2034-28-8Relevant academic research and scientific papers
A general metal-free route towards the synthesis of 1,2,3-triazoles from readily available primary amines and ketones
Thomas, Joice,Jana, Sampad,John, Jubi,Liekens, Sandra,Dehaen, Wim
supporting information, p. 2885 - 2888 (2016/02/19)
An unprecedented approach that enables the direct and selective preparation of 1,5-disubstituted 1,2,3-triazoles from abundantly available building blocks such as primary amines, enolizable ketones and 4-nitrophenyl azide as a renewable source of dinitrogen via an organocascade process has been developed. Furthermore, this efficient methodology also enables the synthesis of fully functionalized and fused N-substituted heterocycles.
Base-mediated reaction of vinyl bromides with aryl azides: One-pot synthesis of 1,5-disubstituted 1,2,3-triazoles
Wu, Luyong,Chen, Yuxue,Luo, Jianheng,Sun, Qi,Peng, Mingsheng,Lin, Qiang
, p. 3847 - 3850 (2014/07/08)
A one-pot base-mediated reaction of azides and β- or α-vinyl bromides has been reported. The effects of bases and solvents have been investigated in the process. A variety of 1,5-disubstituted triazoles were prepared in low to good yields. Further studies reveal that the corresponding alkynes were produced as intermediates via elimination reaction. Under the same reaction conditions, the reactions of alkyl alkynes with phenyl azide would give 1,5-disubstituted 1,2,3-triazoles.
A general route to 1,5-disubstituted 1,2,3-triazoles with alkyl/alkyl, alkyl/aryl, aryl/aryl combinations: A metal-free, regioselective, one-pot three component approach
Dey, Santu,Pathak, Tanmaya
, p. 9275 - 9278 (2014/03/21)
An experimentally simple one-pot reaction, affording 1,5-disubstituted 1H-1,2,3-triazoles in good to excellent yields by combining vinyl sulfones, sodium azide and alkyl bromides, -tosylates, -mesylates or aryl amines, -iodides is reported. The organic az
A metal-free multicomponent cascade reaction for the regiospecific synthesis of 1,5-disubstituted 1,2,3-triazoles
Cheng, Guolin,Zeng, Xiaobao,Shen, Jinhai,Wang, Xuesong,Cui, Xiuling
, p. 13265 - 13268 (2014/01/06)
About specifics: A method for the regiospecific synthesis of the title compounds through an unprecedented Michael addition/deacylative diazo transfer/cyclization sequence has been established. The simple and practical method can be used for the modification of primary amines including chiral α-amines. The process involves the formation three covalent bonds and the cleavage of two covalent bonds (see scheme, Ts=4-toluenesulfonyl).
Sodium hydride-mediated synthesis of 1,5-diaryl-1,2,3-triazoles from anti-3-aryl-2,3-dibromopropanoic acids and organic azides
Cheng, Xue-Zhi,Liu, Wei,Huang, Zhen-Dong,Kuang, Chun-Xiang
, p. 764 - 766 (2013/07/26)
A series of 1,5-disubstituted 1,2,3-triazoles are synthesized by a one-pot process from anti-3-aryl-2,3-dibromopropanoic acids and organic azides mediated by sodium hydride in dimethyl sulfoxide. The reaction is mild and simple, does not require a transition-metal catalyst, and gives products in good to excellent yields.
Ln[N(SiMe3)2]3-catalyzed cycloaddition of terminal alkynes to azides leading to 1,5-disubstituted 1,2,3-triazoles: New mechanistic features
Hong, Longcheng,Lin, Weijia,Zhang, Fangjun,Liu, Ruiting,Zhou, Xigeng
, p. 5589 - 5591 (2013/07/25)
The first example of rare earth metal-catalyzed cycloaddition of terminal alkynes to azides resulting in the formation of 1,5-disubstituted 1,2,3-triazoles is described. Preliminary studies revealed that the present cycloaddition shows unprecedented mecha
Discovery of a robust and efficient homogeneous silver(I) catalyst for the cycloaddition of azides onto terminal alkynes
McNulty, James,Keskar, Kunal
, p. 5462 - 5470 (2012/10/30)
A highly efficient, chemically stable, and well-defined homogeneous silver(I) catalyst is reported for the cycloaddition of azides onto terminal alkynes (Ag-AAC reaction). The Ag-AAC reaction occurs at room temperature or with heating to deliver exclusive
Potassium tert-butoxide promoted cycloaddition reaction for the synthesis of 1,5-disubstituted 1,2,3-triazoles from aromatic azides and trimethylsilyl-protected alkynes
Wu, Luyong,Chen, Yuxue,Tang, Mi,Song, Xinming,Chen, Guangying,Song, Xiaoping,Lin, Qiang
supporting information; experimental part, p. 1529 - 1533 (2012/07/30)
The cycloaddition reaction of aromatic azides and trimethylsilyl alkynes upon treatment with desilylating reagents was investigated. In the process, the use of t-BuOK in wet DMF generated 1,5-disubstituted 1,2,3-triazoles regioselectively in moderate to g
A metal-free, aqueous and general route to 1,5-disubstituted-1,2,3- triazoles: "Reversed regioisomeric" 1,3-dipolar cycloaddition of azides and vinyl sulfones
Dey, Santu,Datta, Dhrubajyoti,Pathak, Tanmaya
, p. 2521 - 2524 (2011/12/01)
A metal-free, vinyl sulfone-based synthesis of 1,5-disubstituted-1,2,3- triazoles is reported for the first time. These triazoles are easily formed in a regioselective fashion by heating under reflux a mixture of a substituted vinyl sulfone and an organic
