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Synthesis of Furo[2,3-<i>e</i>][1,4]diazepin-3-one Derivatives through Tandem Cyclization/[4 + 3] Annulation Reactions

Bei Zhang, Jinhang Yu, Xin Wu, Zeyu Chai, Guoying Zhao, Zihan Li, Honglan Kang, Xin Lv, Liejin Zhou

2022The Journal of Organic Chemistry18 citationsDOI

Abstract

A variety of furo[2,3-e][1,4]diazepin-3-one derivatives were facilely synthesized through one-pot tandem cyclization/[4 + 3] annulation reactions between enynamides and α-bromohydroxamates. The reactions proceeded efficiently at room temperature, and various functional groups were well tolerated. The obtained furo[2,3-e][1,4]diazepin-3(2H)-ones containing a 7-membered dinitrogen-fused ring might be of biological and medicinal value. The products could be further derived using convenient procedures.

Topics & Concepts

AnnulationTandemChemistryRing (chemistry)Combinatorial chemistryStereochemistryMedicinal chemistryOrganic chemistryCatalysisMaterials scienceComposite materialCatalytic Alkyne ReactionsCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods