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
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
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journal impact factor 3.201
5 year journal impact factor 3.181
category normalized journal impact factor percentile 62.281
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