Reactions of Substituted Oxazoles
and Thiazoles with Acid Chlorides: Carbon-Carbon
Bond Formation through Cyclic Ketene Acetals

Sabornie Chatterjee; Guozhong Ye; Yingquan Song; Bobby Lloyd Barker; Charles U. Pittman

doi:10.1055/s-0030-1258224

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Synthesis 2010(19): 3384-3394
DOI: 10.1055/s-0030-1258224

PAPER

Reactions of Substituted Oxazoles and Thiazoles with Acid Chlorides: Carbon-Carbon Bond Formation through Cyclic Ketene Acetals

Sabornie Chatterjee, Guozhong Ye, Yingquan Song, Bobby Lloyd Barker, Jr. Charles U. Pittman*
Department of Chemistry, Mississippi State University, Mississippi State, MS 39762, USA
Fax: +1(662)3257611; e-Mail: cpittman@chemistry.msstate.edu;

Further Information

Publication History

Received 3 April 2010
Publication Date:
20 August 2010 (online)

Abstract
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Abstract

Reactions of 2,4,5-trimethyloxazole, 2,4,5-trimethylthiazole, 2-methylthiazole, and 2-ethyl-4,5-dimethylthiazole with different acid chlorides in the presence of different bases were explored. Arylvinyl esters of substituted benzoic acids containing substituted oxazoles or thiazoles were formed when aroyl chlorides were used. Degrees of aroylation were different with different bases. Reactions with alkyl acid chlorides were also explored. Most of these reactions occurred through cyclic ketene acetal intermediates.

Key words

carbon-carbon bond formation - oxazoles - thiazoles - vinyl esters - in situ generated cyclic ketene acetal

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CCDC 765577 (3d), 765578 (4d), and 765826 (9a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.