A Suitable Functionalization of Nitroindazoles with Triazolyl and Pyrazolyl Moieties via Cycloaddition Reactions
authors Eddahmi, M; Moura, NMM; Bouissane, L; Amiri, O; Faustino, MAF; Cavaleiro, JAS; Mendes, RF; Paz, FAA; Neves, MGPMS; Rakib, E
nationality International
journal MOLECULES
author keywords nitrogen heterocycles; nitroindazole; alkylation; click chemistry; 1, 3-dipolar cycloaddition; nitrile imines
keywords CLICK CHEMISTRY; 1,3-DIPOLAR CYCLOADDITION; HUISGEN CYCLOADDITION; INDAZOLE; DERIVATIVES; COPPER
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.
publisher MDPI
year published 2020
volume 25
issue 1
digital object identifier (doi) 10.3390/molecules25010126
web of science category Biochemistry & Molecular Biology; Chemistry, Multidisciplinary
subject category Biochemistry & Molecular Biology; Chemistry
unique article identifier WOS:000513770000126
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