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Selective S-Arylation of 2-Oxazolidinethiones and N-Arylation of 2-Benzoxazolinones/2-Benzimidazolinones

Abstract

There exist three possible patterns for the reaction of cyclic 2-oxazolidinethione and 2-benzoxazolidinethione with aryne, namely (a) S-arylation, (b) N-arylation, and (c) aryne insertion into thiocarbonyl group (C=S). Our studies demonstrate that S-arylation wins out affording S-aryl dihydrooxazole. In contrast, for related reactions of cyclic 2-benzoxazolinone and 2-benzimidazolinone with aryne, it is found that N-arylation outcompetes O-arylation and aryne insertion into C=O group to give N-aryl 2-benzoxazolinone and N-aryl 2-benzimidazolinone.

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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, Accepted Manuscript
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    Selective S-Arylation of 2-Oxazolidinethiones and 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, Accepted Manuscript , DOI: 10.1039/C7OB00040E

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