Open AccessRh(III)-Catalyzed Imidoyl C–H Carbamylation and Cyclization to Bicyclic [1,3,5]Triazinones
Author(s) -
Danielle N. Confair,
Nathaniel S. Greenwood,
Brandon Q. Mercado,
Jonathan A. Ellman
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c03393
Subject(s) - bicyclic molecule , chemistry , catalysis , alkyl , imine , aryl , carbamate , alkoxy group , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry
A Rh(III)-catalyzed synthesis of bicyclic [1,3,5]triazinones from a diverse array of imines coupled with ethyl (pivaloyloxy)carbamate is reported. The preparation of [5,6]- and [6,6]-bicyclic heterocycles substituted with aryl, alkyl, and alkoxy groups demonstrated a broad reaction scope. The efficiency of this approach was further enhanced with the development of a three-component variant featuring in situ imine formation. X-ray crystallographic characterization of a rhodacycle formed by imidoyl C-H activation provides support for the proposed mechanism.