3-Trifluoroacetyl-quinolin-2(1 H )-ones as Carbonyl and Acid Surrogates in the Passerini-/Ugi-Type Reaction.

Herein, we report tailored 3-trifluoroacetyl-quinolin-2(1 H )-ones ( 1 ) as carbonyl and acid surrogates in Passerini- and Ugi-type reactions for the synthesis of α-trifluoromethyl-α-hydroxy carboxamides ( 4 ) and α-trifluoromethyl α-amino acids ( 6 ) in high yields, respectively. The reaction proceeds under mild reaction conditions via an exocyclic carboximidate intermediate ( 3 ). The amide group in compound 1 acts as an acid component as well as a reversible oxygen nucleophile to facilitate the reaction.