, 44, 748; b) Uchida, T. and Matsumoto, K. Synthesis 1976, 209; c) Swinbourne, F.T., Hunt, J. and Klinkert, K. in "Advances in Heterocyclic Chemistry," eds. Katritzky, A.R. and Boulton, A.J., Academic Press, New York, 1978, Vol. 23, pp. 103-482.
3. For reviews see: a) Prostakov, N.S. and Batibaev, O.B. Russ. Chem. Rev. 1975, 44, 748; b) Uchida, T. and Matsumoto, K. Synthesis 1976, 209; c) Swinbourne, F.T., Hunt, J. and Klinkert, K. in "Advances in Heterocyclic Chemistry," eds. Katritzky, A.R. and Boulton, A.J., Academic Press, New York, 1978, Vol. 23, pp. 103-482.
4. For example: a) Padwa, A., Austin, D.J., Precedo, L. and Zhi, L. J. Org. Chem. 1993, 58, 1144; b) Matsumoto, K., Ikemi, Y. and Konishi, H. Heterocycles 1984, 22, 701; c) Leonate, C. and Zugravescu, I. Tetrahedron Lett. 1972, 2029.
5. For example: a) Padwa, A., Austin, D.J., Precedo, L. and Zhi, L. J. Org. Chem. 1993, 58, 1144; b) Matsumoto, K., Ikemi, Y. and Konishi, H. Heterocycles 1984, 22, 701; c) Leonate, C. and Zugravescu, I. Tetrahedron Lett. 1972, 2029.
6. For example: a) Padwa, A., Austin, D.J., Precedo, L. and Zhi, L. J. Org. Chem. 1993, 58, 1144; b) Matsumoto, K., Ikemi, Y. and Konishi, H. Heterocycles 1984, 22, 701; c) Leonate, C. and Zugravescu, I. Tetrahedron Lett. 1972, 2029.
7. a) Hayashi, Y., Nakamura, H. and Nazaki, H. Bull. Chem. Soc. Jpn. 1973, 46, 667;
8. b) Basketter, N.S. and Plunkett, A.O. J. Chem. Soc., Chem. Commun. 1973, 188;
9. c) Matsumoto, K., Uchida, T. and Paquette, L.A. Synthesis 1979, 746.
10. a) Huisgen, R., Grashey, R. and Steingruber, E. Tetrahedron Lett. 1963, 1441;
11. b) Hendrick, C.A., Ritchie, E. and Taylor, W.C. Aust. J. Chem. 1967, 20, 2467 and 2476;
12. c) Kakei, A. and Ito, S. Bull Chem. Soc. Jpn. 1974, 47, 938;
13. d) Frohlich, J. and Kronhke, F. Chem. Ber. 1971, 104, 1621.
14. a) Thesing, J. and Müller, U.A. Angew. Chem. 1965, 68, 338 and 577;
15. b) Thesing, J. and Müller, A. Chem. Ber. 1957, 90, 711.
16. Acheson, R.M., Bite, M.G. and Cooper, M.W. J. Chem. Soc., Perkin Trans 1 1976, 1908;
17. Sasaki, T. and Yoshioka, Y. Bull. Chem. Soc. Jpn. 1971, 44, 803;
18. Miki, Y., Hiroishi, Y., Hachiken, H. and Takemura, S. J. Heterocycl. Chem. 1991, 28, 45.
19. Tamura, Y., Sumida, Y. and Ikeda, M. J. Chem. Soc., Perkin Trans 1 1973, 2091.
20. Tamura, Y., Sumida, Y., Haruki, S. and Ikeda, M. J. Chem. Soc., Perkin Trans 1 1975, 575.
21. Tominaga, Y., Ichihara, Y., Mori, T., Kamio, C. and Hosomi, A. J. Heterocycl. Chem. 1990, 27, 263.
22. Nugent, R.A. and Murphy, M. J. Org. Chem. 1987, 52, 2206.
23. Scholtz, R. Chem. Ber. 1912, 45, 739.
24. Wei, X., Hu, Y., Li, T. and Hu, H. J. Chem. Soc., Perkin Trans 1 1993, 2487.
25. Hu, Y. and Hu, H. Synth. Commun. 1992, 22, 1491.