I2/TBHP-Mediated Oxidative Coupling of Amino-Based Bisnucleophiles and Isocyanides: Access to 2‑Aminobenzoxazinones, 2‑Aminobenzoxazines, and 2‑Aminoquinazolines under Metal-Free Conditions

An I2/tert-butyl hydroperoxide (TBHP)-mediated oxidative coupling reaction of isocyanides with amino-based bisnucleophiles is described for the synthesis of 2-aminobenzoxazinones, 2-aminobenzoxazines, and 2-aminoquinozolines in moderate to excellent yields. Furthermore, this method provides a simple...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-11, Vol.83 (21), p.13491-13497
Main Authors: Wang, Hong-Xia, Wei, Tian-Qi, Xu, Pei, Wang, Shun-Yi, Ji, Shun-Jun
Format: Article
Language:English
Online Access:Get full text
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Summary:An I2/tert-butyl hydroperoxide (TBHP)-mediated oxidative coupling reaction of isocyanides with amino-based bisnucleophiles is described for the synthesis of 2-aminobenzoxazinones, 2-aminobenzoxazines, and 2-aminoquinozolines in moderate to excellent yields. Furthermore, this method provides a simple and practical method to construct potential functionalized biologically active molecules.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b02395