Copper-Catalyzed Three-Component Reaction of Alkynes, TMSN₃, and Ethers: Regiocontrollable Synthesis of N¹- and N²-Oxyalkylated 1,2,3-Triazoles

Abstract

A new copper-catalyzed selective synthesis of N 1 -and N 2 -oxyalkylated 1,2,3-triazoles has been developed through a three-component reaction of alkynes, TMSN 3 , and ethers. Through this methodology, a series of N 1 -and N 2oxyalkylated 1,2,3-triazoles could be efficiently and regioselectively obtained from simple and readily available starting materials with favorable functional group tolerance.

Recent developments and perspectives in the copper-catalyzed multicomponent synthesis of heterocycles

“…Copper( i )-catalyzed reaction of alkynes, ethers and TMSN 3 for the preparation of N 1 - and N 2 -oxyalkylated 1,2,3-triazoles was revealed by Wei and co-workers. 25 CuCl was the copper source used and usage of oxidant DTBP (di- tert -butyl peroxide) gave good results in this regioselective protocol ( Scheme 14 ). Optimization of reaction conditions carried out concluded that 5 mol% and 20 mol% were the optimum amount of CuCl required for the synthesis of N 1 -substituted triazoles and N 2 -substituted triazoles respectively.…”

Anchoring Cu nanoparticles on functionalized multi‐walled carbon nanotube for regioselective synthesis of 1,2,3‐triazoles via click reaction

“…The separated catalyst was washed with hot methanol (3 Â 10 mL) and dried in the oven (50 C) to be ready for the next run. The resulting mixture was diluted with distilled water (10 mL) and extracted with EtOAc (3 Â 10 mL), and then, the organic layer was washed with saturated brine and finally dried over anhydrous Na 2 White crystal, m.p. : 128-130 C (Lit.…”

“…A wide range of benefits in medicinal chemistry, [ 1 ] organic chemistry and synthesis as building blocks, [ 2 ] catalysis and material science, [ 3–5 ] polymer science, [ 6 ] bioconjugation, [ 7,8 ] drug discovery, [ 9,10 ] industry, [ 11 ] and agrochemical [ 12 ] are the main reasons of inconsiderable interest to the 1,2,3‐triazole family. According to this extensive utility, development of various synthetic methods is obvious.…”

Synthesis methods of 1,2,3-/1,2,4-triazoles: A review

“…In 2019, Pengli Bao developed a similar reaction condition for selective production of 1,4- and 2,4-disubstitued-1,2,3-triazoles reaction of three-component of alkynes, TMSN 3 , and ethers by copper catalysis ( Bao et al, 2019 ). The target products were obtained in high yield (86%) ( Bao et al, 2019 ) at 80°C using tert-butanol peroxide as an oxidant and ether as a solvent and reactant. In addition, the synthesis of 1,4- and 2,4- disubstitued-1,2,3-triazole could be selectively regulated by changing the amount of cuprous chloride.…”