European Journal of Chemistry

Efficient synthesis of diversely substituted pyrazolo[1,5-a]pyrimidine derivatives promoted by ultrasound irradiation in water and their antibacterial activities

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Susma Das
Shilpika Khanikar
Shunan Kaping
Jayanti Datta Roy
Arnab Sen
Philippe Helissey
Jai Narain Vishwakarma

Abstract

A green synthetic route leading to the discovery of a series of diversely substituted pyrazolo[1,5-a]pyrimidines, having CO2Et group embedded at position-2 has been unraveled in this article. A series of formylated active proton compounds that were chosen to react with a carboxylate substituted-3-aminopyrazole under ultrasonic irradiation in the presence of a mild acid as a catalyst and aqueous ethanol medium afforded the desired products. The molecular structures of all these synthesized compounds were established by their spectral and analytical data. A model molecule 3d, subjected to single-crystal X-ray crystallography analysis further confirms their molecular structure. The crystal crystallized to a monoclinic cell with P21/c space group, a = 7.468 (5) Å, b = 27.908 (17) Å, c = 7.232 (4) Å, β = 104.291 (7)o, V =1460.7(15) Å3, Z = 4, μ(MoKα) = 0.096 mm-1, Dcalc = 1.352 Mg/m3 16667 measured reflection (5.63 ≤ 2Θ ≤ 57.57°), 3720 unique (Rint = 0.0965, Rsigma = 0.0945) which were used in all calculations. The final R1 was 0.0750 (I > 2σ(I)) and wR2 was 0.2226 (all data). These compounds were further explored for their antibacterial potential, and a few of them have exhibited encouraging results.


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Das, S.; Khanikar, S.; Kaping, S.; Roy, J. D.; Sen, A.; Helissey, P.; Vishwakarma, J. N. Efficient Synthesis of Diversely Substituted pyrazolo[1,5-a]pyrimidine Derivatives Promoted by Ultrasound Irradiation in Water and Their Antibacterial Activities. Eur. J. Chem. 2020, 11, 304-313.

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Author Biographies

Jayanti Datta Roy, Indian Council of Agricultural Research Complex for North Eastern Hill Region, Umiam 793103, Meghalaya, India


Arnab Sen, Indian Council of Agricultural Research Complex for North Eastern Hill Region, Umiam 793103, Meghalaya, India


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Supporting Agencies

Department of Biotechnology, Ministry of Science and Technology, Government of India, New Delhi-110 003, India and Indian Council of Agricultural Research (ICAR)-Barapani, Shillong, India.
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