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Issue 19, 2017
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Selective S-arylation of 2-oxazolidinethiones and selective N-arylation of 2-benzoxazolinones/2-benzimidazolinones

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Abstract

There exist three possible patterns for the reaction of cyclic 2-oxazolidinethione and 2-benzoxazolidinethione with arynes, namely (a) S-arylation, (b) N-arylation, and (c) aryne insertion into the thiocarbonyl group (C[double bond, length as m-dash]S). Our studies demonstrate that S-arylation wins out affording S-aryl dihydrooxazoles. In contrast, for related reactions of cyclic 2-benzoxazolinone and 2-benzimidazolinone with arynes, it is found that N-arylation outcompetes O-arylation and aryne insertion into the C[double bond, length as m-dash]O group to give N-aryl 2-benzoxazolinones and N-aryl 2-benzimidazolinones.

Graphical abstract: Selective S-arylation of 2-oxazolidinethiones and selective N-arylation of 2-benzoxazolinones/2-benzimidazolinones

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Publication details

The article was received on 06 Jan 2017, accepted on 11 Apr 2017 and first published on 12 Apr 2017


Article type: Communication
DOI: 10.1039/C7OB00040E
Citation: Org. Biomol. Chem., 2017,15, 4058-4063
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    Selective S-arylation of 2-oxazolidinethiones and selective N-arylation of 2-benzoxazolinones/2-benzimidazolinones

    C. Sun, Y. Lu, Q. Zhang, R. Lu, L. Bao, M. Shen and H. Xu, Org. Biomol. Chem., 2017, 15, 4058
    DOI: 10.1039/C7OB00040E

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