4,5-Dichloro-1,2,3-dithiazol-1-ium Chloride

Foucourt, Alicia; Chosson, Elizabeth; Besson, Thierry

doi:10.1002/047084289x.rn01113

Cited by 1 publication

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“…Few 3-(thiazol-5-ylidene)indoline-2-one derivatives ( Figure 1 , I ) were reported in the literature [ 26 , 27 ]. To access the required 2-oxoindolylacetonitrile derivatives ( Figure 1 , III ), we decided to explore a new route based on the use of 4,5-dichloro-1,2,3-dithiazolium chloride (Appel’s salt; Scheme 1 , 1 ) [ 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 ]. We planned on functionalizing the oxindole at the C3 position using Appel’s salt and commercially available oxindoles, and then, on studying the ring opening of original 3-(4-chloro-5 H -1,2,3-dithiazol-5-ylidene)indolin-2-one ( Figure 1 , II ) intermediates with various bases, such as sodium hydride and methyl magnesium bromide, or with triphenylphosphine as a nucleophile.…”

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confidence: 99%

Synthesis of 2-Mercapto-(2-Oxoindolin-3-Ylidene)Acetonitriles from 3-(4-Chloro-5H-1,2,3-Dithiazol-5-Ylidene)Indolin-2-ones

et al. 2018

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Alkylidene oxindoles are important functional moieties and building blocks in pharmaceutical and synthetic chemistry. Our interest in biologically active compounds focused our studies on the synthesis of novel oxindoles, bearing on the exocyclic double bond at the C8, CN, and S groups. Extending the potential applications of Appel’s salt, we developed a new synthetic approach by investigating the reactions of C5-substituted 2-oxindoles with 4,5-dichloro-1,2,3-dithiazolium chloride (Appel’s salt) to give original (Z)-3-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)indolin-2-one derivatives, and new 2-mercapto-(2-oxoindolin-3-ylidene)acetonitriles via a dithiazole ring-opening reaction. The work described in this article represents further applications of Appel’s salt in the conception of novel heterocyclic rings, in an effort to access original bioactive compounds. Fifteen new compounds were prepared and fully characterized.

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