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.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1670–1676, November, 2007.
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Soldatova, S.A., Gimranova, G.S., Mamyrbekova, Z.A. et al. Synthesis of pyrrolidines and tetrahydro-1H-azepines from 4-aryl-1-benzoyl(ethoxycarbonyl)methyl-1-methyl-1,2,3,6-tetrahydropyridinium halides. Chem Heterocycl Comp 43, 1420–1425 (2007). https://doi.org/10.1007/s10593-007-0219-2
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DOI: https://doi.org/10.1007/s10593-007-0219-2