53887-79-9Relevant academic research and scientific papers
N, N -diethylurea-catalyzed amidation between electron-deficient aryl azides and phenylacetaldehydes
Xie, Sheng,Ramstr??m, Olof,Yan, Mingdi
, p. 636 - 639 (2015)
Urea structures, of which N,N-diethylurea (DEU) proved to be the most efficient, were discovered to catalyze amidation reactions between electron-deficient aryl azides and phenylacetaldehydes. Experimental data support 1,3-dipolar cycloaddition between DEU-activated enols and electrophilic phenyl azides, especially perfluoroaryl azides, followed by rearrangement of the triazoline intermediate. The activation of the aldehyde under near-neutral conditions was of special importance in inhibiting dehydration/aromatization of the triazoline intermediate, thus promoting the rearrangement to form aryl amides.
