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- Title
Synthesis of pyrrolidines and tetrahydro-1H-azepines from 4-aryl-1-benzoyl(ethoxycarbonyl)methyl-1-methyl-1,2,3,6-tetrahydropyridinium halides.
- Authors
Soldatova, S. A.; Gimranova, G. S.; Mamyrbekova, Zh. A.; Polyanskii, K. B.; Akbulatov, S. V.; Soldatenkov, A. T.
- Abstract
4-Aryl-1,2,3,6-tetrahydropyridinium quaternary salts which have a benzoylmethyl or ethoxycarbonylmethyl group on atom N-1 generate N-ylides when heated in the presence of NaH and they can rearrange in situ with contraction or expansion of the six-membered heterocycle to give substituted pyrrolidines (as a result of a [2,3]-sigmatropic rearrangement) or 1H-tetrahydroazepine derivatives (via Stevens rearrangement). The presence of an aryl substituent at position C-4 in the tetrahydropyridine ring allows to avoid the formation of elimination products and changes the direction of the reaction towards the preparation of the tetrahydroazepines.
- Subjects
HALIDES; SALTS; ATOMS; YLIDES; PYRROLIDINE
- Publication
Chemistry of Heterocyclic Compounds, 2007, Vol 43, Issue 11, p1420
- ISSN
0009-3122
- Publication type
Article
- DOI
10.1007/s10593-007-0219-2