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Abstract <p>A series of new <i>N</i>-aryl-2-[(1-aryl-7,8-dimethoxy-5<i>H</i>-2,3-benzodiazepin-4-yl)sulfanyl]acetamides were synthesized by the S-alkylation of 1-aryl-7,8-dimethoxy-3,5-dihydro-4<i>H</i>-2,3-benzodiazepine-4-thiones with <i>N</i>-aryl-2-chloroacetamides. The reaction of 2,3-benzodiazepine-4-thiones with chloroacetic acid in the presence of bases afforded the corresponding 1-aryl-7,8-dimethoxy-3,5-dihydro-4<i>H</i>-2,3-benzodiazepin-4-ones in high yields instead of the expected alkylation products. The two-dimensional <sup>1</sup>H–<sup>13</sup>C NMR spectra (HSQC, HMBC) of 2-{[1-(4-bromophenyl)-7,8-dimethoxy-5<i>H</i>-2,3-benzodiazepin-4-yl]sulfanyl}-<i>N</i>-phenylacetamide were analyzed.</p>

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S-Alkylation of 1-Aryl-7,8-dimethoxy-3,5-dihydro-4H-2,3-benzodiazepine-4-thiones

  • 期刊论文

  • 发表日期：

    2026年3月1日

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  • V. Yu. Popov,
  • M. A. Orlov,
  • N. V. Glinyanaya

摘要

Abstract

A series of new N-aryl-2-[(1-aryl-7,8-dimethoxy-5H-2,3-benzodiazepin-4-yl)sulfanyl]acetamides were synthesized by the S-alkylation of 1-aryl-7,8-dimethoxy-3,5-dihydro-4H-2,3-benzodiazepine-4-thiones with N-aryl-2-chloroacetamides. The reaction of 2,3-benzodiazepine-4-thiones with chloroacetic acid in the presence of bases afforded the corresponding 1-aryl-7,8-dimethoxy-3,5-dihydro-4H-2,3-benzodiazepin-4-ones in high yields instead of the expected alkylation products. The two-dimensional 1H–13C NMR spectra (HSQC, HMBC) of 2-{[1-(4-bromophenyl)-7,8-dimethoxy-5H-2,3-benzodiazepin-4-yl]sulfanyl}-N-phenylacetamide were analyzed.