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Abstract <p>The reaction of ethyl 3-aryl-2-cyanoacrylates (arylmethylene cyanoacetates) with <i>N</i><sup>1</sup>,<i>N</i><sup>3</sup>-disubstituted malonamides in the presence of Et<sub>3</sub>N under mild conditions (absolute EtOH, 25°C) produces new stable Michael adducts, ethyl 3-aryl-2-cyano-5-oxo-5-(<i>N</i>-R-amino)-4-(<i>N</i>-R-carbamoyl)pentanoates, in 57–95% yields. The structure of the obtained compounds was confirmed by IR, <sup>1</sup>H, <sup>13</sup>C NMR spectroscopy, high-resolution mass spectrometry, and X-ray crystallography. The stereochemical features of the obtained Michael adducts have been studied. Calculations using the semi-empirical GFN2-xTB method showed that the cyclization of the obtained adducts is a thermodynamically favorable process but has a high energy barrier (~206 kJ/mol) and cannot occur under the reaction conditions. The antibacterial activity of a series of the obtained Michael adducts was studied.</p>

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Reaction of Ethyl 3-Aryl-2-cyanoacrylates with N,N-Disubstituted Malonamides: Synthesis and Properties of Stable Michael Adducts

  • 期刊论文

  • 发表日期：

    2025年11月1日

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  • Anush Kh. Khachatryan,
  • Anush A. Sargsyan,
  • Katya A. Avagyan,
  • Anahit G. Simonyan,
  • Angin N. Zograbyan,
  • Alik E. Badasyan,
  • Anna V. Gevorgyan,
  • Hrachya M. Stepanyan,
  • Alexander V. Bespalov,
  • Victor V. Dotsenko

摘要

Abstract

The reaction of ethyl 3-aryl-2-cyanoacrylates (arylmethylene cyanoacetates) with N1,N3-disubstituted malonamides in the presence of Et3N under mild conditions (absolute EtOH, 25°C) produces new stable Michael adducts, ethyl 3-aryl-2-cyano-5-oxo-5-(N-R-amino)-4-(N-R-carbamoyl)pentanoates, in 57–95% yields. The structure of the obtained compounds was confirmed by IR, 1H, 13C NMR spectroscopy, high-resolution mass spectrometry, and X-ray crystallography. The stereochemical features of the obtained Michael adducts have been studied. Calculations using the semi-empirical GFN2-xTB method showed that the cyclization of the obtained adducts is a thermodynamically favorable process but has a high energy barrier (~206 kJ/mol) and cannot occur under the reaction conditions. The antibacterial activity of a series of the obtained Michael adducts was studied.