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[3+3] Cyclization reactions of β-nitroenamines and β-enaminonitriles with α,β-unsaturated carboxylic acid chlorides
- Source :
-
Tetrahedron . Jun2008, Vol. 64 Issue 23, p5545-5550. 6p. - Publication Year :
- 2008
-
Abstract
- Abstract: New indolizidines, quinolizidines, and octahydro-pyrido[1,2-a]azepines of lactam type were synthesized from 2-nitromethylene-pyrrolidine, -piperidine, and -hexahydroazepine, respectively, by [3+3] cyclizations with α,β-unsaturated carboxylic acid chlorides. In the case of quinolizidines, a double bond migration was observed, and explained in terms of amidity percentage. Cyanomethylene-pyrrolidine gave indolizidines of lactam type, while transformations of 1-cyanomethylene-tetrahydoisoquinoline resulted in lactams as well as ketones, when simple open-chain acid chlorides or cinnamoyl chloride were used, respectively. [Copyright &y& Elsevier]
- Subjects :
- *ORGANIC acids
*CHLORIDES
*ORGANONITROGEN compounds
*PYRROLIDINE
Subjects
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 64
- Issue :
- 23
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 32050001
- Full Text :
- https://doi.org/10.1016/j.tet.2008.03.090