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Russian Chemical Bulletin

, Volume 67, Issue 10, pp 1920–1926 | Cite as

Selective O- and N-nitration of steroids fused to the pyrazole ring

  • A. Kh. Shakhnes
  • I. L. Dalinger
  • A. S. Shashkov
  • E. I. Chernoburova
  • M. A. Shchetinina
  • I. V. Zavarzin
Article
  • 6 Downloads

Abstract

Chemoselective methods for O- and N-nitration of steroids fused to the pyrazole ring were developed. The nitrating agents were acetyl, propionyl, and trifluoroacetyl nitrates generated from carboxylic acid anhydrides and either copper nitrate or nitric acid. Depending on the reaction conditions, the developed methods allow both selective nitration at the pyrazole nitrogen atom leaving intact the hydroxy group of steroid framework and dinitration giving rise to the corresponding nitrates of steroidal nitropyrazoles.

Key words

steroids fused to the pyrazole ring O-nitration N-nitration steroidal nitropyrazoles steroidal nitrates copper nitrate nitric acid carboxylic acid anhydrides 

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • A. Kh. Shakhnes
    • 1
  • I. L. Dalinger
    • 1
  • A. S. Shashkov
    • 1
  • E. I. Chernoburova
    • 1
  • M. A. Shchetinina
    • 1
  • I. V. Zavarzin
    • 1
  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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