Synlett 2013; 24(17): 2233-2240
DOI: 10.1055/s-0033-1339858
letter
© Georg Thieme Verlag Stuttgart · New York

DMAP-Catalyzed Regel-Type Direct C-2 (Hetero)Aroylation of Oxazoles and Thiazoles Derivatives with Acid Chlorides

Pierrik Lassalas
Normandie Université, COBRA, UMR 6014 et FR 3038, Université de Rouen, INSA de Rouen, CNRS, 1 rue Tesnière, 76821 Mont-Saint-Aignan Cedex, France   Fax: +33(235)522962   Email: christophe.hoarau@insa-rouen.fr
,
Francis Marsais
Normandie Université, COBRA, UMR 6014 et FR 3038, Université de Rouen, INSA de Rouen, CNRS, 1 rue Tesnière, 76821 Mont-Saint-Aignan Cedex, France   Fax: +33(235)522962   Email: christophe.hoarau@insa-rouen.fr
,
Christophe Hoarau*
Normandie Université, COBRA, UMR 6014 et FR 3038, Université de Rouen, INSA de Rouen, CNRS, 1 rue Tesnière, 76821 Mont-Saint-Aignan Cedex, France   Fax: +33(235)522962   Email: christophe.hoarau@insa-rouen.fr
› Author Affiliations
Further Information

Publication History

Received: 18 July 2013

Accepted after revision: 27 August 2013

Publication Date:
23 September 2013 (online)


Abstract

A Regel-type transition-metal-free direct C-2 aroylation of (benzo)oxazoles, (benzo)thiazoles and 1,3,4-oxadiazoles with acid chlorides catalyzed by N,N-dimethyl-4-aminopyridine (DMAP) is described. This methodology is effective with several aroyl and heteroaroyl chlorides affording the corresponding 2-keto­azoles in moderate to excellent yields.

Supporting Information

 
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