A simple method for the synthesis of diarylamines containing a nitroso group in the ortho position based on the SNH arylamination of 5-nitroisoquinoline

Abstract

A simple and efficient arylamination reaction of 5-nitroisoquinoline based on the oxidative nucleophilic substitution of hydrogen was demonstrated under metal-catalyst-free conditions. This reaction can be used as a method for the synthesis of isoquinoline-based diarylamines containing a nitroso group in the ortho position, which are compounds with high synthetic potential. The oxidation of the latter leads to the formation of 6-arylamino-5-nitroisoquinoline N-oxides. The absence of the need to introduce leaving groups and a good overall yield are features of this reaction.