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.