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Microwave-Mediated InCl3-Catalyzed Three-Component Annelation of Thiadiazinе Ring onto 4-Amino-4H-[1,2,4]Triazole-3-Thiol

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Chemistry of Heterocyclic Compounds Aims and scope

A novel efficient three-component annelation of the thiadiazinyl ring onto 4-amino-4H-[1, 2, 4]triazole-3-thiol, catalyzed by nontoxic, recyclable InCl3 under microwave activation, has been developed. The transformation of 4-amino-5-aryl-4H-[1, 2, 4]triazole-3-thiol into triazolothiadiazine involves chemoselective successive double addition reaction consisting of an InCl3-catalyzed dehydrative nucleophilic addition of amino group to an aromatic aldehyde followed by addition of the resulting Schiff base to cyclohexyl isocyanide. The intramolecular cyclization of the adduct results in 3,6-diaryl-5H-[1, 2, 4]triazolo[3,4-b][1, 3, 4]thiadiazine. The reaction proceeds smoothly with good yields.

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Authors and Affiliations

  1. Laboratory of Green Synthesis, Department of Chemistry, University of Allahabad, Allahabad, 211002, U. P., India

    V. Srivastava

  2. Food Analysis and Research Laboratory, Center of Food Technology, University of Allahabad, Allahabad, 211002, U. P., India

    P. K. Singh

  3. Department of Chemistry, United College of Engineering & Research, Naini, Allahabad, 211010, U. P., India

    P. P. Singh

Authors
  1. V. Srivastava
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  2. P. K. Singh
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  3. P. P. Singh
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Correspondence to P. P. Singh.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 625-630, April, 2014.

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Srivastava, V., Singh, P.K. & Singh, P.P. Microwave-Mediated InCl3-Catalyzed Three-Component Annelation of Thiadiazinе Ring onto 4-Amino-4H-[1,2,4]Triazole-3-Thiol. Chem Heterocycl Comp 50, 573–578 (2014). https://doi.org/10.1007/s10593-014-1509-0

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  • DOI: https://doi.org/10.1007/s10593-014-1509-0

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