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)-1 -imidazolium hydrogen sulfate ( ) and 1,1'-(1,6-hexanediyl)bis(pyridinium) hydrogen sulfate ( ), were used as catalysts for the preparation of spiro[furan-2,3'-indoline]-3-carboxylate derivati...

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Veröffentlicht in:Molecules (Basel, Switzerland) Switzerland), 2024-03, Vol.29 (6), p.1223
Hauptverfasser: Khalaj, Mehdi, Zarandi, Maryam, Samadi Kazemi, Malihe, Musavi, Seyed Mahmoud, Hohnsen, Johannes, Klein, Axel
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Sprache:eng
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Zusammenfassung:Two previously described Brønsted acidic ionic liquids, 3,3'-(1,6-hexanediyl)bis(1-methyl)-1 -imidazolium hydrogen sulfate ( ) and 1,1'-(1,6-hexanediyl)bis(pyridinium) hydrogen sulfate ( ), were used as catalysts for the preparation of spiro[furan-2,3'-indoline]-3-carboxylate derivatives via a three-component reaction of anilines, isatins ( -alkyl-indoline-2,3-diones), and diethyl acetylenedicarboxylate, in high yields. The use of ultrasonic (US) irradiation led to the targeted products ( - ) 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 .
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules29061223