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Synthesis of substituted pyrazolo[3,4-d]pyrimidines by reactions of 5-amino-1-phenyl-1H-pyrazole derivatives with N-substituted isatins

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Chemistry of Heterocyclic Compounds Aims and scope

The reaction of N-substituted isatins with 5-amino-1-phenyl-1H-pyrazole-4-carboxamide in refluxing methanol in the presence of excess sodium methoxide led to cyclocondensation with the formation of 1-R-1'-phenyl-1',7'-dihydrospiro[indole-3,6'-pyrazolo[3,4-d]pyrimidine]-2,4'(1H,5'H)-diones. Analogous reaction with 5-amino-1-phenyl-1H-pyrazole-4-carbonitrile was a cascade process that involved the formation of 1-R-4'-(methoxy)-1'-phenyl-1',7'-dihydrospiro[indole-3,6'-pyrazolo[3,4-d]pyrimidine]-2(1H)-ones as intermediates and led to N-R-2-[4-(methoxy)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl]anilines.

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Correspondence to Khidmet S. Shikhaliev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(8), 578–582

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Kosheleva, Y.A., Medvedeva, S.M., Shikhaliev, K.S. et al. Synthesis of substituted pyrazolo[3,4-d]pyrimidines by reactions of 5-amino-1-phenyl-1H-pyrazole derivatives with N-substituted isatins. Chem Heterocycl Comp 52, 578–582 (2016). https://doi.org/10.1007/s10593-016-1935-2

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