Synthesis of 1,4-diazepinone derivatives <i>via</i> a domino aza-Michael/S<sub>N</sub>2 cyclization of 1-azadienes with α-halogenoacetamides
Chunhao Yuan, Hui Zhang, Mengna Yuan, Lei Xie, Xiaoqun Cao
Abstract
A novel cyclization of α-halogenoacetamides with 1-azadienes has been developed for the efficient preparation of monocyclic 1,4-diazepinones in one step under transition metal-free conditions. Various α-halogenoacetamides and 1-azadienes are well tolerated and give the desired products in good to excellent yields. This cyclization also demonstrates potential synthetic utility on a gram-scale and further transformation.
Topics & Concepts
DominoChemistryMichael reactionCombinatorial chemistryTransformation (genetics)StereochemistryOrganic chemistryCatalysisBiochemistryGeneSynthesis and Biological EvaluationCatalytic C–H Functionalization MethodsSynthesis of heterocyclic compounds