Synthesis of 2-Mercapto-(2-Oxoindolin-3-Ylidene)Acetonitriles from 3-(4-Chloro-5H-1,2,3-Dithiazol-5-Ylidene)Indolin-2-ones
by
Boris Letribot 1, Régis Delatouche 1, Hervé Rouillard 1, Antoine Bonnet 1, Jean-René Chérouvrier 1, Lisianne Domon 1, Thierry Besson 2
and Valérie Thiéry 1,*
and Valérie Thiéry 1,*
1
University of La Rochelle, UMR CNRS 7266 LIENSs, 17000 La Rochelle, France
2
Normandie University, UNIROUEN, INSA Rouen, CNRS, COBRA UMR 6014, 76000 Rouen, France
*
Author to whom correspondence should be addressed.
Molecules 2018, 23(6), 1390; https://doi.org/10.3390/molecules23061390
Received: 23 May 2018 / Revised: 4 June 2018 / Accepted: 6 June 2018 / Published: 8 June 2018
(This article belongs to the Special Issue Focusing on Sulfur in Medicinal Chemistry)
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.
View Full-Text
Keywords:
1,2,3-dithiazole; Appel’s salt; 3-alkenyl-2-oxindole
▼
Show Figures
Graphical abstract
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited
MDPI and ACS Style
Letribot, B.; Delatouche, R.; Rouillard, H.; Bonnet, A.; Chérouvrier, J.-R.; Domon, L.; Besson, T.; Thiéry, V. 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, 1390.
Show more citation formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.
