Dimerization of 3-Chlorooxindoles Mediated by Potassium Ethylxanthate: Synthesis of Isoindigos
A novel dimerization of 3-chlorooxindoles promoted by potassium ethylxanthate to access isoindigo derivatives is described. The reactions proceeded readily at room temperature in short reaction times. A mechanistic study revealed that the 3-chlorooxindole is initially converted into O-ethyl S-(2-oxo...
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th-mahidol.737202022-08-04T10:52:47Z Dimerization of 3-Chlorooxindoles Mediated by Potassium Ethylxanthate: Synthesis of Isoindigos Jatuporn Meesin Nawasit Chotsaeng Chutima Kuhakarn King Mongkuts University of Technology Mahidol University Chemistry A novel dimerization of 3-chlorooxindoles promoted by potassium ethylxanthate to access isoindigo derivatives is described. The reactions proceeded readily at room temperature in short reaction times. A mechanistic study revealed that the 3-chlorooxindole is initially converted into O-ethyl S-(2-oxo-2,3-dihydro-1H-indol-3-yl) dithiocarbonate, which subsequently undergoes dimerization with elimination of carbon disulfide. In almost all cases, analytically pure isoindigos were isolated in moderate to good yields without a requirement for chromatographic purification. 2022-08-04T03:52:47Z 2022-08-04T03:52:47Z 2022-01-01 Article Synlett. (2022) 10.1055/a-1784-2304 14372096 09365214 2-s2.0-85127378157 https://repository.li.mahidol.ac.th/handle/123456789/73720 Mahidol University SCOPUS https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85127378157&origin=inward |
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Chemistry Jatuporn Meesin Nawasit Chotsaeng Chutima Kuhakarn Dimerization of 3-Chlorooxindoles Mediated by Potassium Ethylxanthate: Synthesis of Isoindigos |
| description |
A novel dimerization of 3-chlorooxindoles promoted by potassium ethylxanthate to access isoindigo derivatives is described. The reactions proceeded readily at room temperature in short reaction times. A mechanistic study revealed that the 3-chlorooxindole is initially converted into O-ethyl S-(2-oxo-2,3-dihydro-1H-indol-3-yl) dithiocarbonate, which subsequently undergoes dimerization with elimination of carbon disulfide. In almost all cases, analytically pure isoindigos were isolated in moderate to good yields without a requirement for chromatographic purification. |
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King Mongkuts University of Technology |
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King Mongkuts University of Technology Jatuporn Meesin Nawasit Chotsaeng Chutima Kuhakarn |
| format |
Article |
| author |
Jatuporn Meesin Nawasit Chotsaeng Chutima Kuhakarn |
| author_sort |
Jatuporn Meesin |
| title |
Dimerization of 3-Chlorooxindoles Mediated by Potassium Ethylxanthate: Synthesis of Isoindigos |
| title_short |
Dimerization of 3-Chlorooxindoles Mediated by Potassium Ethylxanthate: Synthesis of Isoindigos |
| title_full |
Dimerization of 3-Chlorooxindoles Mediated by Potassium Ethylxanthate: Synthesis of Isoindigos |
| title_fullStr |
Dimerization of 3-Chlorooxindoles Mediated by Potassium Ethylxanthate: Synthesis of Isoindigos |
| title_full_unstemmed |
Dimerization of 3-Chlorooxindoles Mediated by Potassium Ethylxanthate: Synthesis of Isoindigos |
| title_sort |
dimerization of 3-chlorooxindoles mediated by potassium ethylxanthate: synthesis of isoindigos |
| publishDate |
2022 |
| url |
https://repository.li.mahidol.ac.th/handle/123456789/73720 |
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1763488338777473024 |