Submit Manuscript  

Article Details


Green Synthesis of 1H-pyrazolo[1,2-b]phthalazinedione-2-carbonitriles in the Presence of L-proline

[ Vol. 8 , Issue. 3 ]

Author(s):

Davood Habibi*, Saeedeh Shojaei and Somayyeh Heydari   Pages 321 - 329 ( 9 )

Abstract:


Background: Pyrazolophthalazinedione derivatives show various biological activities such as anti-bacterial, anti-cancer, anti-coagulant, anti-convulsant, anti-fungal, anti-hypoglycemic, anti-inflammatory, anti-tumor, anti-viral, cardiotonic, cytotoxic and vasorelaxant activities.

Objective: The purpose of this study was to synthesize compounds that have various medicinal properties.

Methods: Diverse 3-amino-5,10-dioxo-1-phenyl-5,10-dihydro-1H-pyrazolo[1,2-b]phthal-azine-2-- carbonitriles were synthesized from the one-pot three components green synthesis of phthalhydrazides, aromatic aldehydes and malononitrile in the presence of the proline organocatalyst in ethanol at reflux conditions in excellent yields.

Results: Proline was used as an efficient organocatalyst for the one-pot three components green synthesis of diverse pyrazolophthalazinecarbonitriles. In the absence of the proline organocatalyst, the yield was very low. Also, electron withdrawing or electron releasing groups don’t have a meaningful effect on the reaction times and the structures of all products were in agreement with their IR and NMR spectra.

Conclusion: In the IR spectra, the appearance of the sharp NH2 and the CN peaks at about 3300 and 2300 cm-1, respectively confirm formation of the products.

Keywords:

Pyrazolophthalazinecarbonitriles, phthalhydrazides, malononitrile, aldehydes, proline, green synthesis.

Affiliation:

Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683

Graphical Abstract:



Read Full-Text article