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

• Published in: Molecular diversity 2016-05, Vol.20 (2), p.379-390
• Main Authors: Kaping, Shunan, Boiss, Ivee, Singha, Laishram Indira, Helissey, Philippe, Vishwakarma, Jai N.
• Format: Article
• Language: English
• ISSN: 1381-1991; 1573-501X
• DOI: 10.1007/s11030-015-9639-6

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.