A versatile way for the synthesis of monomethylamines by reduction of N-substituted carbonylimidazoles with the NaBH4/I2 system

Abstract

An economical and versatile protocol for the one-pot synthesis of monomethylamines by reduction of N-substituted carbonylimidazoles with NaBH4/I2 in THF at reflux temperature is described. This method used no special catalyst and various monomethylamines can be easily obtained in moderate to good yields from a wide range of raw materials including amines (primary amines and secondary amines), carboxylic acids and isocyanates. Besides, an interesting reduction selectivity was observed. Exploration of the reaction process shows that it undergoes a two-step pathway via a formamide intermediate and the reduction of the formamide intermediate to monomethylamine as the rate-determining step. This work can contribute significantly expanding the applications of N-substituted carbonylimidazoles.

Keywords

• amines
• carboxylic acids
• isocyanates
• monomethylamines
• n-substituted carbonylimidazoles
• reduction