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Updated: Oct 3, 2025

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
3-Trifluoroacetyl-quinolin-2(1H)-ones as Carbonyl and Acid Surrogates in the Passerini-/Ugi-Type Reaction
Desagoni Madhu1,2, Vatsala Rani Jetti2, Banda Narsaiah2
1Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India.
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.
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