New nitroindazolylacetonitriles: efficient synthetic access via vicarious nucleophilic substitution and tautomeric switching mediated by anions. (27th August 2019)

• Record Type: Journal Article
• Authors: Eddahmi, Mohammed; Moura, Nuno M. M.; Bouissane, Latifa; Gamouh, Ahmed; Faustino, Maria A. F.; Cavaleiro, José A. S.; Paz, Filipe A. A.; Mendes, Ricardo F.; Lodeiro, Carlos; Santos, Sérgio M.; Neves, Maria G. P. M. S.; Rakib, El Mostapha
• Is Part Of: New journal of chemistry. Volume 43:Number 36(2019)
• Page Start: 14355
• Page End: 14367
• Publication Date: 2019-08-27
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/c9nj02807b
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : Efficient synthesis of new N -methylnitroindazolylacetonitriles and their ability to switch between tautomeric forms in the presence of anionic species. Abstract : New N -alkyl-nitroindazolylacetonitriles were efficiently obtained via vicarious nucleophilic substitution of N -methyl-nitroindazoles with 4-chlorophenoxyacetonitrile. All compounds were fully characterized by NMR and mass spectroscopy techniques and the structures of some of them were additionally confirmed by X-ray diffraction analysis data. Tautomeric switching was observed in this series of nitroindazolylacetonitriles upon addition of basic anions followed by UV-Vis spectrophotometric and 1 H-NMR titrations. The formation of tautomeric species induced by anionic species was endorsed by Density Functional Theory calculations.