A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles

Abstract

Diverse strategies for the efficient and attractive synthesis of a wide variety of relevant 1,4,5-trisubstituted 1,2,3-triazole molecules are reported. The synthesis of this category of diverse fully functionalized 1,2,3-triazoles has become a necessary and unique research subject in modern synthetic organic key transformations in academia, pharmacy, and industry. The current review aims to cover a wide literature survey of numerous synthetic strategies. Recent reports (2017–2021) in the field of 1,4,5-trisubstituted 1,2,3-triazoles are emphasized in this current review.

Selective Synthesis of 5‐Alkynyl Trisubstituted 1,2,3‐triazoles from Azides and Alkynes via Photoexcited Copper(I)acetylides

“…[10][11][12] In particular, the 5-alkynyl trisubstituted 1,2,3-triazoles have attracted much as to the alkyne moiety could be easily transformed into other functional groups [13] and various heterocycles, which improve the biological activity. [14,15] In general, a two-step synthesis of 5-alkynyl trisubstituted 1,2,3-triazoles was reported by Cu/Pd catalyzed multicomponent reaction (MC) 2 R [16] of terminal alkynes, azides via stable 5-iodo-1,2,3-triazoles with prefunctionalized alkynes. [17] Otherwise, a one pot synthesis of 5-alkynyl trisubstituted 1,2,3-triazole was reported by multicomponent reaction of terminal alkyne, azide via oxidative coupling of in-situ formed cuprate-triazole with another equivalent of alkyne.…”

Regioselective Synthesis of 1,4,5‐Trisubstituted 1,2,3‐Triazole Derivatives from α,β‐Unsaturated Carbonyls

“…In the case of bis-triazole substituted analogues (18-24), the six protons of the terminal methyl group appeared at around ~δ 0.86 ppm and four protons of two À NCH 2 À moieties appeared at ~δ 4.0 ppm as triplet confirming the presence of an aliphatic chain of bis-triazole derivatives. On the other hand, for the mono derivatives (13)(14)(15)(16)(17), three protons of the terminal methyl group and two protons of À NCH 2 group appeared in the similar region as of bis triazole, along with the two olefinic protons. In the 13 C NMR spectrum for all aliphatic analogues, the characteristics peaks for aliphatic carbons are observed at ~δ 48.0 ppm for À CH 2 À carbon nearest to À NCH 2 À of triazole ring; the peaks at ~δ 14.0 ppm are found for terminal alkyl group.…”

“…Few trisubstituted 1,2,3‐triazole‐containing compounds are shown in Figure 1 [16] . Recently, the synthesis and applications of 1,4,5‐trisubstituted 1,2,3‐triazoles have received much attention [17–19] . One of the highly versatile and powerful tools for the construction of triazole is the 1,3‐dipolar cycloaddition reactions of alkyne with azide as developed by Huisgen [20] .…”

“…[16] Recently, the synthesis and applications of 1,4,5trisubstituted 1,2,3-triazoles have received much attention. [17][18][19] One of the highly versatile and powerful tools for the construction of triazole is the 1,3-dipolar cycloaddition reactions of alkyne with azide as developed by Huisgen. [20] The synthesis of 1,4,5-trisubstituted 1,2,3-triazoles [21] compared to their 1,4disubstituted 1,2,3-triazoles analogues with regioselectivity was less explored.…”

2-(Nitroaryl)-5-Substituted-1,3,4-Thiadiazole Derivatives with Antiprotozoal Activities: In Vitro and In Vivo Study

“…Natural and synthetic heterocyclic compounds, particularly the azole heterocycles, showed antiprotozoal activity [ 15 , 16 ]. Due to the straightforward synthetic approaches and easy ring functionalization, such scaffolds attract attention in the design of trypanocidal agents [ 17 , 18 ]. Antifungal azoles, such as posaconazole and ravuconazole, were repositioned as potential anti-trypanosomal agents in recent years.…”