NDLI: Solvent-free, one-pot synthesis and biological evaluation of some new dipyrazolo [3,4-b:4′,3′-e]pyranylquinolones and their precursors

Content Provider	Springer Nature Link
Author	Parmar, Narsidas J. Pansuriya, Bhavesh R. Parmar, Bhagyashri D. Barad, Hitesh A.
Copyright Year	2013
Abstract	One-pot synthesis of 24 new compounds, belonging to three families; dipyrazolo[3,4-b:4′,3′-e]pyranylquinolones 7a–h and its precursors (pyrazolonylidene)methylquinolones 5a–h and 4,4′-[(quinolinyl)methylene]bispyrazols 6a–h, 8 from each, has been achieved in the presence of catalyst tetrabutylammonium hydrogen sulfate (TBA–HS) in solvent-free conditions. In addition to assuring chromatography-free product isolation, this method had also allowed the reaction to proceed in a regio-selective manner provided the temperature and amount of pyrazolone are varied. At 100 °C, while 1:1 mixture of aldehyde 3 and pyrazolone 4 underwent Knoevenagel condensation, same reactants taken in ratio of 1:2 mainly domino/Knoevenagel–Michael reaction. At 120 °C, however, the domino/Knoevenagel–Michael-adducts converted into cyclized product, highlighting a new domino/Knoevenagel–Michael-cyclization synthetic sequence. The structure of all heterocycles has been confirmed by mass, IR and NMR spectral data. Based on 2D NMR NOESY experiment, it was also confirmed that the formation of only ‘Z’ configuration of Knoevenagel alkene took place in the transformation. All are good antitubercular agents as they were found to be active against M. tuberculosis H37RV, in addition to being found active against three Gram-positive (Streptococcus pneumoniae, Clostridium tetani, Bacillus subtilis) and three Gram-negative (Salmonella typhi, Vibrio cholerae, Escherichia coli) bacteria, respectively.
Starting Page	42
Ending Page	56
Page Count	15
File Format	PDF
ISSN	10542523
Journal	Medicinal Chemistry Research
Volume Number	23
Issue Number	1
e-ISSN	15548120
Language	English
Publisher	Springer US
Publisher Date	2013-05-16
Publisher Place	New York
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Knoevenagel–Michael Tetrabutyl ammonium hydrogen sulfate 3-Methyl-1-phenyl-5-pyrazolone Bis-Pyrazole N-Allyl quinolone Pharmacology/Toxicology Biochemistry Cell Biology
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Pharmacology, Toxicology and Pharmaceutics

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