Abstract

A convenient method for the synthesis of a series of 2-(arylamino)-3H-phenoxazin-3-ones based on the nucleophilic substitution reaction between sterically crowded 3H-phenoxazin-3-one and arylamines performed by short-term heating of the melted reactants at 220–250 °C is described, and the compounds were characterized by means of single-crystal X-ray crystallography, NMR, UV–vis, and IR spectroscopy, as well as cyclic voltammetry. The reaction with o-amino-, o-hydroxy-, and o-mercapto-substituted arylamines widened the scope and provided an access to derivatives of N,O- and N,S-heteropentacyclic quinoxalinophenoxazine, triphenodioxazine and oxazinophenothiazine systems.

Beilstein J. Org. Chem. 2024, 20, 336–345. doi:10.3762/bjoc.20.34

摘要

一种基于空间拥挤的 3 H -phenoxazin-3-one 与芳胺之间的亲核取代反应合成一系列 2-(arylamino)-3 H -phenoxazin-3-ones 的简便方法，通过短期加热进行描述了在 220-250 °C 熔化的反应物，并通过单晶 X 射线晶体学、核磁共振、紫外-可见光和红外光谱以及循环伏安法对化合物进行了表征。与邻氨基、邻羟基和邻巯基取代的芳胺的反应拓宽了范围，并提供了获得N,O-和N,S-杂五环喹喔啉吩恶嗪、三苯二恶嗪和恶嗪吩噻嗪体系衍生物的途径。

贝尔斯坦 J. 组织。化学。 2024, 20, 336–345。doi:10.3762/bjoc.20.34