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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 10, pp 943–955 | Cite as

Regioselective Synthesis of 1,3,5-Trisubstituted Pyrazoles Containing an Anthranilic Acid Motif

  • Viktor A. Savel’ev
  • Anna A. Kotova
  • Tatyana V. Rybalova
  • Elvira E. ShultsEmail author
Article
  • 36 Downloads

An effective method was developed for the synthesis of 1,3,5-trisubstituted pyrazoles by using acetylenic ketones, obtained from ethyl 5-ethynylanthranilate, in reactions with substituted hydrazines and hydrazides. It was shown that the cyclization of ethyl 5-(3-aryl-3-oxopropinyl)- anthranilates with arylhydrazines proceeded regioselectively and led to the formation of 1,3,5-trisubstituted pyrazoles containing an anthranilate moiety at the position С-3. Significant deterioration of regioselectivity was observed in the reactions of ethyl 5-(3-aryl-3-oxopropinyl)anthranilates with N-methyl- and N-tert-butylhydrazines. The initial products formed in reactions of ethyl 5-[3-(4-fluorophenyl)-3-oxopropinyl]anthranilate with benzoyl and isonicotinoyl hydrazides were 5-hydroxypyrazolines, which underwent dehydration in the presence of pyridine and thionyl chloride in benzene, giving the respective 1,3,5-trisubstituted pyrazoles.

Keywords

alkynyl ketones ethynyl anthranilates hydrazines pyrazoles cyclization X-ray structural analysis 

Notes

ACKNOWLEDGEMENT

This work received financial support from the Russian Science Foundation (grant 18-13-00361).

The analytical and spectral studies were performed at the Collective Use Center for chemical studies at the Siberian Branch of the Russian Academy of Sciences.

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Viktor A. Savel’ev
    • 1
  • Anna A. Kotova
    • 1
    • 2
  • Tatyana V. Rybalova
    • 1
    • 2
  • Elvira E. Shults
    • 1
    • 2
    Email author
  1. 1.N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of SciencesNovosibirskRussia
  2. 2.Novosibirsk State UniversityNovosibirskRussia

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