Formal (4+2) cycloaddition of azoalkenes with trifluoromethylimidoyl sulfoxonium ylides: synthesis of trifluoromethyl pyridazine derivatives

Abstract

CF₃-substituted imidoyl sulfoxonium ylides (TFISYs) are extraordinarily versatile and powerful synthons for use in cyclization chemistry that affords diverse CF₃-substituted N-heterocycles. We first reacted TFISYs as a two-atom synthon with readily available azoalkenes and then subjected the products to metal-free formal (4+2) cycloaddition chemistry. This protocol features mild conditions and broad substrate scope, is simple to operate, and provides highly functionalized trifluoromethylpyridazines that are widely found in bioactive molecules.