European Journal of Chemistry 2020, 11(3), 179-186 | doi: https://doi.org/10.5155/eurjchem.11.3.179-186.1977 | Get rights and content






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A three step one-pot regioselective synthesis of highly substituted pyrazolo[1,5-a]pyrimidines assisted by KHSO4 in aqueous media under ultrasound irradiation


Shunan Kaping (1) orcid , Philippe Helissey (2) orcid , Jai Narain Vishwakarma (3,*) orcid

(1) Organic Research Laboratory, Department of Chemical Science, Assam Don Bosco University, Tapesia Gardens, Sonapur 782402, Assam, India
(2) Laboratoire de Chimie Thérapeutique, UMR CNRS No. 8638, Université Paris Descartes, Faculte des Sciences Pharmaceutiqueset Biologiques, Paris, France
(3) Organic Research Laboratory, Department of Chemical Science, Assam Don Bosco University, Tapesia Gardens, Sonapur 782402, Assam, India
(*) Corresponding Author

Received: 29 Feb 2020 | Revised: 06 Jun 2020 | Accepted: 12 Jun 2020 | Published: 30 Sep 2020 | Issue Date: September 2020

Abstract


A simple and efficient synthesis of substituted pyrazolo[1,5-a]pyrimidine derivatives has been developed by the use of ultrasound. 5-Methyl-4-phenyl-1H-pyrazol-3-amine required for the synthesis of pyrazolo[1,5-a]pyrimidine derivatives has been easily obtained by the reaction of 3-(dimethylamino)-2-phenylacrylonitrile (formed from readily available 2-phenylacetonitrile) with hydrazine hydrate in refluxing ethanol. The 5-aminopyrazole was then reacted with various formylated active proton compounds in presence of KHSO4 in aqueous medium under ultrasound irradiation to give the desired products. The chemical structures of the newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR and Mass spectral data. X-ray crystallographic study of a selected compound 6-(4-chlorophenyl)-2-methyl-3-phenylpyrazolo[1,5-a]pyrimidin-7-amine (7c) was performed to ascertain the regioselectivity of the reaction. Crystal data for compound 7c: Triclinic, space group P-1 (no. 2), a = 8.0198(3) Å, b = 14.0341(6) Å, c = 14.2099(6) Å, α = 87.672(2)°, β = 83.902(2)°, γ = 89.120(2)°, = 1588.87(11) Å3, Z = 4, T = 293(2) K, μ(MoKα) = 0.248 mm-1, Dcalc = 1.400 g/cm3, 12918 reflections measured (4.012° ≤ 2Θ ≤ 49°), 5152 unique (Rint = 0.0411, Rsigma = 0.0429) which were used in all calculations. The final R1 was 0.0486 (I > 2σ(I)) and wR2 was 0.1320 (all data).


Keywords


Enaminones; X-ray structure; One pot procedure; Pyrazolopyrimidine; Ultrasound irradiation; Pyrazolo[1,5-a]pyrimidines

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DOI: 10.5155/eurjchem.11.3.179-186.1977

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Funding information


Department of Biotechnology, Government of India, New Delhi, India.

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Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Kaping, S.; Helissey, P.; Vishwakarma, J. Eur. J. Chem. 2020, 11(3), 179-186. doi:10.5155/eurjchem.11.3.179-186.1977
Kaping, S.; Helissey, P.; Vishwakarma, J. A three step one-pot regioselective synthesis of highly substituted pyrazolo[1,5-a]pyrimidines assisted by KHSO4 in aqueous media under ultrasound irradiation. Eur. J. Chem. 2020, 11(3), 179-186. doi:10.5155/eurjchem.11.3.179-186.1977
Kaping, S., Helissey, P., & Vishwakarma, J. (2020). A three step one-pot regioselective synthesis of highly substituted pyrazolo[1,5-a]pyrimidines assisted by KHSO4 in aqueous media under ultrasound irradiation. European Journal of Chemistry, 11(3), 179-186. doi:10.5155/eurjchem.11.3.179-186.1977
Kaping, Shunan, Philippe Helissey, & Jai Narain Vishwakarma. "A three step one-pot regioselective synthesis of highly substituted pyrazolo[1,5-a]pyrimidines assisted by KHSO4 in aqueous media under ultrasound irradiation." European Journal of Chemistry [Online], 11.3 (2020): 179-186. Web. 30 Oct. 2020
Kaping, Shunan, Helissey, Philippe, AND Vishwakarma, Jai. "A three step one-pot regioselective synthesis of highly substituted pyrazolo[1,5-a]pyrimidines assisted by KHSO4 in aqueous media under ultrasound irradiation" European Journal of Chemistry [Online], Volume 11 Number 3 (30 September 2020)

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DOI Link: https://doi.org/10.5155/eurjchem.11.3.179-186.1977

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