A SIMPLE METHOD FOR THE SYNTHESIS OF DIARYLAMINES CONTAINING A NITROSO GROUP IN THE ORTHO POSITION BASED ON THE S<sub>N</sub><sup>H</sup> ARYLAMINATION OF 5-NITROISOQUINOLINE

Authors

  • Diana Y. Pobedinskaya Department of Chemistry, North Caucasus Federal University, 1 Pushkin St., Stavropol 355017
  • Oleg P. Demidov Department of Chemistry, North Caucasus Federal University, 1 Pushkin St., Stavropol 355017
  • Elena K. Avakyan Department of Chemistry, North Caucasus Federal University, 1 Pushkin St., Stavropol 355017
  • Anastasia A. Borovleva Department of Chemistry, North Caucasus Federal University, 1 Pushkin St., Stavropol 355017
  • Alexander N. Larin Department of Chemistry, North Caucasus Federal University, 1 Pushkin St., Stavropol 355017
  • Artem P. Ermolenko Department of Chemistry, North Caucasus Federal University, 1 Pushkin St., Stavropol 355017
  • Ivan V. Borovlev Department of Chemistry, North Caucasus Federal University, 1 Pushkin St., Stavropol 355017

Keywords:

heterocycles, nitroso compound, metal-free C–N bond formation, oxidative SNH arylamination, redox process, SNH methodology

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.

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Published

2024-05-28

Issue

Vol. 60 No. 3/4 (2024)

Section

Original Papers