l-Proline as an efficicent catalyst for the multi-component synthesis of 6-amino-4-alkyl/aryl-3-methyl-2,4-dihydropyrano[2,3- c]pyrazole-5-carbonitriles in water

An efficient four-component synthesis of 6-amino-4-alkyl/aryl-3-methyl-2,4-dihydropyrano[2,3- c]pyrazole-5-carbonitriles involving ethyl acetoacetate, hydrazine hydrate, malononitrile, and various aldehydes using l-proline (10 mol %) in water under mild reaction condition in excellent yields is esta...

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Bibliographic Details
Published in:Tetrahedron letters 2011-06, Vol.52 (25), p.3228-3231
Main Authors: Mecadon, Hormi, Rohman, Md. Rumum, Kharbangar, Iadeishisha, Laloo, Badaker M., Kharkongor, Icydora, Rajbangshi, Mantu, Myrboh, Bekington
Format: Article
Language:English
Subjects:
Catalysis
Catalysts: preparations and properties
Chemistry
Environmentally benign
Exact sciences and technology
Four-component reaction
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
l-Proline
Organic chemistry
Preparations and properties
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Water
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Summary:An efficient four-component synthesis of 6-amino-4-alkyl/aryl-3-methyl-2,4-dihydropyrano[2,3- c]pyrazole-5-carbonitriles involving ethyl acetoacetate, hydrazine hydrate, malononitrile, and various aldehydes using l-proline (10 mol %) in water under mild reaction condition in excellent yields is established. A comparative study of l-proline with γ-alumina, basic alumina, and KF-alumina was also carried out. The generality and functional tolerance of this convergent and environmentally benign method is demonstrated.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.04.048