The catalyst-free syntheses of pyrazolo[3,4-b]quinolin-5-one and pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidin-5,7-dione derivatives by one-pot, three-component reactions

Mahnaz Ezzati, Jabbar Khalafy, Ahmad Poursattar Marjani, Rolf H Prager

Research output: Contribution to journalArticlepeer-review

39 Citations (Scopus)

Abstract

Herein we report the syntheses of pyrazolo[3,4-b]quinolin-5-one and pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidin-5,7-dione derivatives by cyclocondensation of 1,3-diketones, 3-methyl-1-phenyl-1H-pyrazole-5-amine and arylglyoxals, under catalyst-free conditions in H2O/EtOH at reflux in 65–98% and 73–96% yields respectively. This protocol provides mild reaction conditions, good to high yields, non-catalytic, simple procedures and easy isolation of products to structurally diverse tricyclic pyrazolo[3,4-b]quinolin-5-one and pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidin-5,7-dione derivatives, which may have biological and pharmacological activities.

Original languageEnglish
Pages (from-to)6587-6596
Number of pages10
JournalTetrahedron
Volume73
Issue number47
Early online date27 Oct 2017
DOIs
Publication statusPublished - 23 Nov 2017

Keywords

  • Arylglyoxals
  • Multi-component reactions
  • One-pot
  • Pyrazolo[3,4-b]quinolines
  • Pyrido[2,3-d]pyrimidines

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