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Updated: Sep 11, 2025

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Synthesis of 4-(arylthio)isoquinolin-1(2H)-ones via TBHP-mediated sequential amidation/thioetherification of
Chuanquan Chu1, Jinhui Peng1, Lijuan Jin1
1Department of Food and Chemical Engineering, Shaoyang University, Shaoyang, 422100, China. syudhwang@163.com.
Abstract:
Here, a simple, efficient, and practical method for the assembly of 4-(arylthio)isoquinolin-1(2H)-ones via TBHP-mediated 1,4-difunctionalization of N-alkylisoquinolinium iodide salts under metal-free conditions is reported. This strategy features readily available starting materials, operational simplicity, and metal-free conditions. Remarkably, a variety of (hetero)aryl/alkyl thiols, diphenyl disulfide, diphenyl diselenide, and N-alkylisoquinolinium bromides or chlorides are compatible with this method, which generates the desired 4-(arylthio)isoquinolin-1(2H)-ones in 30-92% yields. The potential synthetic utility is demonstrated by its gram-scale synthesis and derivatizations. The mechanistic experiments indicate that the iodide plays a key role in this transformation.
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