Studies on the configurational stability of 3-(2-piperidyl)indoles

Journal of Organic Chemistry

Volumn 61, Issue 11, 1996, Pages 3878-3882

  Amat, Mercedes ^a   Hadida, Sabine ^a   Llor, Núria ^a   Sathyanarayana, Swargam ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343416220     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952251+     Document Type: Article

References (16)

1. Bosch, J.; Rubiralta, M.; Domingo, A.; Bolós, J.; Linares, A.; Minguillón, C.; Amat, M.; Bonjoch, J. J. Org. Chem. 1985, 50, 1516.
2. Amat, M.; Sathyanarayana, S.; Hadida, S.; Bosch, J. Tetrahedron Lett. 1994, 35, 7123.
3. The biogenetic numbering is used for tetracyclic structures: Le Men, J; Taylor, W. I. Experientia 1965, 21, 508.
4. Compounds 1-7 are racemic. Compounds 3a-7a have been drawn in the same enantiomeric series as the natural products: 3a and 4a as both the uleine-type and the Strychnos alkaloids with the aspidospermatan skeletal type and 5a-7a as the Strychnos alkaloids with the strychnan skeletal type.
5. Gràcia, J.; Casamitjana, N.; Bonjoch, J.; Bosch, J. J. Org. Chem. 1994, 59, 3939.
6. The presence of a 16-oxo substituent seems to preclude the epimerization: Jackson, A.; Wilson, N. D. V.; Gaskell, A. J.; Joule, J. A. J. Chem. Soc. C 1969, 2738.
7. For a similar ring opening under alkaline conditions, see: Bosch, J.; Amat, M.; Domingo, A. Heterocycles 1984, 22, 561.
8. Kisakürek, M. V.; Leeuwenberg, A. J. M.; Hesse, M. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1983; Vol. 1, Chapter 5.
9. For related epimerizations in octahydropyrido[3,2-c]carbazoles bearing an acyl substituent on the piperidine nitrogen, see: (a) Gallagher, T.; Magnus, P. Tetrahedron 1981, 37, 3889.
10. (b) Natsume, M.; Utsunomiya, I. Heterocycles 1982, 17, 111.
11. 4. The absolute configuration of 8 was determined by X-ray crystallography.
12. (b) Amat, M.; Llor, N.; Bosch, J. Tetrahedron Lett. 1995, 35, 2223.
13. Albright, J. D.; Snyder, H. R. J. Am. Chem. Soc. 1959, 81, 2239.
14. The preparation of some enantiomerically pure 1-(benzene-sulfonyl)-3-(2-piperidyl)indoles has recently been described and no epimerization at the piperidine 2-position has been reported: Miguel, D.; Diez, A.; Blache, Y.; Luque, J.; Orozco, M.; Remuson, R.; Gelas-Mialhe, Y.; Rubiralta, M. Tetrahedron 1995, 51, 7527.
15. Amat, M.; Linares, A.; Bosch, J. J. Org. Chem. 1990, 55, 6299.
16. Van Tamelen, E. E.; Knapp, G. G. J. Am. Chem Soc. 1955, 77, 1860.