abstract
The alkylation of a series of nitroindazole derivatives with 1,2-dibromoethane afforded the corresponding N-(2-bromoethyl)- and N-vinyl-nitro-1H-indazoles. The Cu(I)-catalysed azide- alkyne 1,3-dipolar cycloaddition was selected to substitute the nitroindazole core with 1,4-disubstituted triazole units after converting one of the N-(2-bromoethyl)nitroindazoles into the corresponding azide. The reactivity in 1,3-dipolar cycloaddition reactions with nitrile imines generated in situ from ethyl hydrazono-alpha-bromoglyoxylates was studied with nitroindazoles bearing a vinyl unit. The corresponding nitroindazole-pyrazoline derivatives were obtained in good to excellent yields.
keywords
CLICK CHEMISTRY; 1,3-DIPOLAR CYCLOADDITION; HUISGEN CYCLOADDITION; INDAZOLE; DERIVATIVES; COPPER
subject category
Biochemistry & Molecular Biology; Chemistry
authors
Eddahmi, M; Moura, NMM; Bouissane, L; Amiri, O; Faustino, MAF; Cavaleiro, JAS; Mendes, RF; Paz, FAA; Neves, MGPMS; Rakib, E
our authors
Filipe Alexandre Almeida Paz
Principal Researcher
Ricardo Faria Mendes
Junior Researcheracknowledgements
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) through national founds 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 Ref. 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 the 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). APC was sponsored by MDPI.