135541-06-9Relevant academic research and scientific papers
176. Reaction of the 5-Azoniafulvene Ion with Enamines: A New Approach to Pyrrolizines
Schaerer, Daniel,Jindra, Vladimir,Bringhen, Alain O.,Burger, Ulrich
, p. 1817 - 1822 (2007/10/02)
The synthesis of N,N-dimethyl-N-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.
