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

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...

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Bibliographic Details
Published in:Journal of Chemical Sciences 2006-05, Vol.118 (3), p.249-256
Main Authors: Latthe, P. R., Shinge, P. S., Badami, Bharati V., Patil, P. B., Holihosur, S. N.
Format: Article
Language:English
Subjects:
Alcohols
Amines
Antiinfectives and antibacterials
Antimicrobial agents
Carbamates (tradename)
Larvae
Ureas
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Summary: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).
ISSN:0253-4134
0974-3626
0973-7103
DOI:10.1007/BF02708284