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A facile, regioselective synthesis of novel 3-(N-phenylcarboxamide)pyrazolo[1,5-a]pyrimidine analogs in the presence of KHSO\(_{4}\) in aqueous media assisted by ultrasound and their antibacterial activities

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Abstract

An environmentally benign, simple, efficient, and convenient route is described for the synthesis of novel pyrazolo[1,5-a]pyrimidine derivatives under ultrasound irradiation. Condensation of aminopyrazole 5 with formylated active proton compounds (6, 8, E–G, 12, and 15) furnished pyrazolopyrimidine (7, 9, 10, 13, and 16) in high-to-excellent yields. In comparison with conventional methods, ultrasound irradiation offers several advantages, such as shorter reaction time, higher yields, milder conditions, and environmental friendliness. The reaction is clean with excellent yields and reduces the use of solvents. X-ray crystallographic study of compound 7c confirmed the regioselectivity of the reaction. The antibacterial profile of the newly synthesized compounds was evaluated by cup and saucer method.

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Acknowledgments

The authors wish to thank Rev. Fr. Dr. Stephen Mavely, Vice Chancellor, Assam Don Bosco University for providing infrastructure for the execution of this work. The authors also wish to express their gratitude to the IIT, Guwahati; Tezpur University, Tezpur; SAIF-NEHU, Shillong; and SAIF-CDRI, Lucknow. Our thanks are also due to the Department of Biotechnology (DBT), Government of India for a research Grant. SK thanks NER-BPMC-DBT, New Delhi for the award of a research fellowship.

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Authors and Affiliations

  1. Organic Research Laboratory, Department of Chemical Science, Assam Don Bosco University, Airport Road-Azara, Guwahati, 781017, India

    Shunan Kaping & Jai N. Vishwakarma

  2. Laboratoire de Chimie Thérapeutique, UMR CNRS No. 8638, Université Paris Descartes, Faculte des Sciences Pharmaceutiques et Biologiques, 75270, Paris Cedex 06, France

    Philippe Helissey

  3. Department of Biotechnology, St. Anthonys College, Shillong, 793001, India

    Ivee Boiss & Laishram Indira Singha

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  1. Shunan Kaping
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  2. Ivee Boiss
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Correspondence to Jai N. Vishwakarma.

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CIF files for compound 7c 17 KB

1H NMR, 13C NM Mass Spectra 1855 KB

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Kaping, S., Boiss, I., Singha, L.I. et al. A facile, regioselective synthesis of novel 3-(N-phenylcarboxamide)pyrazolo[1,5-a]pyrimidine analogs in the presence of KHSO\(_{4}\) in aqueous media assisted by ultrasound and their antibacterial activities. Mol Divers 20, 379–390 (2016). https://doi.org/10.1007/s11030-015-9639-6

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