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

      K Nagarajan M D Nair S J Shenoy G Kartha

      Organic Volume 92 Issue 1 January 1983 pp 99-106

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      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/092/01/0099-0106

    • 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

       
      Published
      January 1983
      Manuscript received
      27 September 1982

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