6111-96-2Relevant academic research and scientific papers
A Scalable Metal-, Azide-, and Halogen-Free Method for the Preparation of Triazoles
Clark, Peter R.,Hayes, Jerome F.,Tomkinson, Nicholas C. O.,Williams, Glynn D.
supporting information, p. 6740 - 6744 (2020/03/23)
A scalable metal-, azide-, and halogen-free method for the synthesis of substituted 1,2,3-triazoles has been developed. The reaction proceeds through a 3-component coupling of α-ketoacetals, tosyl hydrazide, and a primary amine. The reaction shows outstanding functional-group tolerance with respect to both the α-ketoacetal and amine coupling partners, providing access to 4-, 1,4-, 1,5-, and 1,4,5-substituted triazoles in excellent yield. This robust method results in densely functionalised 1,2,3-triazoles that remain challenging to prepare by azide–alkyne cycloaddition (AAC, CuAAC, RuAAC) methods and can be scaled in either batch or flow reactors. Methods for the chemoselective reaction of either aliphatic amines or anilines are also described, revealing some of the potential of this novel and highly versatile transformation.
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.
Regioselective N/C-heterocyclization of allenylindium bromide across aryl azides: One-pot synthesis of 5-methyl-1,2,3-triazoles
Banday, Abid H.,Hruby, Victor J.
, p. 1859 - 1862 (2014/08/18)
An unprecedented, one-pot regioselective synthesis of 1,5-disubstituted 1,2,3-triazoles through N/C-heterocyclization of allenylindium bromide across aryl azides is described. The synthesis is carried out under mild conditions in aqueous medium and procee
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
supporting information, 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).
CYCLOADDITION DES METHYLAZIDE ET PHENYLAZIDE AU β-NITROSTYRENE ET AU NITROPROPENE HOMOLOGUE
Cailleux, P.,Piet, J. C.,Benhaoua, H.,Carrie, R.
, p. 45 - 52 (2007/10/03)
Phenylazide and methylazide reacts with title olefines and gives two isomeric triazoles without nitro group, and 4-nitro-1,2,3 triazole.The isomerisation of starting alkenes explains the formation of isomeric triazoles.Oxydation of amino-nitro-diazocompounds in equilibrium with 1,2,3 triazolines leads to 4-nitro-1,2,3 triazoles.
Aryl Azide-Allene Cycloaddition. The Contrasting Behavior of Two Simple Allenes, 1,2-Cyclononadiene and 1,2-Propadiene
Wedegaertner, Donald K.,Kattak, Rangin K.,Harrison, Isom,Cristie, Sharon K.
, p. 4463 - 4467 (2007/10/02)
1,2-Cyclononadiene (1) reacts with phenyl azide (2a) and 4-bromophenyl azide (2b) to give conjugated triazoline adducts 3a and 3b, respectively. (R)-(+)-1 and 2a react to give (S)-(+)-3a, which is consistent with a concerted cycloaddition mechanism.The reaction of 1,2-propadiene (6) and 2a gives triazoles 8 and 10 plus compound 18 in nearly equal amounts.The formation of these products is rationalized by a scheme involving initial formation of triazolines 7 and 9.Triazoline 3a is slowly isomerized by sodium ethoxide or N,N-dimethylaniline to triazole 20.
