6111-96-2Relevant articles and documents
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.