112969-91-2Relevant articles and documents
DMAP-catalyzed regel-type direct C-2 (Hetero)aroylation of oxazoles and thiazoles derivatives with acid chlorides
Lassalas, Pierrik,Marsais, Francis,Hoarau, Christophe
, p. 2233 - 2240 (2013)
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 het
Synthesis of (Trimethylsilyl)thiazoles and Reactions with Carbonyl Compounds. Selectivity Aspects and Synthetic Utility
Dondoni, Alessandro,Fantin, Giancarlo,Fogagnolo, Marco,Medici, Alessandro,Pedrini, Paola
, p. 1748 - 1761 (2007/10/02)
Synthetic routes to all possible regioisomeric mono- and bis(trimethylsilyl)thiazoles as well as to the tris(trimethylsilyl) derivative via lithiation-silylation sequences of the thiazole ring followed by selective protodesilylation in some cases are described. (Trimethylsilyl)thiazoles serve as thiazolyl donor synthons upon reaction with carbonyl compounds (ketenes, acyl chlorides, aldehydes) for the preparation of mono- and bis-substituted thiazoles in very good yields.Carbodesilylation occurs more readily at the 2- than 5-position, whereas no reaction takes place at the 4-position.A mechanism via a thiazolium 2-ylide as an intermediate is suggested for the carbodesilylation at the 2-position.