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Article

A Suitable Functionalization of Nitroindazoles with Triazolyl and Pyrazolyl Moieties via Cycloaddition Reactions

1
Laboratory of Organic and Analytic Chemistry, Faculty of Sciences and Technics, Sultan Moulay Slimane University, BP 523, 2300 Beni-Mellal, Morocco
2
QOPNA & LAQV-REQUIMTE, Chemistry Department, University of Aveiro, 3810-193 Aveiro, Portugal
3
CICECO - Aveiro Institute of Materials, Chemistry Department, University of Aveiro, 3810-193 Aveiro, Portugal
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Molecules 2020, 25(1), 126; https://doi.org/10.3390/molecules25010126
Received: 23 November 2019 / Revised: 16 December 2019 / Accepted: 26 December 2019 / Published: 28 December 2019
(This article belongs to the Collection Heterocyclic Compounds)
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. View Full-Text
Keywords: nitrogen heterocycles; nitroindazole; alkylation; click chemistry; 1,3-dipolar cycloaddition; nitrile imines nitrogen heterocycles; nitroindazole; alkylation; click chemistry; 1,3-dipolar cycloaddition; nitrile imines
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MDPI and ACS Style

Eddahmi, M.; Moura, N.M.M.; Bouissane, L.; Amiri, O.; Faustino, M.A.F.; Cavaleiro, J.A.S.; Mendes, R.F.; Paz, F.A.A.; Neves, M.G.P.M.S.; Rakib, E.M. A Suitable Functionalization of Nitroindazoles with Triazolyl and Pyrazolyl Moieties via Cycloaddition Reactions. Molecules 2020, 25, 126. https://doi.org/10.3390/molecules25010126

AMA Style

Eddahmi M, Moura NMM, Bouissane L, Amiri O, Faustino MAF, Cavaleiro JAS, Mendes RF, Paz FAA, Neves MGPMS, Rakib EM. A Suitable Functionalization of Nitroindazoles with Triazolyl and Pyrazolyl Moieties via Cycloaddition Reactions. Molecules. 2020; 25(1):126. https://doi.org/10.3390/molecules25010126

Chicago/Turabian Style

Eddahmi, Mohammed, Nuno M. M. Moura, Latifa Bouissane, Ouafa Amiri, M. Amparo F. Faustino, José A. S. Cavaleiro, Ricardo F. Mendes, Filipe A. A. Paz, Maria G. P. M. S. Neves, and El Mostapha Rakib. 2020. "A Suitable Functionalization of Nitroindazoles with Triazolyl and Pyrazolyl Moieties via Cycloaddition Reactions" Molecules 25, no. 1: 126. https://doi.org/10.3390/molecules25010126

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