A Convenient Method for Preparations of 1-Acylimidazoles and Carboxamides by Using Novel Imidazolylsilane Derivatives

Abstract Various imidazolylsilane derivatives were synthesized by a trans-silylation procedure between 1-(trimethylsilyl)imidazoles and chlorosilanes. Among them, tris- and tetrakis(imidazol-1-yl)silane compounds reacted smoothly with free carboxylic acids to form the corresponding 1-acylimidazoles, which subsequently underwent condensation with amines to afford carboxamides in good to high yields. These results indicate that novel reagents containing silicon–imidazole linkage are effectively utilized as dehydrating reagents to form carboxylic acid derivatives from free carboxylic acids and nucleophiles under mild conditions.