Reaction of allenyl esters with sodium azide: an efficient synthesis of e-vinyl azides and polysubstituted pyrroles.
The nucleophilic addition of sodium azide to 1,2-allenyl esters can generate vinyl azides in excellent yields with excellent regio- and stereoselectivities. Moreover, pyrroles are synthesized using 1-allyllic 1,2-allenyl esters as substrates in t-BuOH at 65 degrees C. The sequential reaction for pyrroles is developed on the basis of a novel domino process involving nucleophilic addition, cycloaddition, denitrogenation, and aromatization.
Huang
Xian
X
Department of Chemistry, Zhejiang University (Xixi Campus), Hangzhou 310028, P. R. China. huangx@mail.hz.zj.cn
Shen
Ruwei
R
Zhang
Tiexin
T