Herein, we report tailored 3-trifluoroacetyl-quinolin-2(1)-ones () as carbonyl and acid surrogates in Passerini- and Ugi-type reactions for the synthesis of α-trifluoromethyl-α-hydroxy carboxamides () and α-trifluoromethyl α-amino acids () in high yields, respectively. The reaction proceeds under mild reaction conditions via an exocyclic carboximidate intermediate (). The amide group in compound acts as an acid component as well as a reversible oxygen nucleophile to facilitate the reaction.
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| http://dx.doi.org/10.1021/acs.joc.1c02107 | DOI Listing |
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