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.841712023-06-18T23:57:55Z Dimerization of 3-Chlorooxindoles Mediated by Potassium Ethylxanthate: Synthesis of Isoindigos Meesin J. 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 arbon disulfide. In almost all cases, analytically pure isoindigos were isolated in moderate to good yields without a requirement for chromatographic purification. 2023-06-18T16:57:55Z 2023-06-18T16:57:55Z 2022-09-01 Article Synlett Vol.33 No.14 (2022) , 1317-1322 10.1055/a-1784-2304 14372096 09365214 2-s2.0-85127378157 https://repository.li.mahidol.ac.th/handle/123456789/84171 SCOPUS |
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Chemistry Meesin J. 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 arbon 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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Mahidol University |
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Mahidol University Meesin J. |
| format |
Article |
| author |
Meesin J. |
| author_sort |
Meesin J. |
| 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 |
2023 |
| url |
https://repository.li.mahidol.ac.th/handle/123456789/84171 |
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1781415564036538368 |