NaF-catalyzed efficient one-pot synthesis of dihydropyrano[2,3-c]pyrazoles under ultrasonic irradiation via MCR approach

Sodium fluoride was identified as an efficient catalyst for the preparation of series of dihydropyrano [2,3-c]pyrazoles (4a-l) by the three-component condensation of 3-Methyl-1-phenyl-2-pyrazoline-5-one (1), aromatic aldehydes (2) and malononitrile (3) in aqueous methanol at ambient temperature unde...

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Bibliographic Details
Published in:Synthetic communications 2018-08, Vol.48 (15), p.1994-2001
Main Authors: Konakanchi, Ramaiah, Gondru, Ramesh, Nishtala, Venkata Bharat, Kotha, Laxma Reddy
Format: Article
Language:English
Subjects:
Aldehydes
Ambient temperature
Aqueous ethanol
Catalysis
Catalysts
cavitation effect
Chemical synthesis
Condensates
Malononitrile
multi-component reaction
NMR
Nuclear magnetic resonance
Reaction time
Sodium fluoride
ultrasonication
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Summary:Sodium fluoride was identified as an efficient catalyst for the preparation of series of dihydropyrano [2,3-c]pyrazoles (4a-l) by the three-component condensation of 3-Methyl-1-phenyl-2-pyrazoline-5-one (1), aromatic aldehydes (2) and malononitrile (3) in aqueous methanol at ambient temperature under ultrasonication. The cost and efficacy of the catalyst, mild reaction conditions, simple workup procedure, less reaction time and higher yields of the product with analytical purity keeping this protocol superior to the previously reported ones. Structures of all the compounds were in agreement with their spectroscopic data ( 1 H NMR, 13 C NMR) and elemental (CHN) analyses.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2018.1479758