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<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 s...
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| Format: | Article |
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MDPI AG
2024-03-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/29/6/1223 |
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| author | Mehdi Khalaj Maryam Zarandi Malihe Samadi Kazemi Seyed Mahmoud Musavi Johannes Hohnsen Axel Klein |
| author_facet | Mehdi Khalaj Maryam Zarandi Malihe Samadi Kazemi Seyed Mahmoud Musavi Johannes Hohnsen Axel Klein |
| author_sort | Mehdi Khalaj |
| collection | DOAJ |
| description | 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 to the targeted products (<b>1a</b>–<b>15a</b>) 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 <b>1a</b>. |
| first_indexed | 2024-04-24T17:58:23Z |
| format | Article |
| id | doaj.art-7ab6eadd4bb24008a5328b1c2999bf4a |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-24T17:58:23Z |
| publishDate | 2024-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-7ab6eadd4bb24008a5328b1c2999bf4a2024-03-27T13:56:46ZengMDPI AGMolecules1420-30492024-03-01296122310.3390/molecules29061223Multi-Component Syntheses of Spiro[furan-2,3′-indoline]-3-carboxylate Derivatives Using Ionic Liquid CatalystsMehdi Khalaj0Maryam Zarandi1Malihe Samadi Kazemi2Seyed Mahmoud Musavi3Johannes Hohnsen4Axel Klein5Department of Chemistry, Buinzahra Branch, Islamic Azad University, Buinzahra 1477893855, IranDepartment of Chemistry, Buinzahra Branch, Islamic Azad University, Buinzahra 1477893855, IranDepartment of Chemistry, Faculty of Science, Bojnourd Branch, Islamic Azad University, Bojnourd 9417697796, IranDepartment of Chemistry, Buinzahra Branch, Islamic Azad University, Buinzahra 1477893855, IranFaculty of Mathematics and Natural Sciences, Department of Chemistry and Biochemistry, Institute for Inorganic Chemistry, University of Cologne, Greinstrasse 6, D-50939 Köln, GermanyFaculty of Mathematics and Natural Sciences, Department of Chemistry and Biochemistry, Institute for Inorganic Chemistry, University of Cologne, Greinstrasse 6, D-50939 Köln, GermanyTwo 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 to the targeted products (<b>1a</b>–<b>15a</b>) 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 <b>1a</b>.https://www.mdpi.com/1420-3049/29/6/1223spiro[furan-2,3′-indoline]-3-carboxylate derivativesionic liquid catalystbutenolidesspiro compoundsimidazolium hydrogen sulfatepyridinium hydrogen sulfate |
| spellingShingle | Mehdi Khalaj Maryam Zarandi Malihe Samadi Kazemi Seyed Mahmoud Musavi Johannes Hohnsen Axel Klein Multi-Component Syntheses of Spiro[furan-2,3′-indoline]-3-carboxylate Derivatives Using Ionic Liquid Catalysts Molecules spiro[furan-2,3′-indoline]-3-carboxylate derivatives ionic liquid catalyst butenolides spiro compounds imidazolium hydrogen sulfate pyridinium hydrogen sulfate |
| title | Multi-Component Syntheses of Spiro[furan-2,3′-indoline]-3-carboxylate Derivatives Using Ionic Liquid Catalysts |
| title_full | Multi-Component Syntheses of Spiro[furan-2,3′-indoline]-3-carboxylate Derivatives Using Ionic Liquid Catalysts |
| title_fullStr | Multi-Component Syntheses of Spiro[furan-2,3′-indoline]-3-carboxylate Derivatives Using Ionic Liquid Catalysts |
| title_full_unstemmed | Multi-Component Syntheses of Spiro[furan-2,3′-indoline]-3-carboxylate Derivatives Using Ionic Liquid Catalysts |
| title_short | Multi-Component Syntheses of Spiro[furan-2,3′-indoline]-3-carboxylate Derivatives Using Ionic Liquid Catalysts |
| title_sort | multi component syntheses of spiro furan 2 3 indoline 3 carboxylate derivatives using ionic liquid catalysts |
| topic | spiro[furan-2,3′-indoline]-3-carboxylate derivatives ionic liquid catalyst butenolides spiro compounds imidazolium hydrogen sulfate pyridinium hydrogen sulfate |
| url | https://www.mdpi.com/1420-3049/29/6/1223 |
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