Rapid Multicomponent Tandem Annulation in Ionic Liquids: Convergent Access to 3-Amino-1-Alkylpyridin-2(1H)-One Derivatives as Potential Anticancer Scaffolds

An efficient, one-pot multicomponent synthesis of 3-amino-1-alkylpyridin-2(1H)-one as privileged medicinal scaffolds was achieved by condensation of N-Alkyl-2-cyanoacetamides, aldehydes, and malononitriles in the presence of 1,8-diazabicyclo [5,4,0] undec-7-enium acetate [DBUH][OAc] ionic liquid, wh...

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Bibliographic Details
Published in:Polycyclic aromatic compounds 2022-11, Vol.42 (10), p.6946-6965
Main Authors: Jadhav, Chetan K., Nipate, Amol S., Chate, Asha V., Kulkarni, Makrand V., Dofe, Vidya S., Gill, Charansingh H.
Format: Article
Language:English
Subjects:
3-amino-1-alkylpyridin-2(1H)-one
[DBUH][OAc]
Acetic acid
Aldehydes
Anticancer properties
Antitumor activity
Chemical reactions
Dihydropyridine
in-vitro antitumor activity
ionic liquid
Ionic liquids
Multicomponent reaction
Recyclability
Scaffolds
Tumor cell lines
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Summary:An efficient, one-pot multicomponent synthesis of 3-amino-1-alkylpyridin-2(1H)-one as privileged medicinal scaffolds was achieved by condensation of N-Alkyl-2-cyanoacetamides, aldehydes, and malononitriles in the presence of 1,8-diazabicyclo [5,4,0] undec-7-enium acetate [DBUH][OAc] ionic liquid, which acts as a green solvent medium. Mild conditions with outstanding conversion and simple isolation procedure are significant advantages of this method. The recyclability and recovery of the ionic liquid make this protocol environmentally desirable. Also, a series of (aryl or het) 2-dihydropyridine-3,5-dicarbonitrile derivatives were evaluated for their in vitro antitumor activity against three human cancer cell lines MCF-7/AZ, HeLa, and Jurkat with promising activity.
ISSN:1040-6638
1563-5333
DOI:10.1080/10406638.2021.1994427