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

Pierrik Lassalas, Francis Marsais, 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, Email: christophe.hoarauinsa-rouen.fr

P. Lassalas, F. Marsais, C. Hoarau, Synlett, 2013, 24, 2233-2240.

DOI: 10.1055/s-0033-1339858 (free Supporting Information)


Abstract

A Regel-type transition-metal-free direct C-2 aroylation of (benzo)oxazoles, (benzo)thiazoles and 1,3,4-oxadiazoles with acid chlorides is catalyzed by N,N-dimethyl-4-aminopyridine (DMAP) and affords the corresponding 2-keto­azoles in good yields.

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Key Words

acylation, azoles (oxazoles, benzoxazoles, thiazoles, benzothiazoles), C-H functionalization, heterocycles, metal-free, regioselectivity


ID: J60-Y2013