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Chemistry of Heterocyclic Compounds

, Volume 52, Issue 8, pp 578–582 | Cite as

Synthesis of substituted pyrazolo[3,4-d]pyrimidines by reactions of 5-amino-1-phenyl-1H-pyrazole derivatives with N-substituted isatins

  • Yevgeniya A. Kosheleva
  • Svetlana M. Medvedeva
  • Khidmet S. ShikhalievEmail author
  • Fedor I. Zubkov
  • Elena A. Ryzhkova
  • Mikhail A. Prezent
Article

The reaction of N-substituted isatins with 5-amino-1-phenyl-1H-pyrazole-4-carboxamide in refluxing methanol in the presence of excess sodium methoxide led to cyclocondensation with the formation of 1-R-1'-phenyl-1',7'-dihydrospiro[indole-3,6'-pyrazolo[3,4-d]pyrimidine]-2,4'(1H,5'H)-diones. Analogous reaction with 5-amino-1-phenyl-1H-pyrazole-4-carbonitrile was a cascade process that involved the formation of 1-R-4'-(methoxy)-1'-phenyl-1',7'-dihydrospiro[indole-3,6'-pyrazolo[3,4-d]pyrimidine]-2(1H)-ones as intermediates and led to N-R-2-[4-(methoxy)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl]anilines.

Keywords

o-aminonitriles 5-aminopyrazole derivatives pyrazolo[3,4-d]pyrimidines spiro[indole-3,6'-pyrazolo[3,4-d]pyrimidines] N-substituted isatins 

Supplementary material

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Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  • Yevgeniya A. Kosheleva
    • 1
  • Svetlana M. Medvedeva
    • 1
  • Khidmet S. Shikhaliev
    • 1
    Email author
  • Fedor I. Zubkov
    • 2
  • Elena A. Ryzhkova
    • 2
  • Mikhail A. Prezent
    • 3
  1. 1.Voronezh State UniversityVoronezhRussia
  2. 2.People’s Friendship University of RussiaMoscowRussia
  3. 3.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussia

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