Helvetica Chimica Acta p. 1817 - 1822 (1991)
Update date:2022-08-04
Topics:
Schaerer, Daniel
Jindra, Vladimir
Bringhen, Alain O.
Burger, Ulrich
The synthesis of N,N-dimethyl-N-<(pyrrol-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 deg C) with enamines to give pyrrolizine derivatives in acceptable yield (40-50percent).The process is rationalized in terms of an initial Mannich-type reaction which is immediately followed by a cyclization.
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