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Abstract <p>A new compound, 5-acetyl-2-amino-4-(2-chloro-5-nitrophenyl)-6-oxo-1-phenyl-1,4,5,6-tetrahydropyridine-3-carbonitrile, was synthesized by the reaction of 2-chloro-5-(nitrobenzylidene)malononitrile with malononitrile and aniline. The product was then subjected to catalytic rearrangement in the presence of ethylenediamine to obtain one more new compound, 4-(2-chloro-5-nitrophenyl)-6-oxo-2-(phenylamino)-1,4,5,6-tetrahydropyridine-3-carbonitrile. The structure of the products was confirmed by NMR spectroscopy and X-ray diffraction analysis. A plausible mechanism of the rearrangement reaction was proposed.</p>

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Catalytic Rearrangement of a Tetrasubstituted Tetrahydropyridine

  • 期刊论文

  • 发表日期：

    2025年5月1日

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  • F. N. Naghiyev,
  • M. R. Komarovskikh,
  • M. V. Tachaev,
  • V. N. Khrustalev,
  • I. G. Mamedov

摘要

Abstract

A new compound, 5-acetyl-2-amino-4-(2-chloro-5-nitrophenyl)-6-oxo-1-phenyl-1,4,5,6-tetrahydropyridine-3-carbonitrile, was synthesized by the reaction of 2-chloro-5-(nitrobenzylidene)malononitrile with malononitrile and aniline. The product was then subjected to catalytic rearrangement in the presence of ethylenediamine to obtain one more new compound, 4-(2-chloro-5-nitrophenyl)-6-oxo-2-(phenylamino)-1,4,5,6-tetrahydropyridine-3-carbonitrile. The structure of the products was confirmed by NMR spectroscopy and X-ray diffraction analysis. A plausible mechanism of the rearrangement reaction was proposed.