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Rh(III)-Catalyzed Imidoyl C-H Carbamylation and Cyclization to Bicyclic [1,3,5]Triazinones

Danielle N. Confair, Nathaniel S. Greenwood, Brandon Q. Mercado and Jonathan A. Ellman*

*Department of Chemistry, Yale University, New Haven, Connecticut 06520, United States, Email: jonathan.ellmanyale.edu

D. N. Confair, N. S. Greenwood, B. Q. Mercado, J. A. Ellman, Org. Lett., 2020, 22, 8993-8997.

DOI: 10.1021/acs.orglett.0c03393 (free Supporting Information)


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Abstract

Rh(III) catalyzes a synthesis of bicyclic [1,3,5]triazinones from a diverse array of imines with ethyl (pivaloyloxy)carbamate. The preparation of [5,6]- and [6,6]-bicyclic heterocycles substituted with aryl, alkyl, and alkoxy groups demonstrated a broad reaction scope. The development of a three-component variant featuring in situ imine formation is also reported.

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three-component coupling


proposed mechanism



Key Words

fused N-heterocycles


ID: J54-Y2020