CHEMOSELECTIVE ALCOHOLYSIS OF ACYLUREAS

Authors
KISHIKAWA K EIDA H KOHMOTO S YAMAMOTO M YAMADA K
Citation
K. Kishikawa et al., CHEMOSELECTIVE ALCOHOLYSIS OF ACYLUREAS, Synthesis, (2), 1994, pp. 173-175
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
2
Year of publication
1994
Pages
173 - 175
Database
ISI
SICI code
0039-7881(1994):2<173:CAOA>2.0.ZU;2-V
Abstract
Two methods for the chemoselective alcoholysis of acylureas were devel oped to generate esters and amides, respectively. In alcoholysis using sodium methoxide in methanol, methoxide attacked the acyl carbonyl to give the corresponding methyl ester. While in alcoholysis using lithi um benzyloxide in diethyl ether, benzyloxide attacked the urea carbony l to give the amide. The chemoselectivity originates in the different chelating abilities of the metals and the polarity of the solvents.