Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 5, Pages 2301-2314Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02107
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In this study, tailored 3-trifluoroacetyl-quinolin-2(1H)-ones were used as carbonyl and acid surrogates in Passerini- and Ugi-type reactions to synthesize alpha-trifluoromethyl-alpha-hydroxy carboxamides and alpha-trifluoromethyl alpha-amino acids, achieving high yields under mild reaction conditions via an exocyclic carboximidate intermediate. The amide group in compound 1 acted as both an acid component and a reversible oxygen nucleophile to facilitate the reaction.
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 alpha-trifluoromethyl-alpha-hydroxy carboxamides (4) and alpha-trifluoromethyl alpha-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.
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