27653-10-7Relevant academic research and scientific papers
General Synthesis of Tri-Carbo-Substituted N2-Aryl-1,2,3-triazoles via Cu-Catalyzed Annulation of Azirines with Aryldiazonium Salts
Cheung, Chi Wai,Feng, Fang-Fang,Li, Jun-Kuan,Liu, Xuan-Yu,Ma, Jun-An,Zhang, Fa-Guang
, p. 10872 - 10883 (2020/09/23)
The general synthesis of fully substituted N2-aryl-1,2,3-triazoles is hitherto challenging compared with that of the N1-aryl counterparts. Herein, we describe a Cu-catalyzed annulation reaction of azirines and aryldiazonium salts. This regiospecific metho
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
, 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.
Copper(i)-mediated carboamination of vinyl azides by aryldiazonium salts: Synthesis of: N 2-substituted 1,2,3-triazoles
Liu, Zhenhua,Ji, Huimin,Gao, Wen,Zhu, Guangyu,Tong, Lili,Lei, Fengcai,Tang, Bo
supporting information, p. 6259 - 6262 (2017/07/10)
A copper(i)-mediated carboamination cascade reaction between vinyl azides and aryldiazonium salts is described. Functionally diverse N2-substituted 1,2,3-triazoles were obtained in moderate to good yields through novel difunctionalization of vinyl azides by aryldiazonium salt sources. This method has a wide scope, good functional-group tolerance and insensitivity to an ambient atmosphere.
Regiospecific Synthesis of N 2-Aryl 1,2,3-Triazoles from 2,5-Disubstituted Tetrazoles via Photochemically Generated Nitrile Imine Intermediates
Stewart, Sam,Harris, Robert,Jamieson, Craig
, p. 2480 - 2484 (2015/07/27)
The synthesis of N2-aryl 1,2,3-triazoles from 2,5-disubstituted tetrazoles was achieved under photochemical conditions. This simple and mild one-step reaction provides regiospecific access to 2,4,5-substituted 1,2,3-triazoles via a nitrile imine intermediate. Syntheses of alkyl and heterocylic derivatives were also investigated.
A one-pot synthesis of bisarylhydrazones by Cu(I)-catalyzed aerobic oxidation
Hu, Jiu-Rong,Zhang, Wan-Jia,Zheng, Da-Gui
, p. 9865 - 9869 (2013/10/22)
An efficient Cu(I)-catalyzed one-pot synthesis of N-substituted (or NH) bisarylhydrazones is reported. A further cyclization reaction could occur towards the synthesis of benzimidazoles or triazoles with elevated temperature. A plausible alkylation-oxidation-alkylation mechanism is proposed based on experimental results and literature.
Copper(II)-catalyzed aerobic oxidative synthesis of substituted 1,2,3- and 1,2,4-triazoles from bisarylhydrazones via C-H functionalization/C-C/N-N/C-N bonds formation
Guru, Murali Mohan,Punniyamurthy, Tharmalingam
experimental part, p. 5063 - 5073 (2012/07/16)
An unprecedented copper(II)-catalyzed aerobic oxidative synthesis of 2,4,5-triaryl-1,2,3-triazoles and 1,3,5-triaryl-1,2,4-triazoles from bisarylhydrazones as the common starting precursor has been achieved via cascade C-H functionalization/C-C/N-N/C-N bonds formation under mild reaction conditions. One of the enthralling outcomes of this strategy is the copper(II)-catalyzed room temperature C-H functionalization/C-N bond formation in presence of air, which has been accomplished during the synthesis of substituted 1,2,4-triazoles. This new class of compounds could give prospective luminescence as an iconic component in the area of pharmaceutical and biological sciences. The intermediates for both the processes have been isolated to elucidate the mechanistic scenario.
Simple and efficient one-pot synthesis of 2,4-diaryl-1,2,3-triazoles
Tang, Wen-Jie,Hu, Yong-Zhou
, p. 2461 - 2468 (2007/10/03)
A general and efficient method for the preparation of 2,4-diaryl-1,2,3- triazoles from α-hydroxyacetophenones and phenylhydrazines is reported. The essential characteristics of this method include mild reaction conditions, a straight-forward workup proced
Ring expansions of N-methyl-1,2,5-oxadiazolium and 1,2,3-triazolium perchlorate salts with bases to six-membered azines: Direct detection of an addition intermediate in an addition-elimination mechanism and a degradation of 1,2,5-oxadiazolium salts to aα-cyano nitrones
Butler, Richard N.,McKenna, Elaine C.,McMahon, John M.,Daly, Karen M.,Cunningham, Desmond,McArdle, Patrick
, p. 2919 - 2923 (2007/10/03)
Reactions of 2-methyl-1,2,5-oxadiazolium perchlorate salts and 1-methyl-2-aryl-1,2,3-triazolium perchlorate salts with the bases KCN, NaOEt, KOBuf, LiNPrl2 give ring expansions to substituted 1,2,5-oxadiazines and 1,2,4-triazines. With cyanide as base the reactions follow an addition-elimination pathway and in two cases the addition intermediate has been isolated or directly detected by low-temperature NMR spectroscopy. The oxadiazolium system with cyanide also gives a useful new route to α-cyano nitrones via a ring degradation which competes with ring expansion. The reactions with KOBut and LiNPri2 do not involve an addition of the base to the azolium salt. Reactions have been monitored by 13C NMR spectroscopy by using 13CN-. An X-ray crystal structure is reported for (E)-N-(α-cyanobenzylidene)methylamine N-oxide.
