35224-98-7Relevant academic research and scientific papers
Cu-Catalyzed Site-Selective and Enantioselective Ring Opening of Cyclic Diaryliodoniums with 1,2,3-Triazoles
Chao, Zengyin,Ma, Mingming,Gu, Zhenhua
, p. 6441 - 6446 (2020)
A Cu-catalyzed enantioselective ring-opening/triazolylation reaction is reported. The reaction shows excellent chemoselectivity regarding the three different nitrogen atoms of 1,2,3-triazoles. The optically enriched axially chiral aryl iodides thus obtained were readily derivatized to different types of chiral phosphine ligands and their corresponding copper or palladium complexes.
Cycloaddition of: N -sulfonyl and N -sulfamoyl azides with alkynes in aqueous media for the selective synthesis of 1,2,3-triazoles
Prasanth, Thumpati,Chakraborti, Gargi,Mandal, Tirtha,Ravichandiran, Velayutham,Dash, Jyotirmayee
supporting information, p. 911 - 915 (2022/02/02)
The cycloaddition of N-sulfonyl and N-sulfamoyl azides with terminal alkynes generally produces amide derivatives via ketenimine intermediates. We herein delineate a Cu(i) catalyzed method using a prolinamide ligand that selectively generates N-sulfonyl a
A [3+2] cycloaddition-1,2-acyl migration-hydrolysis cascade for regioselective synthesis of 1,2,3-triazoles in water
Chakraborti, Gargi,Dash, Jyotirmayee,Mandal, Tirtha,Roy, Charles Patriot
supporting information, p. 7970 - 7973 (2021/08/17)
A cascade sequence involving [3+2] cycloaddition, 1,2-acyl migration and hydrolysis produces 2H-1,2,3-triazolesviathe regioselective formation ofN2-carboxyalkylated triazoles. The reaction proceeds in aqueous media through intriguing reaction kinetics using a CuI-prolinamide catalyst system. Prolinamide promotes the novel organocatalytic 1,2-acyl migration as well as hydrolysis of the resultingN2-carboxyalkylated triazoles.
Direct Synthesis of 4-Aryl-1,2,3-triazoles via I2-Promoted Cyclization under Metal- And Azide-Free Conditions
Geng, Xiao,Huang, Chun,Wang, Li-Sheng,Wu, An-Xin,Wu, Yan-Dong,Yu, Xiao-Xiao,Zhao, Peng,Zhou, You
, p. 13664 - 13672 (2021/10/01)
We herein report an iodine-mediated formal [2 + 2 + 1] cyclization of methyl ketones, p-toluenesulfonyl hydrazines, and 1-aminopyridinium iodide for preparation of 4-aryl-NH-1,2,3-triazoles under metal- and azide-free conditions. Notably, this is achieved
Access to (Z)-β-Substituted Enamides from N1-H-1,2,3-Triazoles
Wang, Tao,Tang, Zongyuan,Luo, Han,Tian, Yi,Xu, Mingchuan,Lu, Qixing,Li, Baosheng
supporting information, p. 6293 - 6298 (2021/08/23)
A direct ring-opening/nucleophilic substitution reaction of N1-H-1,2,3-triazoles has been described. Divergent (Z)-β-halogen- or sulfonyl-substituted enamides could be stereospecifically synthesized in a tunable manner. This strategy might not only enable
Silica immobilized copper N-heterocyclic carbene: An effective route to 1,2,3-triazoles via azide-alkyne cycloaddition and multicomponent click reaction
Garg, Anirban,Borah, Nobomi,Sultana, Jasmin,Kulshrestha, Akshay,Kumar, Arvind,Sarma, Diganta
, (2021/06/11)
A new silica supported copper N-heterocyclic carbene (Cu-NHC@SiO2) complex is prepared and characterized by scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX) and X-ray photoelectron spectroscopy (XPS) analyses. This complex is an efficient and easily retrievable catalyst for 1,2,3-triazole synthesis through direct azide-alkyne cycloaddition reaction as well as one-pot reaction using arylboronic acids. This catalytic system is also suitable for synthesis of 4-aryl-NH-1,2,3-triazoles from diverse benzaldehydes. Further, the catalyst can efficiently be recycled up to fifth cycle for all the three methods of 1,2,3-triazole synthesis through direct azide-alkyne cycloaddition and multi-component reactions.
Magnetically separable ZnFe2O4 nanoparticles: A low cost and sustainable catalyst for propargyl amine and NH-triazole synthesis
Bordoloi, Ankur,Chetia, Swadhin,Garg, Anirban,Guha, Ankur Kanti,Hazarika, Roktopol,Kalita, Amlan Jyoti,Kulshrestha, Akshay,Kumar, Arvind,Phukan, Parmita,Sarma, Diganta
, (2021/09/14)
The multicomponent reaction (MCR) strategy for the construction of important molecular scaffolds is in trending nowadays and among them, A3-coupling stands in a significant position. Aldehyde, amine and alkynes are coupled in this particular reaction via C-H activation process. Herein, we have reported zinc ferrite nanoparticles as magnetically separable heterogeneous catalyst for A3-coupling reaction with attractive attributes like excellent productivity, selectivity and better reusability. Moreover, the catalyst can also be effectively applied for the synthesis of various NH-triazoles with quantitative yields of the products. A plausible mechanism has been proposed for the synthesis of NH-triazoles followed by validation with computational study.
Iodine-Mediated Condensation–Cyclization of α-Azido Ketones with p-Toluenesulfonyl Hydrazide for Synthesis of 4-Aryl-NH-1,2,3-Triazoles
Ren, Ming-Tian,Li, Min,Wang, An-Jing,Gao, Jie,Zhang, Xiang-Xiang,Shu, Wen-Ming
supporting information, p. 2233 - 2236 (2020/04/16)
A molecular iodine mediated condensation–cyclization reaction for the synthesis of 4-aryl-NH-1,2,3-triazoles has been developed from readily available α-azido acetophenones and p-toluenesulfonyl hydrazide. This reaction provides a metal-free strategy for the sequential formation of C–N and N–N bonds in mild condition.
Zinc Oxide Nanoparticles Catalysed One-Pot Three-Component Reaction: A Facile Synthesis of 4-Aryl-NH-1,2,3-Triazoles
Phukan, Parmita,Agarwal, Soniya,Deori, Kalyanjyoti,Sarma, Diganta
, p. 2208 - 2219 (2020/02/25)
Abstract: A facile one-pot, three component reaction has been developed using aldehydes, nitroalkane and sodium azide with zinc oxide nanocatalyst for the synthesis of 4-aryl-NH-1,2,3-triazoles. ZnO nanoparticles with controlled size (15–25?nm) and morpho
Catalyst-Free Regioselective N2 Arylation of 1,2,3-Triazoles Using Diaryl Iodonium Salts
Roshandel, Sahar,Lunn, Maiko J.,Rasul, Golam,Muthiah Ravinson, Daniel Sylvinson,Suri, Suresh C.,Prakash, G. K. Surya
supporting information, p. 6255 - 6258 (2019/08/26)
The widespread application of 1,2,3-triazoles in pharmaceuticals has resulted in substantial interest toward developing efficient postmodification methods. Whereas there are many postmodification methods available to obtain N1-substituted 1,2,3-triazoles, developing a selective and convenient protocol to synthesize N2-aryl-1,2,3-triazoles has been challenging. We report a catalyst-free and regioselective method to access N2-aryl-1,2,3-triazoles in good to excellent yields (66-97%). This scalable postmodification protocol is effective for a wide range of substrates.
