Desagoni Madhu, V. Jetti, B. Narsaiah
Feb 14, 2022
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Journal
The Journal of organic chemistry
Abstract
Herein, we report tailored 3-trifluoroacetyl-quinolin-2(1H)-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.