Download PDF
Synthesis 1994; 1994(2): 173-175
DOI: 10.1055/s-1994-25432
short paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Chemoselective Alcoholysis of Acylureas

Keiki Kishikawa* , Hiroshi Eida, Shigeo Kohmoto, Makoto Yamamoto, Kazutoshi Yamada
  • *Department of Materials Science, Faculty of Engineering, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263, Japan
Further Information

Publication History

Publication Date:
17 September 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

Two methods for the chemoselective alcoholysis of acylureas were developed 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 lithium benzyloxide in diethyl ether, benzyloxide attacked the urea carbonyl to give the amide. The chemoselectivity originates in the different chelating abilities of the metals and the polarity of the solvents.

      >