A facile and regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles using click chemistry

Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from Aromatic a-Bromoketones, Sodium Azide and Terminal Acetylenes via Cu/Cu(OTf)2-catalyzed Click Reaction under Microwave Irradiation

“…Because H 2 O can be used as a solvent under microwave irradiation, we can claim that this one-pot, three-component protocol has all qualities and superiorities expected from click chemistry, which was first fully described by Sharpless et al in 2001 [25]. In comparison with other methods which needed long reaction times (8 -12 h) [11,12] and gave moderate yields (61 -86 %) [11,13], this method is completed in about one to three hours giving good yields of products (72 -92 %) under the conventional method and in 8 -14 minutes giving excellent yields of products (85 -95 %) under microvawe irradiation. The pure products are obtained by simple filtration.…”

Synthesis of a Novel Rhizobitoxine-Like Triazole-Containing Amino Acid

“…1,2,3-Triazole derivatives have gained a recent interest in medicinal chemistry because they are pharmacophores with good stability and high aqueous solubility, [17][18][19][20][21] particularly in the area of peptidomimetics 22 and are readily accessible by the Huisgen 1,3-dipolar cycloaddition involving an alkyne and an azide. [23][24][25][26] In this paper, we describe the synthesis of a new triazole-containing amino acid analogue of rhizobitoxine in protected form (compound (1S,2S)-2) from serine ( Figure 2) where the central enol ether linkage in rhizobitoxine is replaced by the robust 1,2,3-triazole linker in such a way that there is no longer β,γ-unsaturation to the amino acid moiety. This analogue should be a stable analogue compared to unstable vinylglycine derivatives and, based on reported mechanisms of inhibition, such an unusual amino acid could be a potential inhibitor of PLP-dependent enzymes.…”

Regioselective synthesis of 1,2,3-triazoles catalyzed over ZnO supported copper oxide nanocatalyst as a new and efficient recyclable catalyst in water

“…2 These compounds are useful building blocks in the chemistry, resistant to moisture, oxygen, light, and also metabolism in the body. 3 In addition, 1,2,3-triazoles are used as dyes, corrosion inhibition agents, photostabilizers, and photographic materials. 4 The main method for the synthesis of 1,2,3-triazoles is the Huisgen 1,3-dipolar cycloaddition reaction of azides with alkynes.…”