One-pot synthesis of 4,5-disubstituted 1,2,3-(NH)-triazoles by silica supported-zinc bromide in the aerobic condition

Abstract

An efficient one-pot cross-coupling/1,3-dipolar cycloaddition sequence was developed for a convenient synthesis of 4,5-disubstituted-1,2,3-(NH)-triazoles, starting from various acid chlorides, terminal alkynes and sodium azide in the presence of silica supported-zinc bromide under aerobic conditions.

Recent progress in the synthesis of azoles and related five‐membered ring heterocycles using silica‐supported heterogeneous catalysts

“…The reaction was carried out under anhydrous conditions at room temperature followed by the addition of sodium azide in CH 3 CN/H 2 O (3:1) by heating at 50 C for another 3 h to give 4,5-disubstituted 1,2,3-(NH)-triazoles. The synthesis of substituted triazole derivatives without using palladium or copper metal is one of the significant features of this synthetic method (Scheme 8) [24].…”

Aminoazole-Based Diversity-Oriented Synthesis of Heterocycles

“…Another multicomponent approach (Figure 26 ) included consecutive reaction of terminal alkyne 183 with acyl halide 311 , and then with sodium azide with application of zinc bromide, which served as a catalyst for both steps of the process (Keivanloo et al, 2013 ).…”

An SiO2/ZnBr2mediated expeditious approach to 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one derivatives in water under microwave irradiation

“…Keivanloo et al exploited SiO 2 /ZnBr 2 for the synthesis of ynones 31 by cross-coupling of acid chloride with terminal alkynes and synthesis of 4,5-disubstituted 1,2,3-(NH)-triazoles. 32 Moreover, Kodomari and co-workers 33 also reported the synthesis of triarylmethanes and 9,10-diarylanthracenes and Clark et al 34 reported bromination of aromatic substrate using SiO 2 /ZnBr 2 catalyst. The catalyst possesses inherent environmentally benevolent properties such as non-toxicity, biocompatibility, physiological inertness, recyclability, inexpensiveness and thermal stability.…”