A Novel and Chemoselective Process ofN-Alkylation of Aromatic Nitrogen Compounds Using Quaternary Ammonium Salts as Starting Material

Abstract

The process ofN-alkylation of several pyrroles, indoles, and derivative heterocycles is herein described, using quaternary ammonium salts as the source of an alkylating agent. These reactions were carried out on several heterocyclic rings with triethylbenzylammonium chloride or tetradecyltrimethylammonium bromide and an NaOH solution at 50%, leading to a chemoselectiveN-alkylated product and an average yield of 73%. This is an alternative process to the traditional benzylation and methylation ofN-heterocycles with direct handling of alkyl halides.