105243-91-2Relevant articles and documents
Formation of the 5-Azoniafulvene Ion and its Benzo-annellated Analogue from N-Mannich Bases of Pyrrole and Indole
Burger, Ulrich,Bringhen, Alain O.,Wirthner, Philippe J.,Schaerer, Jean-Claude
, p. 2275 - 2281 (1985)
1-Dialkylaminomethylpyrroles are shown to behave in many respects like aminals.Acylation by an acid chloride, for instance, occurs normally at the amine-type N-atom rather than at the pyrrol ring.Spontaneous cleavage of the resulting quaternary acylammoni
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.