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<p>Tendencies for reactions of aminopyridines with NaOCl generated electrochemically both in aqueous solution and in the heterophase H<sub>2</sub>O—Bu<sup>t</sup>OH system were estimated for the first time. Aminopyridines readily soluble under conditions of single-step process reacted with NaOCl in aqueous solution to give azodipyridines in high yields (up to 83%). The reaction efficiency depended on the position of NH<sub>2</sub> group at the pyridine ring and decreased upon going from 3- to 2- and 4-aminopyridines. A two-step synthesis of azodipyridines in the yield of up to 85% was proposed for aminopyridines poorly soluble in water, which was carried out under mild conditions in the H<sub>2</sub>O—Bu<sup>t</sup>OH system. It was also found that the reaction of 2-aminopyridine with either NaOBr or NiO(OH) generated electrochemically does not give azodipyridines.</p>

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Oxidative N—N-coupling of aminopyridines with electrochemically generated NaOCl as the convenient method for the synthesis of substituted azodipyridines

  • 期刊论文

  • 发表日期：

    2025年4月1日

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  • V. L. Sigacheva,
  • B. V. Lyalin

摘要

Tendencies for reactions of aminopyridines with NaOCl generated electrochemically both in aqueous solution and in the heterophase H2O—ButOH system were estimated for the first time. Aminopyridines readily soluble under conditions of single-step process reacted with NaOCl in aqueous solution to give azodipyridines in high yields (up to 83%). The reaction efficiency depended on the position of NH2 group at the pyridine ring and decreased upon going from 3- to 2- and 4-aminopyridines. A two-step synthesis of azodipyridines in the yield of up to 85% was proposed for aminopyridines poorly soluble in water, which was carried out under mild conditions in the H2O—ButOH system. It was also found that the reaction of 2-aminopyridine with either NaOBr or NiO(OH) generated electrochemically does not give azodipyridines.