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Molecular Diversity

, Volume 19, Issue 4, pp 759–771 | Cite as

A facile environment-friendly one-pot two-step regioselective synthetic strategy for 3,7-diarylpyrazolo[1,5-a]pyrimidines related to zaleplon and 3,6-diarylpyrazolo[1,5-a]pyrimidine-7-amines assisted by KHSO\(_{4}\) in aqueous media

  • Asem Satyapati Devi
  • Shunan Kaping
  • Jai Narain Vishwakarma
Full-Length Paper

Abstract

3-Aminopyrazoles required for the synthesis of pyrazolo[1,5-a]pyrimidines were obtained by the reaction of enaminonitriles with hydrazine hydrate. The resulting aminopyrazoles are reacted with formylated acetophenones under reflux at \(60~ ^\circ \hbox {C}\) assisted by KHSO\(_{4}\) in aqueous media to form regioselectively 3,7-diarylpyrazolo[1,5-a]pyrimidines and 3,6-diarylpyrazolo[1,5-a]pyrimidine-7-amines. X-ray crystallography of selected compounds 5b and 7i further confirmed the regioselective formation of these products.

Keywords

3-Aminopyrazole Michael addition Pyrazolo[1, 5-a]pyrimidines Regioselectivity Zaleplon 

Notes

Acknowledgments

Authors wish to thank Rev. Fr. Dr. Stephen Mavely, Vice Chancellor, Assam Don Bosco University for providing infrastructure for the execution of this work. Authors also wish to express their gratitude to IIT, Guwahati, Tezpur University, Tezpur, SAIF-NEHU, Shillong and SAIF-CDRI, Lucknow for providing spectral and analytical data. Our thanks are also due to the Department of Biotechnology (DBT), Government of India for a research project. SK thanks DBT-GOI for research fellowships.

Supplementary material

11030_2015_9606_MOESM1_ESM.pdf (2.5 mb)
Supplementary material 1 (pdf 2555 KB)
11030_2015_9606_MOESM2_ESM.rar (9 kb)
Supplementary material 2 (rar 9 KB)

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Copyright information

© Springer International Publishing Switzerland 2015

Authors and Affiliations

  • Asem Satyapati Devi
    • 1
  • Shunan Kaping
    • 1
  • Jai Narain Vishwakarma
    • 1
  1. 1.Organic Research Lab., Department of Chemical ScienceAssam Don Bosco UniversityGuwahatiIndia

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