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Updated: Sep 19, 2025

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
TBHP/I2 Synergistically Promoted Three-Component Reaction of Isatins, Amines and Methylhetarenes:
Cheng Xu1, Tao Peng1, Minglin Liu1
1Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi 435002, P.R. China.
Abstract:
A TBHP/I2 synergistically promoted three-component reaction of readily available isatins, amines, and methylhetarenes has been established. This transition-metal-free approach provides a concise and practical pathway for the assembly of structurally novel 2-hetarylquinazolin-4(3H)-ones, featuring a wide substrate scope and excellent functional group tolerance. Mechanistic investigations revealed that the TBHP-mediated Baeyer-Villiger-type rearrangement of isatins and the I2-promoted sp3 C-H functionalization of methylhetarenes constituted crucial steps within the reaction sequences. Furthermore, gram-scale synthesis and late-stage modification of the resulting products were successfully implemented.
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