tert-Butyl Hydroperoxide Promoted the Reaction of Quinazoline-3-oxides with Primary Amines Affording Quinazolin-4(3<i>H</i>)-ones
Jin Luo, Juelin Wan, Lianlian Wu, Lingyun Yang, Tao Wang
Abstract
An efficient and facile approach for the synthesis of quinazolin-4(3H)-ones via the reaction of quinazoline-3-oxides with primary amines is described. This approach is demonstrated to be applicable for a broad range of substrates and proceeds efficiently under metal-free and mild reaction conditions employing easily available tert-butyl hydroperoxide as the oxidant. Remarkably, 3-(2-(1H-indol-3-yl) ethyl)quinazolin-4(3H)-one 3w, which was conveniently obtained by this process in 70% yield, was an excellent precursor for the synthesis of bioactive evodiamine and rutaempine.
Topics & Concepts
ChemistryQuinazolinePrimary (astronomy)Yield (engineering)EvodiamineCombinatorial chemistryReaction conditionsOrganic chemistryCatalysisMetallurgyChromatographyAstronomyMaterials sciencePhysicsQuinazolinone synthesis and applicationsSynthesis and Biological EvaluationPhenothiazines and Benzothiazines Synthesis and Activities