16717-74-1Relevant academic research and scientific papers
Polysubstituted 2-Aminopyrrole Synthesis via Gold-Catalyzed Intermolecular Nitrene Transfer from Vinyl Azide to Ynamide: Reaction Scope and Mechanistic Insights
Wu, Yufeng,Zhu, Lei,Yu, Yinghua,Luo, Xuesong,Huang, Xueliang
, p. 11407 - 11416 (2015/12/01)
A gold-catalyzed intermolecular reaction of vinyl azides and ynamides is described. This process presents an efficient and mild approach to multisubstituted 2-aminopyrroles in good-to-excellent yields. Control experiments were carried out to distinguish the reactivity between vinyl azides and the corresponding 2H-azirines. A plausible reaction mechanism was also proposed according to previous reports and our preliminary mechanistic studies.
Multistep flow synthesis of vinyl azides and their use in the copper-catalyzed huisgen-type cycloaddition under inductive-heating conditions
Kupracz, Lukas,Hartwig, Jan,Wegner, Jens,Ceylan, Sascha,Kirschning, Andreas
supporting information; experimental part, p. 1441 - 1448 (2011/12/14)
The multistep flow synthesis of vinyl azides and their application in the synthesis of vinyltriazoles is reported. The synthesis relies on a stable polymer-bound equivalent of iodine azide that serves to carry out 1,2-functionalization of alkenes in a telescope flow protocol. The intermediate 2-iodo azides are subjected to a DBU-mediated polymer-supported elimination step yielding vinyl azides in good yield. The third step involves the formation of vinyl triazoles by a copper-catalyzed Huisgen-"click" cycloaddition. The required heat is generated by electromagnetic induction based on copper. Copper serves both as heatable as well as catalytically active packed-bed material inside the flow reactor.
