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


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.



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Eddahmi, M; Moura, NMM; Bouissane, L; Gamouh, A; Faustino, MAF; Cavaleiro, JAS; Paz, FAA; Mendes, RF; Lodeiro, C; Santos, SM; Neves, MGPMS; Rakib, E

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Thanks are due to the University of Aveiro and FCT/MCT for the financial support for the QOPNA research Unit (FCT UID/QUI/00062/2019) and Associate Laboratory Research Unit for Green Chemistry - Clean Processes and Technologies - LAQV (FCT/MEC UID/QUI/50006/2013 and POCI-01-0145-FEDER - 007265) through national funds and, where applicable, co-financed by the FEDER, within the PT2020 Partnership Agreement, and to the Portuguese NMR Network. The authors also thank CICECO-Aveiro Institute of Materials (FCT UID/CTM/50011/2019), Sultan Moulay Slimane University and the Transnational cooperation programs, FCT-CNRST (Morocco), for financial assistance (2019-2020). NMM Moura thanks his research contract (CDL-CTTRI-88-89-97-ARH/2018) which is funded by national funds (OE), through FCT - Fundacao para a Ciencia e a Tecnologia, I.P., in the scope of the framework contract foreseen in numbers 4, 5 and 6 of article 23, of the Law Decree 57/2016, of August 29, changed by Law 57/2017, of July 19. RF Mendes gratefully acknowledges FCT for a Junior Research Position (CEECIND/00553/2017).

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