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Russian Chemical Bulletin

, Volume 61, Issue 2, pp 469–471 | Cite as

Nitropyrazoles 22. On reactivity of 3,5-dinitro-4-(phenylsulfonyl)pyrazole and its N-methyl derivative

  • I. A. Vatsadze
  • I. L. Dalinger
  • T. K. Shkineva
  • G. P. Popova
  • S. A. Shevelev
Brief Communications

Abstract

3,5-Dinitro-4-(phenylsulfonyl)pyrazole (5) obtained by oxidation of 3,5-dinitro-4-(phenylthio)pyrazole with 30% H2O2 in AcOH was involved into nucleophilic substitution reaction with thiophenol, which proceeded with substitution of the phenylsulfonyl group at position 4. N-Methyl-3,5-dinitro-4-(phenylsulfonyl)pyrazole obtained by methylation of 5 with dimethyl sulfate was involved into nucleophilic substitution reaction with thiophenol, p-bromophenol, and morpholine with the regioselective substitution of the nitro group at position 5 to form 5-R-3-nitro-4-(phenylsulfonyl)pyrazoles.

Key words

pyrazole nitro group nitropyrazoles 3,5-dinitropyrazoles (phenylsulfonyl)nitropyrazoles nucleophilic substitution nucleophiles regioselective substitution methylation 

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Copyright information

© Springer Science+Business Media New York 2012

Authors and Affiliations

  • I. A. Vatsadze
    • 1
  • I. L. Dalinger
    • 1
  • T. K. Shkineva
    • 1
  • G. P. Popova
    • 1
  • S. A. Shevelev
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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