Alkylation of Ethyl 2-Aryl-1-hydroxy-4-methyl-1H-imidazole-5-carboxylates with Benzyl Halides

Abstract

The alkylation of ethyl 2-aryl-1-hydroxy-4-methyl-1H-imidazole-5-carboxylates with substituted benzyl halides resulted in the selective formation of O-alkoxy derivatives. N-Alkylation products (1-alkylimidazole 3-oxides) were obtained by the condensation reaction from acyclic starting compounds. In the presence of the 2-hydroxyphenyl substituent in the 2-position of the imidazole ring, selective monoalkylation involving the hydroxyl substituent on the imidazole nitrogen takes place.