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

[Image: see text] 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. M...

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Autores principales: Cortes Vazquez, Jose, Alharbi, Waad S., Davis, Jacqkis, Moore, Alexia, Nesterov, Vladimir N., Cundari, Thomas R., Wang, Hong, Luo, Weiwei
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9753174/
https://www.ncbi.nlm.nih.gov/pubmed/36530259
http://dx.doi.org/10.1021/acsomega.2c05909
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author Cortes Vazquez, Jose
Alharbi, Waad S.
Davis, Jacqkis
Moore, Alexia
Nesterov, Vladimir N.
Cundari, Thomas R.
Wang, Hong
Luo, Weiwei
author_facet Cortes Vazquez, Jose
Alharbi, Waad S.
Davis, Jacqkis
Moore, Alexia
Nesterov, Vladimir N.
Cundari, Thomas R.
Wang, Hong
Luo, Weiwei
author_sort Cortes Vazquez, Jose
collection PubMed
description [Image: see text] 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.
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spelling pubmed-97531742022-12-16 Three Component Cascade Reaction of Cyclohexanones, Aryl Amines, and Benzoylmethylene Malonates: Cooperative Enamine-Brønsted Acid Approach to Tetrahydroindoles Cortes Vazquez, Jose Alharbi, Waad S. Davis, Jacqkis Moore, Alexia Nesterov, Vladimir N. Cundari, Thomas R. Wang, Hong Luo, Weiwei ACS Omega [Image: see text] 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. American Chemical Society 2022-11-30 /pmc/articles/PMC9753174/ /pubmed/36530259 http://dx.doi.org/10.1021/acsomega.2c05909 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Cortes Vazquez, Jose
Alharbi, Waad S.
Davis, Jacqkis
Moore, Alexia
Nesterov, Vladimir N.
Cundari, Thomas R.
Wang, Hong
Luo, Weiwei
Three Component Cascade Reaction of Cyclohexanones, Aryl Amines, and Benzoylmethylene Malonates: Cooperative Enamine-Brønsted Acid Approach to Tetrahydroindoles
title Three Component Cascade Reaction of Cyclohexanones, Aryl Amines, and Benzoylmethylene Malonates: Cooperative Enamine-Brønsted Acid Approach to Tetrahydroindoles
title_full Three Component Cascade Reaction of Cyclohexanones, Aryl Amines, and Benzoylmethylene Malonates: Cooperative Enamine-Brønsted Acid Approach to Tetrahydroindoles
title_fullStr Three Component Cascade Reaction of Cyclohexanones, Aryl Amines, and Benzoylmethylene Malonates: Cooperative Enamine-Brønsted Acid Approach to Tetrahydroindoles
title_full_unstemmed Three Component Cascade Reaction of Cyclohexanones, Aryl Amines, and Benzoylmethylene Malonates: Cooperative Enamine-Brønsted Acid Approach to Tetrahydroindoles
title_short Three Component Cascade Reaction of Cyclohexanones, Aryl Amines, and Benzoylmethylene Malonates: Cooperative Enamine-Brønsted Acid Approach to Tetrahydroindoles
title_sort three component cascade reaction of cyclohexanones, aryl amines, and benzoylmethylene malonates: cooperative enamine-brønsted acid approach to tetrahydroindoles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9753174/
https://www.ncbi.nlm.nih.gov/pubmed/36530259
http://dx.doi.org/10.1021/acsomega.2c05909
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