New nitroindazolylacetonitriles: efficient synthetic access via vicarious nucleophilic substitution and tautomeric switching mediated by anions

authors	Eddahmi, M; Moura, NMM; Bouissane, L; Gamouh, A; Faustino, MAF; Cavaleiro, JAS; Paz, FAA; Mendes, RF; Lodeiro, C; Santos, SM; Neves, MGPMS; Rakib, E
nationality	International
journal	NEW JOURNAL OF CHEMISTRY
keywords	BIOLOGICAL EVALUATION; ANHYDROUS SNCL2; DERIVATIVES; INDAZOLES; HYDROGEN; REDUCTION; ARYNES; KETO
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 H-1-NMR titrations. The formation of tautomeric species induced by anionic species was endorsed by Density Functional Theory calculations.
publisher	ROYAL SOC CHEMISTRY
issn	1144-0546
isbn	1369-9261
year published	2019
volume	43
issue	36
beginning page	14355
ending page	14367
digital object identifier (doi)	10.1039/c9nj02807b
web of science category	Chemistry, Multidisciplinary
subject category	Chemistry
unique article identifier	WOS:000486223200015