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[4+3]-Cycloaddition Reaction of Sulfilimines with Cyclobutenones: Access to Benzazepinones

Xiaozhou Xie, Jiangtao Sun

2021Organic Letters31 citationsDOI

Abstract

A catalyst-free [4+3]-cycloaddition reaction of N-aryl sulfilimines with cyclobutenones is described, which provides a straightforward protocol for synthesizing 1,5-dihydro-2H-benzo[b]azepin-2-ones under mild reaction conditions. This reaction features a broad substrate scope and good functional group tolerance and does not require catalysts or additives. Moreover, using N-pyridinyl sulfilimine as the substrate, a series of pyridoazepinones have also been prepared.

Topics & Concepts

CycloadditionChemistryCatalysisSubstrate (aquarium)ArylReaction conditionsFunctional groupCombinatorial chemistryScope (computer science)Medicinal chemistryOrganic chemistryComputer scienceProgramming languageAlkylPolymerGeologyOceanographySynthesis and Catalytic ReactionsCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods