A tunable route to oxidative and eliminative [3+2] cycloadditions of organic azides with nitroolefins: CuO nanoparticles catalyzed synthesis of 1,2,3-triazoles under solvent-free condition

Synthesis of 1,5-Functionalized 1,2,3-Triazoles Using Ionic Liquid/Iron(III) Chloride as Efficient and Reusable Homogeneous Catalyst

“…The azide-olefin cycloaddition furnishes triazoline, an unstable compound that readily decompose but that may be transformed into the stable triazole by eliminative azide olefin cycloaddition (EAOC). In 2 of 13 this process, the olefin carrying a leaving group reacts with the azide to form the intermediate triazoline that gives the corresponding triazole by elimination reaction [14]. Nitroolefins, as versatile starting materials, are excellent dipolarophiles to synthesize triazoles by EAOC cycloaddition.…”

1,5‐Disubstituted‐1,2,3‐triazoles as inhibitors of the mitochondrial Ca2+‐activated F1FO‐ATP(hydrol)ase and the permeability transition pore

“…Although various synthetic procedures to regioselectively produce 1,4‐ and 1,5‐disubstituted triazoles are described in the literature, 42–44 in this paper, we chose to prepare 1,5‐disubstituted‐1,2,3‐triazoles because of their larger dipolar moment than 1,4‐disubstituted triazoles (5.06 versus 4.31 debyes, respectively). Accordingly, most likely the inhibition of an enzyme may be affected by dipole–dipole interactions and strong hydrogen bonds with the employed substrate (Fig.…”

Nanoparticle‐Catalysed 1,3‐Dipolar Cycloadditions

“…Computational modelling of 21 allowed to investigate the correlation between its conformation and bioactivity against the breast cancer cell line MCF-7. [74] Switching the attention to the +2 oxidation state of copper in the absence of reducing agents, it has been reported that the oxidative cycloadditions between azides and activated ethylenes, namely acrolein, methyl vinyl ketone, chalcones [75] and nitro olefins, [76] were feasible in the presence of unsupported suspended CuO nanoparticles. After the optimisation of both the solvent and the catalytic species, starting from a set of ten azides and 22 olefins, 40 examples of 1,4-disubstituted-1,2,3triazoles were obtained with 40-99 % yield (Scheme 13).…”