Efficient One-Step Synthesis of Substituted-pyrazolo[3,4-b]pyridine from Substituted-3-cyano-2(1H)-pyridone

Author(s): Yasser S. Abdel-Ghany, Aly A. Hazzaa, Mohamad M. Abdul Ghani, Zahra A. Kassem.

Journal Name: Letters in Organic Chemistry

Volume 5 , Issue 4 , 2008

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Abstract:

An efficient one-step conversion of 4-phenyl-5-ethoxycarbonyl-3-cyano-6-metlyl-2(1H)-pyridone (1) into ethyl 3-amino-6-methyl-4-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (7) is described. An unusual hydrazine mediated decarboxylation of 7 into 3-amino-6-methyl-4-phenyl-1H-pyrazolo[3,4-b]pyridine (8) is reported. The structure of 8 was confirmed by spectral and chemical investigations. A plausible reaction mechanism for the formation of the unexpected product 8 is proposed.

Keywords: One-step conversion, cyanopyridone, pyrazolo[3,4-b]pyridine, hydrazine, decarboxylation

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Article Details

VOLUME: 5
ISSUE: 4
Year: 2008
Page: [316 - 318]
Pages: 3
DOI: 10.2174/157017808784049416
Price: $58

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