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Issue 46, 2017
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Copper-catalyzed highly selective synthesis of 2-benzyl- and 2-benzylidene-substituted benzo[b]thiazinones from 2-iodophenylcinnamamides and potassium sulfide

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Abstract

An efficient and practical procedure for the synthesis of 2-benzyl- and 2-benzylidene-substituted benzo[b]thiazinones from easily available 2-iodophenylcinnamamides and potassium sulfide has been developed. In the presence of DBU, the reaction proceeds via electrophilic addition, followed by dehydrogenation and reduction to give 2-benzyl benzo[b]thiazinones. Furthermore, 2-benzylidenebenzo[b]thiazinones were obtained in moderate to good yields without the addition of DBU.

Graphical abstract: Copper-catalyzed highly selective synthesis of 2-benzyl- and 2-benzylidene-substituted benzo[b]thiazinones from 2-iodophenylcinnamamides and potassium sulfide

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Article information


Submitted
19 Oct 2017
Accepted
10 Nov 2017
First published
13 Nov 2017

Org. Biomol. Chem., 2017,15, 9804-9808
Article type
Communication

Copper-catalyzed highly selective synthesis of 2-benzyl- and 2-benzylidene-substituted benzo[b]thiazinones from 2-iodophenylcinnamamides and potassium sulfide

W. Liu, H. Min, X. Zhu, G. Deng and Y. Liang, Org. Biomol. Chem., 2017, 15, 9804
DOI: 10.1039/C7OB02585H

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