117573-59-8Relevant articles and documents
A reliable one-pot synthesis of aryl azides from aryl amines using organotin azides as effective and recoverable reagents
Godoy Prieto, Leonela,Lo Fiego, Marcos J.,Chopa, Alicia B.,Lockhart, María T.
supporting information, p. 26 - 32 (2016/12/18)
A mild and mass-efficient procedure based on the one-pot diazotization-azidodediazoniation of aromatic amines is described. A wide range of aryl azides are obtained in moderate to high yields by using tributyltin azide as an effective and reusable azide source in the presence of p-toluenesulfonic acid at room temperature. The method was also successfully applied employing an insoluble polymer-supported organotin azide.
ZINClick: A database of 16 million novel, patentable, and readily synthesizable 1,4-disubstituted triazoles
Massarotti, Alberto,Brunco, Angelo,Sorba, Giovanni,Tron, Gian Cesare
, p. 396 - 406 (2014/03/21)
Since Professors Sharpless, Finn, and Kolb first introduced the concept of click reactions in 2001 as powerful tools in drug discovery, 1,4-disubstituted-1,2,3-triazoles have become important in medicinal chemistry due to the simultaneous discovery by Sharpless, Fokin, and Meldal of a perfect click 1,3-dipolar cycloaddition reaction between azides and alkynes catalyzed by copper salts. Because of their chemical features, these triazoles are proposed to be aggressive pharmacophores that participate in drug-receptor interactions while maintaining an excellent chemical and metabolic profile. Surprisingly, no virtual libraries of 1,4-disubstituted-1,2,3-triazoles have been generated for the systematic investigation of the click-chemical space. In this manuscript, a database of triazoles called ZINClick is generated from literature-reported alkynes and azides that can be synthesized within three steps from commercially available products. This combinatorial database contains over 16 million 1,4-disubstituted-1,2,3-triazoles that are easily synthesizable, new, and patentable! The structural diversity of ZINClick (http://www.symech.it/ZINClick) will be explored. ZINClick will also be compared to other available databases, and its application during the design of novel bioactive molecules containing triazole nuclei will be discussed.
Efficient conversion of aromatic amines into azides: A one-pot synthesis of triazole linkages
Barral, Karine,Moorhouse, Adam D.,Moses, John E.
, p. 1809 - 1811 (2008/02/02)
An efficient and improved procedure for the preparation of aromatic azides and their application in the Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition ("click reaction") is described. The synthesis of aromatic azides from the corresponding amies i
Parallel fluorous biphasic synthesis of 3H-quinazolin-4-ones by an Aza-Wittig reaction employing perfluoroalkyl-tagged triphenylphosphine
Barthélémy, Sophie,Schneider, Siegfried,Bannwarth, Willi
, p. 807 - 810 (2007/10/03)
A perfluoroalkyl-tagged triphenylphosphine was applied in a fluorous biphasic system for the efficient parallel synthesis of 3H-quinazolin-4-ones via an Aza-Wittig reaction. The products were isolated by solid-phase extraction on fluorous reversed-phase silica gel. A new solid-phase bound phosphine derivative was used for comparison and yielded similar results.
