18411-23-9Relevant academic research and scientific papers
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
, p. 6259 - 6262 (2017)
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.
AgNO3as Nitrogen Source for Cu-Catalyzed Cyclization of Oximes with Isocyanates: A Facile Route to N-2-Aryl-1,2,3-triazoles
Liang, Jingwen,Rao, Yingqi,Zhu, Weidong,Wen, Tingting,Huang, Junjie,Chen, Zhichao,Chen, Lu,Li, Yibiao,Chen, Xiuwen,Zhu, Zhongzhi
supporting information, p. 7028 - 7032 (2021/09/14)
A versatile copper-catalyzed [3 + 1 + 1] annulation of oximes and isocyanates with AgNO3 is described. In this conversion, AgNO3 and isocyanates instead of conventional azide or diazonium reagents were used as the nitrogen source. This three-component transformation was achieved by cleaving N-O/C-H/C-N bonds and building CN/N-N bonds, which provides a strategy to prepare N-2-aryl-1,2,3-triazoles with a good substrate and functional compatibility.
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
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.
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.
