A new and straightforward route to synthesize novel pyrazolo[3,4-]pyridine-5-carboxylate scaffolds from 1,4-dihydropyrano[2,3-]pyrazole-5-carbonitriles

Among many acidic catalysts, amorphous carbon-supported sulfonic acid (AC-SO 3 H) has been evaluated as a new-generation solid catalyst with outstanding activity. Because of the -SO 3 H groups, the surface properties of the amorphous carbon catalyst were improved, which made the catalytic activity o...

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Bibliographic Details
Published in:RSC advances 2023-01, Vol.13 (3), p.1877-1882
Main Authors: Nguyen, Hai Truong, Dang, Phu Hoang, Tran, Phuong Hoang
Format: Article
Language:English
Subjects:
Aniline
Carbon
Cascade chemical reactions
Catalysts
Catalytic activity
Chemistry
Ethanol
Pyrazole
Pyridines
Reaction time
Room temperature
Scaffolds
Sulfonic acid
Sulfuric acid
Surface properties
Surface stability
Synthesis
Toxicity
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Summary:Among many acidic catalysts, amorphous carbon-supported sulfonic acid (AC-SO 3 H) has been evaluated as a new-generation solid catalyst with outstanding activity. Because of the -SO 3 H groups, the surface properties of the amorphous carbon catalyst were improved, which made the catalytic activity of the amorphous carbon-supported sulfonic acid many times greater than that of sulfuric acid. The amorphous carbon-supported sulfonic acid exhibited several advantages such as low cost, non-toxicity, porosity, stability, and easily adjustable chemical surface. In this paper, we introduce a new pathway for the synthesis of pyrazolo[3,4- b ]pyridine-5-carboxylate scaffolds from 1,4-dihydropyrano[2,3- c ]pyrazole-5-carbonitriles and aniline at room temperature under ethanol in the presence of AC-SO 3 H as the catalyst. This method provided the desired products with moderate to good yields. The gram-scale synthesis of the major product was carried out with good yields (up to 80%). This strategy involves a sequential opening/closing cascade reaction. This approach presents several advantages, including room temperature conditions, short reaction time, and operational simplicity. A new pathway for the synthesis of pyrazolo[3,4- b ]pyridine-5-carboxylate scaffolds from 1,4-dihydropyrano[2,3- c ]pyrazole-5-carbonitriles and aniline has been developed using sulfonated amorphous carbon at room temperature.
ISSN:2046-2069
2046-2069
DOI:10.1039/d2ra07521k