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Scientific article
English

Reaction of the 5-Azoniafulvene Ion with Enamines: A New Approach to Pyrrolizines

Published inHelvetica Chimica Acta, vol. 74, no. 8, p. 1817-1822
Publication date1991
Abstract

The synthesis of N,N-dimethyl-N-[(pyrro-1-yl)methyl]anilinium chloride (14) and of the corresponding p-toluidinium salt 15 is described. These salts, when dissolved in polar solvents, are shown to be in equilibrium with 1-(chloromethyl)pyrrole (17) and thereby potentially with the 5-azoniafulvene ion (2). Consequently, they react under very mild conditions (MeCN, 60°) with enamines to give pyrrolizine derivatives in acceptable yield (40–50°). The process is rationalized in terms of an initial Mannich-type reaction which is immediately followed by acyclization.

Funding
  • Swiss National Science Foundation - 20-27665.89
Citation (ISO format)
SCHARER, Daniel et al. Reaction of the 5-Azoniafulvene Ion with Enamines: A New Approach to Pyrrolizines. In: Helvetica Chimica Acta, 1991, vol. 74, n° 8, p. 1817–1822. doi: 10.1002/hlca.19910740824
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ISSN of the journal0018-019X
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