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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
P R Latthe P S Shinge Bharati V Badami P B Patil S N Holihosur
Volume 118 Issue 3 May 2006 pp 249-256
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https://www.ias.ac.in/article/fulltext/jcsc/118/03/0249-0256 -
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).
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Author Affiliations
P R Latthe1 P S Shinge1 2 Bharati V Badami1 P B Patil3 S N Holihosur3
- Department of Chemistry, Karnatak University, Dharwad - 580 003
- Department of Organic Chemistry, Indian Institute of Science, Bangalore - 560 012
- Department of Zoology, Karnatak University, Dharwad - 580 003
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Dates
- Published
- May 2006
- Manuscript received
- 1 September 2005
- Manuscript revised
- 4 January 2006
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Journal of Chemical Sciences
Volume 135, 2023
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