Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance upgrade on Thursday 4th of May 2017 from 8.00am to 9.00am (BST).

During this time our websites will be offline temporarily. If you have any questions please use the feedback button on this page. We apologise for any inconvenience this might cause and thank you for your patience.



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

Author affiliations

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

Back to tab navigation
Please wait while Download options loads

Supplementary files

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, Advance Article
  •   Request permissions

    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, Advance Article , DOI: 10.1039/C7OB00040E

Search articles by author