220958-33-8Relevant academic research and scientific papers
Copper-Catalyzed Hydroamination of N-Allenylazoles: Access to Amino-Substituted N-Vinylazoles
Perego, Luca Alessandro,Blieck, Rémi,Michel, Julie,Ciofini, Ilaria,Grimaud, Laurence,Taillefer, Marc,Monnier, Florian
supporting information, p. 4388 - 4392 (2017/10/23)
Building on mechanistic studies, the innate capability of azoles to act as a directing group has been exploited to design an efficient and simple procedure for the hydroamination of N-allenylazoles with secondary amines. The reaction proceeds under mild conditions by copper(I) catalysis yielding the corresponding original linear E allylic amines with total regio- and stereoselectivity. Density Functional Theory (DFT) calculations offer a mechanistic explanation of the significantly higher reactivity of N-allenyl-(1,2)-azoles compared to their 1,3-analogues as a result of the reaction-enhancing coordination of the pyridine-like nitrogen to the copper center. (Figure presented.).
N-Allenylation of Pyrrole, Diazoles, and Triazoles with 2-Propynyl Bromide in the System KOH-DMSO
Tarasova,Shmidt,Klyba,Sinegovskaya,Mikhaleva,Krivdin,Trofimov
, p. 688 - 692 (2007/10/03)
Pyrrole, pyrazole, imidazole, 2-methylimidazole, and 1,2,4-triazole react with 2-propynyl bromide in the system KOH-DMSO to give in one step the corresponding N-allenyl derivatives in good yields and with an isomeric purity of 98-100%.
