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Abstract <p>A series of previously undescribed 3-(arylamino)-2-(4-arylthiazol-2-yl)acrylonitriles were prepared by the Hantzsch reaction between 3-(arylamino)-2-cyanothioacrylamides and α-bromoketones. Bromination of the prepared 3-(arylamino)-2-(4-arylthiazol-2-yl)acrylonitriles proceeded regioselectively at the C<sup>5</sup> position of, thiazole ring to form previously unknown 3-(arylamino)-2-(4-aryl-5-bromothiazol-2-yl)acrylonitriles in 42–85% yields. Structures of the new compounds were confirmed by 2D NMR (<sup>1</sup>H–<sup>13</sup>C, <sup>1</sup>H–<sup>15</sup>N HSQC, <sup>1</sup>H–<sup>13</sup>C, <sup>1</sup>H–<sup>15</sup>N HMBC) and single crystal X-ray diffraction analysis.</p>

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Synthesis, Structure, and Bromination of 3-(Arylamino)-2-(4-arylthiazol-2-yl)acrylonitriles

  • 期刊论文

  • 发表日期：

    2025年5月21日

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  • N. A. Pakholka,
  • V. V. Dotsenko,
  • A. V. Churakov,
  • and S. G. Krivokolysko

摘要

Abstract

A series of previously undescribed 3-(arylamino)-2-(4-arylthiazol-2-yl)acrylonitriles were prepared by the Hantzsch reaction between 3-(arylamino)-2-cyanothioacrylamides and α-bromoketones. Bromination of the prepared 3-(arylamino)-2-(4-arylthiazol-2-yl)acrylonitriles proceeded regioselectively at the C5 position of, thiazole ring to form previously unknown 3-(arylamino)-2-(4-aryl-5-bromothiazol-2-yl)acrylonitriles in 42–85% yields. Structures of the new compounds were confirmed by 2D NMR (1H–13C, 1H–15N HSQC, 1H–13C, 1H–15N HMBC) and single crystal X-ray diffraction analysis.