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Three Component Cascade Reaction of Cyclohexanones, Aryl Amines, and Benzoylmethylene Malonates: Cooperative Enamine-Bronsted Acid Approach to Tetrahydroindoles.

ABSTRACT: A three-component cascade reaction comprising cyclic ketones, arylamines, and benzoylmethylene malonates has been developed to access 4,5,6,7-tetrahydro-1H-indoles. The reaction was achieved through cooperative enamine-Brønsted catalysis in high yields with wide substrate scopes. Mechanistic studies identified the role of the Brønsted acid catalyst and revealed the formation of an imine intermediate, which was confirmed by X-ray crystallography.

SUBMITTER: Cortes Vazquez J

PROVIDER: S-EPMC9753174 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature

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Three Component Cascade Reaction of Cyclohexanones, Aryl Amines, and Benzoylmethylene Malonates: Cooperative Enamine-Brønsted Acid Approach to Tetrahydroindoles.

Cortes Vazquez Jose J Alharbi Waad S WS Davis Jacqkis J Moore Alexia A Nesterov Vladimir N VN Cundari Thomas R TR Wang Hong H Luo Weiwei W

ACS omega 20221130 49

A three-component cascade reaction comprising cyclic ketones, arylamines, and benzoylmethylene malonates has been developed to access 4,5,6,7-tetrahydro-1H-indoles. The reaction was achieved through cooperative enamine-Brønsted catalysis in high yields with wide substrate scopes. Mechanistic studies identified the role of the Brønsted acid catalyst and revealed the formation of an imine intermediate, which was confirmed by X-ray crystallography. ...[more]

PMID: 36530259

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