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

ABSTRACT: 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.

SUBMITTER: Khalaj M 

PROVIDER: S-EPMC10976190 | biostudies-literature | 2024 Mar

REPOSITORIES: biostudies-literature

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

Khalaj Mehdi M   Zarandi Maryam M   Samadi Kazemi Malihe M   Musavi Seyed Mahmoud SM   Hohnsen Johannes J   Klein Axel A  

Molecules (Basel, Switzerland) 20240308 6

Two previously described Brønsted acidic ionic liquids, 3,3'-(1,6-hexanediyl)bis(1-methyl)-1<i>H</i>-imidazolium hydrogen sulfate (<b>Cat1</b>) and 1,1'-(1,6-hexanediyl)bis(pyridinium) hydrogen sulfate (<b>Cat2</b>), were used as catalysts for the preparation of spiro[furan-2,3'-indoline]-3-carboxylate derivatives via a three-component reaction of anilines, isatins (<i>N</i>-alkyl-indoline-2,3-diones), and diethyl acetylenedicarboxylate, in high yields. The use of ultrasonic (US) irradiation led  ...[more]

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