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

Hong-Xia Wang; Tian-Qi Wei; Pei Xu; Shun-Yi Wang; Shun-Jun Ji

doi:10.1021/acs.joc.8b02395

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

J Org Chem. 2018 Nov 2;83(21):13491-13497. doi: 10.1021/acs.joc.8b02395. Epub 2018 Oct 19.

Authors

Hong-Xia Wang¹, Tian-Qi Wei², Pei Xu², Shun-Yi Wang², Shun-Jun Ji²

Affiliations

¹ School of Chemistry, Biology and Materials Engineering , Suzhou University of Science and Technology , Suzhou , 215009 , P. R. China.
² Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology , Soochow University , Suzhou , 215123 , P. R. China.

PMID: 30339009
DOI: 10.1021/acs.joc.8b02395

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't