2-Phosphaindolizines via 1,5-electrocyclization

Tetrahedron Letters

Volumn 40, Issue 8, 1999, Pages 1565-1568

  Bansal, Raj K ^a   Surana, Anushka ^a   Gupta, Neelima ^a  

^a UNIVERSITY OF RAJASTHAN   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2 PHOSPHAINDOLIZINE DERIVATIVE; INDOLIZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0033582690     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02645-8     Document Type: Article

References (23)

1. Schmidpeter, A. In Comperihensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V. Eds.; Elsevier: Oxford, 1996; vol. 3, pp. 709-738 and vol. 4, pp. 771-827.
2. Schmidpeter, A. In Comperihensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V. Eds.; Elsevier: Oxford, 1996; vol. 3, pp. 709-738 and vol. 4, pp. 771-827.
3. Schmidpeter, A.; Karaghiosoff, K. Heterophospholes. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M.; Scherer, O. J. Eds.; Thieme: Stuttgart, 1990; pp. 258-286.
4. Schmidpeter, A.; Karaghiosoff, K. Azaphospholes. In Rings, Clusters and Polymers of Main Group and Transition Elements; Roesky, H. W. Ed.; Elsevier: Amsterdam, 1989; pp. 307-343.
5. Bansal, R. K.; Karaghiosoff, K.; Schmidpeter, A. Tetrahedron, 1994, 50, 7675.
6. Bansal, R. K.; Karaghiosoff, K.; Gandhi, N.; Schmidpeter, A. Synthesis, 1995, 361.
7. Bansal, R. K.; Mahnot, R.; Panday G.; Gupta R. J. Indian Chem. Soc., 1994, 71, 415.
8. Bansal, R. K.; Karaghiosoff, K.; Gupta, N.; Schmidpeter, A.; Spindler, C. Chem. Ber. 1991, 124, 475.
9. Bansal, R. K.; Kabra, V.; Gupta, N.; Karaghiosoff, K. Indian J. Chem. 1992, 31B, 254.
10. Gupta, N.; Jain, C. B.; Heinicke, J.; Bharatiya, N.; Bansal, R. K.; Jones, P.G. Heteroatom Chem. 1998, 9, 333.
11. Märkl, G.; Pflaum, S. Tetrahedron Lett. 1987, 28, 1511.
12. Bergsträßer, U.; Hoffmann, A.; Regitz, M. Tetrahedron Lett. 1992, 33, 1049.
13. Karaghiosoff, K.; Mahnot, R.; Cleve, C.; Gandhi, N.; Bansal, R. K.; Schmidpeter, A. Chem. Ber., 1995, 128, 581.
14. Bansal, R. K.; Gupta, N.; Kabra, V.; Spindler, C.; Karaghiosoff, K.; Schmidpeter, A. Heteroatom Chem. 1992, 3, 359.
15. Gupta, N.; Jain, C. B.; Heinicke, J.; Bansal, R. K.; Jones, P. G. Euro. J. Chem. 1998, 1079.
16. Bansal, R. K.; Gupta, N.; Surana, A.; Bharatiya, N. unpublished results.
17. Schmidpeter, A.; Jochem, G. Tetrahedron Lett. 1992, 33(4), 471.
18. Bansal, R. K.; Gupta, N.; Gupta, R.; Pandey, G.; Agarwal, M. Phosphorus Sulphur and Silicon 1996, 112, 121.
19. Taylor, E. C.; Turchi, I. J. Chem. Rev. 1979, 79, 2.
20. 2 (30ml) was stirred at r.t. under nitrogen atmosphere for 4 days. The solvent was thereafter removed under reduced pressure and the residue left was extracted with diethyl ether (2 × 10ml). 2-Phosphaindolizine 4e separated on keeping the concentrated extract in refrigerator.
21. 3N (1.95g, 19.2mmol) slowly at r.t. with stirring. After 5 hours the solvent was evaporated and the residue extracted with diethyl ether (2 × 50ml). Orange crystals of 4a separated on leaving the combined and concentrated ether extract in the refrigerator.
22. 2 (15ml) at r.t. After 5 hours the solvent was evaporated and the residue was worked up as in 20.
23. Karaghiosoff, K.; Schmidpeter, A. Phosphorus Sulfur 1988, 36, 217.