• Addition products of dimethyl acetylenedicarboxylate to thioureas—Studies on 2-(p-bromophenyl) imino-3-methyl-5-carbomethoxymethylidenethiazolidin-(4)-one

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    • Keywords


      Thiazolidinone; thiourea; addition products; dimethyl acetylenedicarboxylate

    • Abstract


      N-(p-bromophenyl)-N’-methylthiourea (1) undergoes addition to acetylenedicarboxylic acid (3) and its dimethyl ester (4) to form 2-(p-bromophenyl) imino-3-methyl-5-carboxymethylidenethiazolidin-(4)-one (5) and its methyl ester (6) respectively. Alkaline hydrolysis of (6) leads to a mixture of (5) and 2-(p-bromophenyl) imino-3,4-dihydro-3-methyl-4-oxo-2H (1,3)-thiazine-6-carboxylic acid (7). Several reactions of (5) and (7) are described. The structures of (5) and (7) are established by x-ray crystallographic and13Cnmr studies.

    • Author Affiliations


      K Nagarajan1 M D Nair1 S J Shenoy1 G Kartha2

      1. Ciba-Geigy Research Centre, Bombay - 400 063, India
      2. Roswell Park Memorial Institute, Buffalo, New York - 14263, USA
    • Dates

  • Journal of Chemical Sciences | News

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