Dimerization of 3-Chlorooxindoles Mediated by Potassium Ethyl­xanthate: Synthesis of Isoindigos

Author:

Meesin Jatuporn1ORCID,Chotsaeng Nawasit1,Kuhakarn Chutima2ORCID

Affiliation:

1. Department of Chemistry, School of Science, King Mongkut’s Institute of Technology Ladkrabang

2. Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University

Abstract

AbstractA 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.

Funder

King Mongkut’s Institute of Technology Ladkrabang

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

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