Organic chemistry

Combinatorial chemistry

Cycloisomerization

Palladium

Sonogashira coupling

Amine gas treating

One-pot synthesis

Catalysis

Chemistry

Trifluoromethyl

Acylation

Propargyl

Alkyl

Aryl

Synfacts

Reported is a concise one-pot three-step amidation, Pd-catalyzed acylation, and cycloisomerization procedure for the synthesis of 1-(hetero)aryl-2-[2-(hetero)aryloxazol-5-yl] ethanones from propargyl amine and acid chlorides in moderate to good overall yields. Anhydrides may be used as replacements of acid chlorides in the first step allowing access to 2-trifluoromethyl derivatives; carbonylative Sonogashira coupling can be used equally well in the second step. The structures have been confirmed by X-ray crystal structure analysis of one of the products.

One-Pot Synthesis of 2,5-Disubstituted Oxazoles