Multi-Component Syntheses of Spiro[furan-2,3′-indoline]-3-carboxylate Derivatives Using Ionic Liquid Catalysts

Two previously described Brønsted acidic ionic liquids, 3,3′-(1,6-hexanediyl)bis(1-methyl)-1H-imidazolium hydrogen sulfate (Cat1) and 1,1′-(1,6-hexanediyl)bis(pyridinium) hydrogen sulfate (Cat2), were used as catalysts for the preparation of spiro[furan-2,3′-indoline]-3-carboxylate derivatives via a...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Vol. 29; no. 6; p. 1223
Main Authors: Khalaj, Mehdi, Zarandi, Maryam, Samadi Kazemi, Malihe, Musavi, Seyed Mahmoud, Hohnsen, Johannes, Klein, Axel
Format: Journal Article
Language:English
Published: Switzerland MDPI AG 01.03.2024
MDPI
Subjects:
Acetic acid
Amino acids
butenolides
Catalysts
Chemical bonds
Furans
Hydrogen
imidazolium hydrogen sulfate
ionic liquid catalyst
Medical equipment and supplies industry
Medical test kit industry
Nanoparticles
Pharmaceutical industry
pyridinium hydrogen sulfate
Solvents
spiro compounds
spiro[furan-2,3′-indoline]-3-carboxylate derivatives
Sulfates
Sulfuric acid
United States
Germany
United States > US
butenolides
spiro[furan-2,3′-indoline]-3-carboxylate derivatives
imidazolium hydrogen sulfate
pyridinium hydrogen sulfate
spiro compounds
ionic liquid catalyst
ISSN:1420-3049, 1420-3049
Online Access:Get full text
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Summary:Two previously described Brønsted acidic ionic liquids, 3,3′-(1,6-hexanediyl)bis(1-methyl)-1H-imidazolium hydrogen sulfate (Cat1) and 1,1′-(1,6-hexanediyl)bis(pyridinium) hydrogen sulfate (Cat2), were used as catalysts for the preparation of spiro[furan-2,3′-indoline]-3-carboxylate derivatives via a three-component reaction of anilines, isatins (N-alkyl-indoline-2,3-diones), and diethyl acetylenedicarboxylate, in high yields. The use of ultrasonic (US) irradiation led to the targeted products (1a–15a) in high yields ranging from 80% to 98%. Under the same conditions, the use of sulfuric acid and acetic acid as a Brønstedt catalyst did not yield the desired benchmark product 1a.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules29061223