α-Keto Acids as Triggers and Partners for the Synthesis of Quinazolinones, Quinoxalinones, Benzooxazinones, and Benzothiazoles in Water
Jian Huang, Wei Chen, Jiazhi Liang, Qin Yang, Yan Fan, Mu‐Wang Chen, Yiyuan Peng
Abstract
A general and efficient method for the synthesis of quinazolinones, quinoxalinones, benzooxazinones, and benzothiazoles from the reactions of α-keto acids with 2-aminobenzamides, benzene-1,2-diamines, 2-aminophenols, and 2-aminobenzenethiols, respectively, is described. The reactions were conducted under catalyst-free conditions, using water as the sole solvent with no additive required, and successfully applied to the synthesis of sildenafil. More importantly, these reactions can be conducted on a mass scale, and the products can be easily purified through filtration and washing with ethanol (or crystallized).
Topics & Concepts
CatalysisSolventChemistryEthanolCombinatorial chemistryOrganic chemistryFiltration (mathematics)BenzeneMathematicsStatisticsQuinazolinone synthesis and applicationsSynthesis and Biological EvaluationPhenothiazines and Benzothiazines Synthesis and Activities