γ-Alumina as a recyclable catalyst for the four-component synthesis of 6-amino-4-alkyl/aryl-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5- carbonitriles in aqueous medium

Tetrahedron Letters

Volumn 52, Issue 19, 2011, Pages 2523-2525

  Mecadon, Hormi ^a   Rohman, Md Rumum ^a   Rajbangshi, Mantu ^a   Myrboh, Bekington ^a  

^a NORTH EASTERN HILL UNIVERSITY   (India)

Author keywords

Alumina; Four component reaction; Water

Indexed keywords

6 AMINO 4 ALKYL ARYL 3 METHYL 2,4 DIHYDROPYRANO[2,3-C]PYRAZOLE 5 CARBONITRILE; ALUMINUM OXIDE; CYANIDE; GAMMA ALUMINA; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CATALYST; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; COMPARATIVE STUDY; ONE POT SYNTHESIS; SYNTHESIS;

EID: 79953704828     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.03.036     Document Type: Article

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27. General experimental procedure for the synthesis of 6-amino-4-alkyl/aryl- 3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles (5): To a pre-stirred mixture of ethyl acetoacetate (1) (0.26 mL, 2.0 mmol) hydrazine hydrate (2) (0.13 mL, 2.5 mmol) in water (10 mL) was added aldehydes (3) (2.0 mmol) and malononitrile (4) (0.13 g, 2.0 mmol) followed by pre-calcinated γ-alumina (30 mol %). The reaction mixture was then heated at 100 °C and allowed to stir for 35-90 min. On completion of the reaction (monitored by TLC), it was cooled and water was evaporated in vacuo. The residue was treated with boiling methanol-ethyl acetate (1:1) and filtered through a sintered funnel and washed thoroughly with the same solvent. The combined filtrate was evaporated in vacuo to afford the crude product which was recrystallized from ethanol/water (9.5:0.5), or purified by column chromatography over silica gel (100-200 mesh) using methanol/dichloromethane (2:8) as the eluent to afford pure compound 5. Same procedure was followed for the reactions when basic alumina and KF-alumina (30 mol %) were used as catalysts during the comparative study.
28. 4O: C, 60.53; H, 6.47; N, 25.67%; found: C, 60.41; H, 6.39; N, 25.40%.