Synthesis of N-Unsubstituted α-Alkylated Pyrrol-2-Acetonitriles

Abstract

Nucleophilic addition of alkyllithium compounds to in situ generated 6-dimethyl-amino-1-azafulvene produced the α-alkylated pyrrole Mannich bases (3). Reaction of the p-toluenesulfonic acid salt of such bases with excess sodium cyanide in wet acetonit-rile. at reflux temperature, provided the corresponding α-alkylpyrrol-2-acetonitriles (5) via the putative 6-alkyl-1-azafulvenes (4).