A Sulfonic Acid Polyvinyl Pyridinium Ionic Liquid Catalyzes the Multi-Component Synthesis of Spiro-indoline-3,5′-pyrano[2,3-d]-pyrimidines and -Pyrazines

A sulfonated poly-4-vinyl pyridinium (PVPy-IL-B-SO3H) containing an acidic pyridinium/HSO3− ionic liquid moiety was prepared and used as a catalyst for the three-component reaction of malononitrile with 1-alkylindoline-2,3-diones and 1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione or methyl 5-hydroxy-...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Vol. 28; no. 9; p. 3663
Main Authors: Khalaj, Mehdi, Taherkhani, Mahboubeh, Payen, Leo, Klein, Axel
Format: Journal Article
Language:English
Published: Switzerland MDPI AG 23.04.2023
MDPI
Subjects:
Chromatography
polymeric ionic liquid
Polymers
polyvinyl pyridine
Pyrimidines
Solvents
spiro-indoline-3,4′-pyrano[2,3-c]pyrazole
spiro-indoline-3,5′-pyrano[2,3-d]pyrimidine
Sulfuric acid
ultrasonic
Germany
United States > US
spiro-indoline-3,5′-pyrano[2,3-d]pyrimidine
spiro-indoline-3,4′-pyrano[2,3-c]pyrazole
polymeric ionic liquid
ultrasonic
polyvinyl pyridine
ISSN:1420-3049, 1420-3049
Online Access:Get full text
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Summary:A sulfonated poly-4-vinyl pyridinium (PVPy-IL-B-SO3H) containing an acidic pyridinium/HSO3− ionic liquid moiety was prepared and used as a catalyst for the three-component reaction of malononitrile with 1-alkylindoline-2,3-diones and 1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione or methyl 5-hydroxy-1H-pyrazole-3-carboxylate, leading to methyl 6′-amino-5′-cyano-2-oxo-2′H-spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-3′-carboxylates or -3,4′-pyrano[2,3-d]pyrimidine]-6′-carbonitrile derivatives under ultrasonic irradiation conditions. The solid catalyst allows easy separation, is cheap, produces high yields under mild conditions, and does not require column chromatography for product isolation and purification.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28093663