Journal of Chemical Sciences

, Volume 129, Issue 10, pp 1579–1586 | Cite as

Synthesis of 7-arylethyl-5-arylpyrazolo\([1{,}5\hbox {-}a]\)pyrimidines through an aza-Michael addition/nucleophilic addition/1,3-hydrogen transfer cascade

  • Zheng Li
  • Demeng Xie
  • Jiaojiao He
  • Yan Du
  • Jingya Yang
Regular Article
  • 124 Downloads

Abstract

An efficient method for the synthesis of pyrazolo\([1{,}5\hbox {-}a]\)pyrimidines by the tandem reactions of dienones with pyrazole-3-amine through an aza-Michael addition/nucleophilic addition/1,3-hydrogen transfer process in the presence of potassium hydroxide is described. This protocol offers access to 7-arylethyl-5-arylpyrazolo\([1{,}5\hbox {-}a]\)pyrimidines in good to excellent yield. Meanwhile for 4-substituted dienones, different products, 7-arylethylene-5-arylpyrazolo\([1{,}5\hbox {-}a]\)pyrimidines, are given through an aza-Michael addition/nucleophilic addition/oxidation process. A gram-scale reaction has been performed to demonstrate the potency of optimized procedure for the scale-up process.

Graphical Abstract

SYNOPSIS7-Arylethyl-5-arylpyrazolo\([1{,}5\hbox {-}a]\)pyrimidines were efficiently synthesized by the reactions of 4-unsubstituted dienones with pyrazole-3-amine. In contrast, 7-arylethylene-5-arylpyrazolo\([1{,}5\hbox {-}a]\)pyrimidines could be afforded by the reactions of 4-substituted dienones with pyrazole-3-amine.

Keywords

Pyrazole-3-amine dienone pyrazolo[1, 5-a]pyrimidine tandem reaction heterocyclization 

Notes

Acknowledgements

The authors thank the National Natural Science Foundation of China (21462038, 21362034) and Key Laboratory of Eco-Environment-Related Polymer Materials of Ministry of Education for the financial support of this work.

Supplementary material

12039_2017_1365_MOESM1_ESM.docx (9 mb)
Supplementary material 1 (docx 9175 KB)

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Copyright information

© Indian Academy of Sciences 2017

Authors and Affiliations

  • Zheng Li
    • 1
  • Demeng Xie
    • 1
  • Jiaojiao He
    • 1
  • Yan Du
    • 1
  • Jingya Yang
    • 1
  1. 1.College of Chemistry and Chemical EngineeringNorthwest Normal UniversityLanzhouPeople’s Republic of China

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