56020-04-3Relevant academic research and scientific papers
One-Pot, Metal- And Azide-Free Synthesis of 1,2,3-Triazoles from α-Ketoacetals and Amines
Hawkins, Joel M.,Sutton, Scott C.,Zehnder, Luke R.
supporting information, p. 175 - 178 (2020/01/23)
An efficient one-pot two-step synthesis of 1,4-disubstituted 1,2,3-triazoles from α-ketoacetals and amines is presented. The method does not use metals, azides, or oxidants, and is compatible with a variety of functional groups, including heterocycles, esters, nitriles, and carbamates.
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.
