• Curtius rearrangement reactions of 3-(4-azidocarbonyl) phenylsydnone. Synthesis of 4-(sydnon-3-yl) phenyl carbamates, N-aryl-N′-[4-(sydnon-3-yl)] phenyl ureas and their antimicrobial and insecticidal activities

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    • Keywords

       

      3-(4-Azidocarbonyl)phenylsydnone; Curtius rearrangement; 4-(sydnon-3-yl)phenyl carbamates; N-aryl-N′-[4-(sydnon-3-yl)] phenyl ureas

    • Abstract

       

      3-[4-(Azidocarbonyl)]phenylsydnone (2) obtained from 3-(4-hydrazinocarbonyl) phenylsydnone (1) on Curtius rearrangement with alcohols, water and amines afforded the corresponding carbamates (3a-h), 4,4′-(sydnone-3-yl) diphenyl urea (4) and 4-(heterocyclyl)phenyl ureas (5a-l). Compounds (5a-l) on one-pot ring conversion yielded the 1,3,4-oxadiazolin-2-one derivatives (6a-l), which on reaction with N2H4 gave the 4-amino-1,2,4-triazolin-3-ones (7a-l). All these compounds exhibited moderate antimicrobial activity against the few microbes tested. The carbamates have been found to be more toxic against fourth instar larvae ofAedes aegypti, in particular, then-butyl derivative (3e).

    • Author Affiliations

       

      P R Latthe1 P S Shinge1 2 Bharati V Badami1 P B Patil3 S N Holihosur3

      1. Department of Chemistry, Karnatak University, Dharwad - 580 003
      2. Department of Organic Chemistry, Indian Institute of Science, Bangalore - 560 012
      3. Department of Zoology, Karnatak University, Dharwad - 580 003
    • Dates

       
  • Journal of Chemical Sciences | News

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