An efficient synthesis of pyrazolo[1,5-a]pyrimidines and evaluation of their antimicrobial activity

作者：Deshmukh Someshwar; Dingore Kunal; Gaikwad Vishwas; Jachak Madhukar^*

来源：Journal of Chemical Sciences, 2016, 128(9): 1459-1468.

DOI：10.1007/s12039-016-1141-x

• Pyrazolo-pyrimidine
• pyrazolyl-pyrazolo-pyrimidine
• deep eutectic solvents
• DES
• alpha-acetyl-gamma-butyrolactone

A series of new pyrazolo[1,5-a]pyrimidine derivatives has been synthesized by using 7-hydrazinyl- 5-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrile 1 and 7-amino-5-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrile 2 as precursors. The pyrazolo[3,4-d] pyrimidines 3a-b have been synthesized by a three-step reaction starting with 1. Compound 1 was utilized for the synthesis of dioxopyrrolidindolinylamio-pyrazolo-pyrimidines 4a-b, and dioxoisoindolin-pyrazolo-pyrimidines 4c-d. Also, compounds 4a-dwere synthesized using deep eutectic solvents (DES). This method using DES provides several advantages such as benign environment, high yield, scalable and simple work-up procedure. Similarly, the cyclocondensation of 2 with alpha-acetyl- gamma-butyrolactone afforded pyrazolo-pyrido-pyrimidine 5 and dihydrofuro-pyrido-pyrazolo-pyrimidine 6. All synthesized compounds were screened for antimicrobial activity.

• 出版日期2016-9