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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| Format: | Article |
| Published: |
2023
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| Online Access: | https://repository.li.mahidol.ac.th/handle/123456789/84171 |
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| Institution: | Mahidol University |
| Summary: | 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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