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

Boris V. Lyalin, Vera L. Sigacheva, Anastasia S. Kudinova, Bogdan I. Ugrak, Vladimir A. Petrosyan, Vladimir A. Kokorekin
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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.


Keywords


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

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