ELECTROOXIDATIVE N‒N CROSS COUPLING: A WAY TO NEW AZOPYRAZOLES

Authors

  • Boris V. Lyalin N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Vera L. Sigacheva N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Anastasia S. Kudinova N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Bogdan I. Ugrak N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Vladimir A. Petrosyan N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Vladimir A. Kokorekin N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia I. M. Sechenov First Moscow State Medical University (Sechenov University), 8 Build. 2 Trubetskaya St., Moscow 119991, Russia All-Russian Research Institute of Phytopathology, 5 Institute St., Bol'shiye Vyazemy, Moscow Region 143050, Russia

DOI:

https://doi.org/10.1007/6424

Keywords:

aminopyrazoles, azopyrazoles, bromine, hypohalites, nickel oxide hydroxide, electrooxidation, N–N cross coupling.

Abstract

In this article, we showed N‒N cross coupling of 4-(un)substituted 1-alkyl-3-aminopyrazoles using electrogenerated reagents (NiO(OH), NaOCl, NaOBr, or Br2) for the first time. It was found that the oxidation potentials of the initial azoles reflect their reactivity and are the key factors in the efficiency of the target and side processes. This made it possible to identify suitable combinations of azoles and electrogenerated reagents and to obtain unsymmetrical azo compounds under mild conditions in aqueous media with 48‒83% yields.

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Published

2022-01-27

Issue

Vol. 58 No. 1 (2022)

Section

Original Papers