The preparation of 3-phenyl[1,2,4]triazolo[4,3-a]pyridines and their benzologs from N-(phenylsulfonyl)benzohydrazonoyl chloride and pyridines.

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  • Ito Suketaka
    Department of Industrial Chemistry, Faculty of Engineering, Shinshu University
  • Kakehi Akikazu
    Department of Industrial Chemistry, Faculty of Engineering, Shinshu University
  • Matsuno Toshiyuki
    Department of Industrial Chemistry, Faculty of Engineering, Shinshu University
  • Yoshida Jun-ichi
    Department of Industrial Chemistry, Faculty of Engineering, Shinshu University

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  • The Preparation of 3-Phenyl[1,2,4]triazolo[4,3-<i>a</i>]pyridines and Their Benzologs from <i>N</i>-(Phenylsulfonyl)benzohydrazonoyl Chloride and Pyridines

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3-Phenyl[1,2,4]triazolo[4,3-a]pyridines were obtained in good yields from N′-[α-(1-pyridinio)benzylidene]benzenesulfonohydrazidates, generated from 2-unsubstituted pyridines and N-(phenylsulfonyl)benzohydrazonoyl chloride (2), by oxidation with chloranil. The reaction of quinoline and isoquinoline with 2 gave 1-phenyl-3-phenylsulfonyl-3,3a-dihydro[1,2,4] triazolo [4,3-a]quinoline and 3-phenyl-1-phenylsulfonyl-1,10b-dihydro [1,2,4]triazolo[3,4-a]isoquinoline respectively, both in good yields; they aromatized to the corresponding triazoles by the 1,2-elimination of benzenesulfinic acid on heating.

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