Efficient Synthesis of a (Z)-3-Methyleneisoindolin-1-one Library Using Cu(OAc)(2)•H(2)O/DBU under Microwave Irradiation

Microwave-promoted efficient synthesis of a (Z)-3-methyleneisoindolin-1-one library from 2-bromobenzamides and terminal alkynes using Cu(OAc)(2)•H(2)O/DBU is described. Various benzamide substituents, ring substitutions, including heteroaryl, aryl acetylenes and aliphatic alkynes, could be applied t...

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Detalles Bibliográficos
Autores principales: Zhang, Li, Zhang, Yongliang, Wang, Xin, Shen, Jingkang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2013
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6269936/
https://www.ncbi.nlm.nih.gov/pubmed/23292328
http://dx.doi.org/10.3390/molecules18010654
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author Zhang, Li
Zhang, Yongliang
Wang, Xin
Shen, Jingkang
author_facet Zhang, Li
Zhang, Yongliang
Wang, Xin
Shen, Jingkang
author_sort Zhang, Li
collection PubMed
description Microwave-promoted efficient synthesis of a (Z)-3-methyleneisoindolin-1-one library from 2-bromobenzamides and terminal alkynes using Cu(OAc)(2)•H(2)O/DBU is described. Various benzamide substituents, ring substitutions, including heteroaryl, aryl acetylenes and aliphatic alkynes, could be applied to afford the desired products in good to moderate yield with high stereoselectivity. It is noteworthy that DBU maybe play a dual role as not only the base, but also as a ligand for copper. The reaction is catalyzed by the complex of Cu(OAc)(2)•H(2)O and DBU without other additives.
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spelling pubmed-62699362018-12-14 Efficient Synthesis of a (Z)-3-Methyleneisoindolin-1-one Library Using Cu(OAc)(2)•H(2)O/DBU under Microwave Irradiation Zhang, Li Zhang, Yongliang Wang, Xin Shen, Jingkang Molecules Article Microwave-promoted efficient synthesis of a (Z)-3-methyleneisoindolin-1-one library from 2-bromobenzamides and terminal alkynes using Cu(OAc)(2)•H(2)O/DBU is described. Various benzamide substituents, ring substitutions, including heteroaryl, aryl acetylenes and aliphatic alkynes, could be applied to afford the desired products in good to moderate yield with high stereoselectivity. It is noteworthy that DBU maybe play a dual role as not only the base, but also as a ligand for copper. The reaction is catalyzed by the complex of Cu(OAc)(2)•H(2)O and DBU without other additives. MDPI 2013-01-04 /pmc/articles/PMC6269936/ /pubmed/23292328 http://dx.doi.org/10.3390/molecules18010654 Text en © 2013 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Zhang, Li
Zhang, Yongliang
Wang, Xin
Shen, Jingkang
Efficient Synthesis of a (Z)-3-Methyleneisoindolin-1-one Library Using Cu(OAc)(2)•H(2)O/DBU under Microwave Irradiation
title Efficient Synthesis of a (Z)-3-Methyleneisoindolin-1-one Library Using Cu(OAc)(2)•H(2)O/DBU under Microwave Irradiation
title_full Efficient Synthesis of a (Z)-3-Methyleneisoindolin-1-one Library Using Cu(OAc)(2)•H(2)O/DBU under Microwave Irradiation
title_fullStr Efficient Synthesis of a (Z)-3-Methyleneisoindolin-1-one Library Using Cu(OAc)(2)•H(2)O/DBU under Microwave Irradiation
title_full_unstemmed Efficient Synthesis of a (Z)-3-Methyleneisoindolin-1-one Library Using Cu(OAc)(2)•H(2)O/DBU under Microwave Irradiation
title_short Efficient Synthesis of a (Z)-3-Methyleneisoindolin-1-one Library Using Cu(OAc)(2)•H(2)O/DBU under Microwave Irradiation
title_sort efficient synthesis of a (z)-3-methyleneisoindolin-1-one library using cu(oac)(2)•h(2)o/dbu under microwave irradiation
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6269936/
https://www.ncbi.nlm.nih.gov/pubmed/23292328
http://dx.doi.org/10.3390/molecules18010654
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