Selective Synthesis of New Tetracyclic Coumarin-fused Pyrazolo[3,4-b]pyridines and Pyrazolo[3,4-b]pyridin-6(7H)-ones
Meilin Liu
Hubei Collaborative Innovation Center for Rare Metal Chemistry, Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, Hubei Normal University, Huangshi, 435002 China
Search for more papers by this authorCorresponding Author
Guodong Yin
Hubei Collaborative Innovation Center for Rare Metal Chemistry, Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, Hubei Normal University, Huangshi, 435002 China
E-mail: [email protected]Search for more papers by this authorCan Zhu
Hubei Collaborative Innovation Center for Rare Metal Chemistry, Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, Hubei Normal University, Huangshi, 435002 China
Search for more papers by this authorChaochao Yao
Hubei Collaborative Innovation Center for Rare Metal Chemistry, Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, Hubei Normal University, Huangshi, 435002 China
Search for more papers by this authorMeilin Liu
Hubei Collaborative Innovation Center for Rare Metal Chemistry, Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, Hubei Normal University, Huangshi, 435002 China
Search for more papers by this authorCorresponding Author
Guodong Yin
Hubei Collaborative Innovation Center for Rare Metal Chemistry, Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, Hubei Normal University, Huangshi, 435002 China
E-mail: [email protected]Search for more papers by this authorCan Zhu
Hubei Collaborative Innovation Center for Rare Metal Chemistry, Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, Hubei Normal University, Huangshi, 435002 China
Search for more papers by this authorChaochao Yao
Hubei Collaborative Innovation Center for Rare Metal Chemistry, Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, Hubei Normal University, Huangshi, 435002 China
Search for more papers by this authorAbstract
A three-component reaction for the synthesis of new coumarin-fused tetracyclic system from 4-hydroxycoumarin, aldehydes, and 5-aminopyrazoles/5-aminoisoxazole is described. In the presence of acetic acid, 4,7-dihydro-1H-pyrazolo[3,4-b]pyridines (4) and pyrazolo[3,4-b]pyridines (5) were obtained in acetonitrile and dimethylsulfoxide medium, respectively. The reaction gave rise to 4,5-dihydro-1H-pyrazolo[3,4-b]pyridin-6(7H)-ones (6) in acetic acid–ethanol combination system, which involved the C–O bond cleavage. 4-Hydroxy-6-methyl-2H-pyran-2-one and acenaphthylene-1,2-dione were also examined, affording the corresponding C–O bond cleavage products. Mechanism indicates that the reaction is reversible in acetic acid–ethanol combination system.
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References and Notes
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