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

Danielle N. Confair | Zendy; Nathaniel S. Greenwood | Zendy; Brandon Q. Mercado | Zendy; Jonathan A. Ellman | Zendy

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Rh(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.

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