One-Pot Multicomponent Michael and Thorpe–Ziegler Reaction of Aryl Methyl Ketones

Abstract

A regioselective base-promoted Michael and Thorpe–Ziegler reaction between aryl methyl ketones and α,β-unsaturated nitrile was carried out in a single step. Different functional groups in addition to active positions were tolerated under this condition. Results indicated that the reaction proceeds in a consecutive manner as double Michael, triple Michael, and Thorpe–Ziegler condensation. By applying click chemistry, double Michael adducts were converted to bis-tetrazoles, which have broad applications in coordination and medicinal chemistry.