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

Boris Letribot (1) , Régis Delatouche (1) , Hervé Rouillard (1) , Antoine Bonnet (1) , Jean-René Chérouvrier (1) , Lisianne Domon (1) , Thierry Besson (2) , Valérie Thiéry (1)

1 LIENSs - LIttoral ENvironnement et Sociétés
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse

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.

Mots clés: 3-alkenyl-2-oxindole; Appel’s salt; 1 2 3-dithiazole

Domaines: Chimie organique; Chimie thérapeutique

Boris Letribot, Régis Delatouche, Hervé Rouillard, Antoine Bonnet, Jean-René Chérouvrier, et al.. Synthesis of 2-Mercapto-(2-Oxoindolin-3-Ylidene)Acetonitriles from 3-(4-Chloro-5H-1,2,3-Dithiazol-5-Ylidene)Indolin-2-ones. Molecules, 2018, 23 (6), pp.1390. ⟨10.3390/molecules23061390⟩. ⟨hal-02197268⟩