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

ABSTRACT: 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.

SUBMITTER: Confair DN

PROVIDER: S-EPMC7702018 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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

Confair Danielle N DN Greenwood Nathaniel S NS Mercado Brandon Q BQ Ellman Jonathan A JA

Organic letters 20201110 22

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 imidoy ...[more]

PMID: 33172274

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