Amberlyst A21 Catalyzed Chromatography-Free Method for Multicomponent Synthesis of Dihydropyrano[2,3‑<i>c</i>]pyrazoles in Ethanol
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Abstract
Amberlyst
A21 was found to be an extremely efficient catalyst for
synthesis of a series of 6-amino-4-alkyl/aryl-3-methyl-2,4-dihydropyrano[2,3-<i>c</i>]pyrazole-carbonitriles by a four-component reaction of
a mixture of ethyl acetoacetate, hydrazine hydrate, aldehyde, and
malononitrile in ethanol at room temperature. The catalytic efficiency
of Amberlyst A21 was compared with some other resin-bound free and
anionic bases in order to ascertain the best catalyst for the said
conversion. The catalyst was found to work extremely well also for
acyclic/cyclic ketones to give corresponding dihydropyrano[2,3-<i>c</i>]pyrazoles or their spirocyclic variants. Easy recovery
of the catalyst and its reusability, room temperature reaction conditions,
short reaction time, excellent yields, no chromatographic purification,
and evasion of environmentally hazardous solvents in the entire reaction
process may make this protocol very useful for academia and industry