Ag-Catalyzed Annulation of o-Alkynylaryl Aldehydes, Amines, and Diazo Compounds: Construction of Trifluoromethyl- and Cyano-Functionalized Benzo[d]azepines
Sanoop P. Chandrasekharan, Anamika Dhami and Kishor Mohanan*
*CSIR-Central Drug Research Institute, BS-10/1, Sector 10,
Jankipuram Extension, Sitapur Road, P.O. Box 173, Lucknow 226031, India,
Email: kishor.mohanan
cdri.res.in
S. P. Chandrasekharan, A. Dhami, K. Mohanan, Org. Lett., 2023, 25, 5806-5811.
DOI: 10.1021/acs.orglett.3c02053
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Abstract
A Ag-catalyzed three-component annulation of o-alkynylaryl aldehydes, amines, and trifluorodiazoethane or diazoacetonitrile provides trifluoromethyl- and cyano-functionalized benzo[d]azepines. Key steps in this reaction are the transient formation of an isoquinolinium intermediate and a subsequent ring-expansive addition of in situ-formed silver trifluorodiazoethylide.
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proposed mechanism
Key Words
benzo-fused N-heterocycles, multicomponent reactions
ID: J54-Y2023
