Title:Four-Component Synthesis of pyrano[2,3-c]pyrazoles Catalyzed by Triphenylphosphine in Aqueous Medium
VOLUME: 13 ISSUE: 2
Author(s):Imene Amine Khodja, Amina Fisli, Oumeima Lebhour, Raouf Boulcina, Boudjemaa Boumoud and Abdelmadjid Debache
Affiliation:Laboratoire de Synthèse de Molécules d’Intérêts Biologiques, Université Constantine1, 25000 Constantine, Algérie.
Keywords:Aqueous medium, multicomponent reaction, pyrano[2, 3-c]pyrazoles, triphenylphosphine.
Abstract:Background: The pyrano[2,3-c]pyrazoles have various biological properties such as antiinflammatory,
anti-cancer, antifongical, analgesics and have a potential inhibitor for human ChK1
kinase. For these reasons several synthetic methods are reported. For our part we want to propose a
method which respects the environment.
Method: To achieve our study we used as a model the condensation reaction of hydrazine hydrate, ethyl acetoacetate, benzaldehyde
and malononitrile in the respective proportions of 1/1/1/1 and in the presence of Triphenylphosphine in various
concentrations and different solvents.
Results: We found that the optimal conditions for this reaction are 10 mol% of catalyst in refluxed H2O. Given these results
and to show the generality of the procedure, we applied the optimized reaction conditions for the synthesis of various
dihydropyrano[2,3-c]pyrazoles from a range of substituted aromatic and heteroaromatic aldehydes. We have also applied
these conditions by changing hydrazine by phenylhydrazine. The desired products are obtained in good to excellent
yields.
Conclusion: We describe a simple, efficient and benign method for the dihydropyrano[2,3-c]pyrazoles synthesis by a
four-component condensation between hydrazine (or phenylhydrazine), ethyl acetoacetate, malononitrile and a variety of
aromatic and heteroaromatic aldehydes, catalyzed by Triphenylphosphine.
