Unraveling the access to the regioselective synthesis of highly functionalized pyranopyrazoles using an ionic liquid catalyst

An efficient and green strategy for the regioselective synthesis of highly functionalized pyranopyrazole via one-pot condensation of 3-methyl-1-phenyl-5-pyrazolone or EAA and hydrazine hydrate, substituted aromatic aldehydes with NMSM [( E )-N-Methyl-1-(methylthio)-2-nitro-ethenamine] in the existen...

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Bibliographic Details
Published in:Molecular diversity 2023-12, Vol.27 (6), p.2633-2649
Main Authors: Katariya, Ashishkumar P., Shirsath, Prakash D., Narode, Hanuman, Gaikwad, Pravinkumar B., Kadam, Gajanan G., Katariya, Maya V., Deshmukh, Satish U.
Format: Article
Language:English
Subjects:
Aldehydes
Biochemistry
Biomedical and Life Sciences
Chemistry
Ethanol
Life Sciences
Organic Chemistry
Original Article
Pharmacy
Polymer Sciences
Solvents
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Summary:An efficient and green strategy for the regioselective synthesis of highly functionalized pyranopyrazole via one-pot condensation of 3-methyl-1-phenyl-5-pyrazolone or EAA and hydrazine hydrate, substituted aromatic aldehydes with NMSM [( E )-N-Methyl-1-(methylthio)-2-nitro-ethenamine] in the existence of IL [(EMIM)Ac] as catalyst with solvent-free condition (SFC) is described. This domino protocol produces biologically substantial heterocycles through Knoevenagel condensation proceeded by Michael addition and O -cyclization with an eradication of methanethiol group, which create the one stereo-center and creation of “C–C, C–N, C–O, C=C, C=N, bonds.” The final product is produced by exceptionally easy filtering after the reaction mass was triturated with ethanol. The strategy's noteworthy features include the use of biodegradable IL catalyst, excellent to exceptional yield with rapid reaction times, applicability to a wide range of substrate, clear reaction profile, and straightforward workup process. Graphical abstract
ISSN:1381-1991
1573-501X
DOI:10.1007/s11030-022-10572-9