Synthesis of novel NH-1,2,3-triazolo-nucleosides by the Banert cascade reaction
Mariola Koszytkowska-Stawińska , Wojciech Sas
AbstractNucleoside analogs with the 4,5-dimethyl-NH-1,2,3-triazolo-linker between thymine and a carbohydrate, or a hydroxyalkoxyl, or phosphonomethoxyl residue, were obtained by the Bannert cascade reaction from 1-(4-azidobut-2-yn-1-yl)thymine and the carbohydrate or acyclic alcohol. The reaction conditions were developed on the basis of a thermal analysis of the starting azide and by the optimization of the reaction components ratio. The best results were obtained when the reaction cascade employed the azide/nucleophile molar ratio of 1/14, at 55 °C, with no solvent addition. The reaction showed good discrimination between the pentofuranose hydroxyls, yielding triazoles linked at the carbohydrate 5′-oxygen atom.
|Journal series||Tetrahedron, ISSN 0040-4020|
|Publication size in sheets||0.5|
|Keywords in English||nucleoside analogs, fleximers, NH-1,2,3-Triazoles, propargyl azides, Banert cascade reaction|
|ASJC Classification||; ;|
|Score|| = 30.0, 01-01-2020, ArticleFromJournal|
= 30.0, 01-01-2020, ArticleFromJournal
|Publication indicators||= 11; = 9; : 2014 = 0.905; : 2013 = 2.817 (2) - 2013=2.772 (5)|
|Citation count*||2 (2015-05-22)|
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.