18922-69-5Relevant articles and documents
General solution to the synthesis of N-2-substituted 1,2,3-triazoles
Wang, Xiao-Jun,Zhang, Li,Krishnamurthy, Dhileepkumar,Senanayake, Chris H.,Wipf, Peter
scheme or table, p. 4632 - 4635 (2010/12/18)
The regioselective N-alkylation of 1,2,3-triazoles 1 - 6 was studied. Good to excellent N-2 selectivity and high chemical yields for N-2-substituted 4,5-dibromotriazoles 7 were obtained with 4,5-dibromo- and 4-bromo-5- trimethylsilyl-1,2,3-triazoles. These building blocks can be readily converted to 2-mono-, 2,4-di-, and 2,4,5-polysubstituted triazoles 10 - 15, providing a general, protective, group-free method for the synthesis of N-2-substituted triazoles. Observed regioselectivities can be rationalized by a combination of Frontier Molecular Orbital, steric, and electrostatic directing effects on the heterocyclic scaffolds.
UNSATURATED CARBONYL-CONTAINING COMPOUNDS. XXVIII. CYCLOADDITION OF ORGANIC AZIDES TO α-ACETYLENIC KETONES AND ACIDS
Vereshchagin, L. I.,Tikhonova, L. G.,Maksikova, A. V.,Serebryakova, E. S.,Proidakov, A. G.,Filippova, T. M.
, p. 641 - 648 (2007/10/02)
The reaction of α-acetylenic ketones and acids with organic azides leads to the formation of 1-alkyl(aryl)-4-acyl(carboxy)-1,2,3-triazoles or to a mixture of the 1,4- and 1,5-disubstituted isomers.The effect of the structure of the initial compound and of the solvent on the direction of cycloaddition was investigated.
