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Molecules 2013, 18(1), 654-665; doi:10.3390/molecules18010654
Article

Efficient Synthesis of a (Z)-3-Methyleneisoindolin-1-one Library Using Cu(OAc)2•H2O/DBU under Microwave Irradiation

1,* , 2, 2 and 2
1 Instrumental Analysis Center, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China 2 State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institute for Biological Sciences, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China
* Author to whom correspondence should be addressed.
Received: 3 December 2012 / Revised: 21 December 2012 / Accepted: 27 December 2012 / Published: 4 January 2013
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Abstract

Microwave-promoted efficient synthesis of a (Z)-3-methyleneisoindolin-1-one library from 2-bromobenzamides and terminal alkynes using Cu(OAc)2•H2O/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•H2O and DBU without other additives.
Keywords: (Z)-3-methyleneisoindolin-1-one; Cu(OAc)2•H2O/DBU; domino reaction; cross coupling; microwave irradiation (Z)-3-methyleneisoindolin-1-one; Cu(OAc)2•H2O/DBU; domino reaction; cross coupling; microwave irradiation
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Zhang, L.; Zhang, Y.; Wang, X.; Shen, J. Efficient Synthesis of a (Z)-3-Methyleneisoindolin-1-one Library Using Cu(OAc)2•H2O/DBU under Microwave Irradiation. Molecules 2013, 18, 654-665.

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