Jatuporn Meesin, Nawasit Chotsaeng, C. Kuhakarn
Mar 1, 2022
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Journal
Synlett
Abstract
A novel dimerization of 3-chlorooxindoles promoted by potassium ethylxanthate to access isoindigo derivatives is described. The reactions readily proceeded at room temperature in a short reaction time. The mechanistic study revealed that 3-chlorooxindole is initially converted to O-ethyl S-(2-oxoindolin-3-yl) carbonodithioate which subsequently undergoes dimerization upon elimination of carbon disulfide. In almost all cases, analytically pure isoindigos were isolated in moderate to good yields without the requirement of chromatographic purification.