Copper(I)-Catalyzed Synthesis of Chlorinated Tetrahydropyridazin-3-ones and 1,2-Diazepan-3-ones from N-Allyl-N′-trichloroacetylhydrazines

The synthesis of chlorinated tetrahydropyridazin-3-ones and 1,2-diazepan-3-ones has been developed. The present paper describes the application of Cu(I)-catalyzed ATRC for the synthesis of heterocyclic molecules containing two heteroatoms (i.e., nitrogen) in the ring for the first time. An easy separation of the individual compounds from the product mixture could be achieved by considering their solubility/insolubility in n-hexane. The presence of three chlorine atoms provides possibilities for further derivatization.