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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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Publication details

The article was received on 19 Oct 2017, accepted on 10 Nov 2017 and first published on 13 Nov 2017


Article type: Communication
DOI: 10.1039/C7OB02585H
Citation: Org. Biomol. Chem., 2017, Advance Article
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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

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

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