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- Title
A Suitable Functionalization of Nitroindazoles with Triazolyl and Pyrazolyl Moieties via Cycloaddition Reactions.
- Authors
Eddahmi, Mohammed; Moura, Nuno M. M.; Bouissane, Latifa; Amiri, Ouafa; Faustino, M. Amparo F.; Cavaleiro, José A. S.; Mendes, Ricardo F.; Paz, Filipe A. A.; Neves, Maria G. P. M. S.; Rakib, El Mostapha; McPhee, Derek J.
- 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-α-bromoglyoxylates was studied with nitroindazoles bearing a vinyl unit. The corresponding nitroindazole-pyrazoline derivatives were obtained in good to excellent yields.
- Subjects
RING formation (Chemistry); NITRILIMINES; PYRAZOLYL compounds; ALKYLATION; CLICK chemistry; PYRROLIDINE synthesis
- Publication
Molecules, 2020, Vol 25, Issue 1, p126
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules25010126