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    • Reactions of cyclic anhydrides. Part XXII. Direct synthesis of N-aryl-α-(2,3,4,5-tetrahydro-2-imino-4-oxo-1,3-thiazoIe-5-yl) acetamides

      V Balasubramaniyan P Balasubramaniyan M J Wani

      Organic Volume 103 Issue 5 October 1991 pp 621-629

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      https://www.ias.ac.in/article/fulltext/jcsc/103/05/0621-0629

    • Keywords

       

      Thiourea; thiazolidines; mass spectral fragmentation; fumaranilic acids; Raney nickel desulphurisation

    • Abstract

       

      Maleimides (2a−j) react with thiourea in refluxing ethanol to yield the corresponding N-aryl α-(2,3,4,5-tetrahydro-4-oxo-l,3-thiazole-5-yl) acetamides (6a−j) in 72–85%. The spectral and analytical data are consistent with the assigned structures for6a−j. Under similar conditions, isomalemides (3a−b and3d−f) furnish the corresponding6a−b and6d−f in 76–86%. While maleanilic acid (4a) itself failed to react with thiourea,4b−ē,4i and4j yielded a mixture of the corresponding6b−ē,6i and6j in 2–50% and fumaranilic acids (7b−ē,7i and7j) in 50–80%. Methyl maleanilates (5b,5d−f and5i) gave6b,6d−f and6i in 78–85%. The reaction course of Raney nickel desulphurisation of6a−b,6d,6f and mass spectral fragmentation of6b support the assigned structures.

    • Author Affiliations

       

      V Balasubramaniyan1 P Balasubramaniyan1 M J Wani1

      1. Science Research Centre, HPT Arts and RYK Science College, Nashik - 422 005, India

    • Dates

       
      Published
      October 1991
      Manuscript received
      30 July 1990
      Manuscript revised
      5 February 1991

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