Synthesis of bi- and bis-1,2,3-triazoles by copper-catalyzed Huisgen cycloaddition: A family of valuable products by click chemistry

Abstract

SummaryThe Cu(I)-catalyzed azide-alkyne cycloaddition reaction, also known as click chemistry, has become a useful tool for the facile formation of 1,2,3-triazoles. Specifically, the utility of this reaction has been demonstrated by the synthesis of structurally diverse bi- and bis-1,2,3-triazoles. The present review focuses on the synthesis of such bi- and bistriazoles and the importance of using copper-promoted click chemistry (CuAAC) for such transformations. In addition, the application of bitriazoles and the related CuAAAC reaction in different fields, including medicinal chemistry, coordination chemistry, biochemistry, and supramolecular chemistry, have been highlighted.

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

“…These two adducts were easily separated by column chromatography using hexane-ethyl acetate as solvent (Scheme 3). The structure of all the newly synthesised compounds were unambiguously confirmed by using 1D ( 1 H and 13 In this series of compounds, the success of the reaction was easily confirmed from the 1 H-NMR spectra analysis. It shows the resonance of the protons from the ethylenic bridge as two multiplets at δ 5.10-5.01 ppm and δ 5.00-4.92 ppm and a remarkable singlet in the aromatic region due to the resonance of the proton from the triazole ring.…”

“…These two adducts were easily separated by column chromatography using hexane-ethyl acetate as solvent (Scheme 3). The structure of all the newly synthesised compounds were unambiguously confirmed by using 1D ( 1 H and 13 In this series of compounds, the success of the reaction was easily confirmed from the 1 H-NMR The structure of all the newly synthesised compounds were unambiguously confirmed by using 1D ( 1 H and 13 C spectra) and 2D [( 1 H, 1 H) COSY, ( 1 H, 13…”

“…For the incorporation of triazole units in the nitroindazole core (Scheme 2) it was selected the N-bromoethylnitroindazole 2b that was efficiently converted into the required 5-nitroindazole azide 6 (88%) by reaction with an excess of sodium azide in DMF. The structure of this synthon was confirmed by mass spectrometry and 1 H-NMR and 13 by the presence of electron donor groups instead of electron-withdrawing groups in the para position of the phenyl ring from the alkyne reagent. The excellent performance of 6 in this CuAAC reactions prompted us to extend our study to 1,3diethynylbenzene (Scheme 3).…”

“…An attractive approach giving rise to substituted triazole derivatives is based on the 1,3-dipolar cycloaddition of azides to terminal alkynes catalysed by copper(I), the so-called Copper(I)-catalysed azide-alkyne (CuAAC) reaction [10][11][12]. In this click chemistry approach the presence of copper(I) is a crucial requirement to afford selectively only one of the regioisomers -the 1,4-disubstituted 1,2,3-triazole [11,13,14].…”

An Efficient Approach for the Synthesis of 1,2,3‐Triazole Moiety to Generate Uracil Molecular Architectures Through Cu‐Catalyzed Azide–Alkyne Cycloaddition

“…The design and synthesis of dendritic architectures through the click chemistry approach have been gaining great attention during the recent years . Click chemistry refers to Cu(I)‐catalyzed Huisgen 1,3‐dipolar cycloaddition of azide and alkyne to obtain 1,4‐disubstitued 1,2,3‐triazole under mild reaction conditions with excellent chemoselectivity and good yield .…”