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Note | Regular issue | Vol 75, No. 12, 2008, pp.3065-3075
Published online, 10th July, 2008
DOI: 10.3987/COM-08-11455
An Alternative Preparation of Pyrazolo-pyridine Derivatives in Ionic Liquid and Comparison Study on the Reactivity of Thioamide and Amide Group

Xin-Ying Zhang, Xiao-Yan Li, Xue-Sen Fan,* Xia Wang, Gui-Rong Qu,* and Jian-Ji Wang

*School of Chemical and Environmental Sciences, Henan Key Laboratory for Environmental Pollution Control, Henan Normal University, Xinxiang, Henan 453007, P. R. China


A novel and efficient preparation of pyrazolo[3,4-b]pyridine (5) and pyrazolo[3,4-b]pyridin-6-one (8) derivatives from the condensation of arylidenecyanothioacetamide (1) or arylidenecyanoacetamide (7) with 5-amino- 3-methyl-1-phenylpyrazole (4) in [bmim]BF4 is reported for the first time. The mechanism for the formation of 5 from 1 and 4, or 8 from 7 and 4, and the comparison between the reactivity of thioamide group versus amide group are briefly discussed.