Mechanochemical Preparation of 3,5-Disubstituted Hydantoins from Dipeptides and Unsymmetrical Ureas of Amino Acid Derivatives

5-Substituted-3-(alkoxycarbonyl)­alkyl-hydantoin derivatives were prepared by mechanochemistry from amino esters or dipeptides, via a 1,1′-carbonyldiimidazole-mediated one-pot/two-step cyclization reaction involving amino acid unsymmetrical urea A and carboxy-imidazolyl-dipeptide ester B intermediat...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2016-10, Vol.81 (20), p.9802-9809
Main Authors: Konnert, Laure, Gonnet, Lori, Halasz, Ivan, Suppo, Jean-Simon, de Figueiredo, Renata Marcia, Campagne, Jean-Marc, Lamaty, Fredéric, Martinez, Jean, Colacino, Evelina
Format: Article
Language:English
Subjects:
Chemical Sciences
Organic chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:5-Substituted-3-(alkoxycarbonyl)­alkyl-hydantoin derivatives were prepared by mechanochemistry from amino esters or dipeptides, via a 1,1′-carbonyldiimidazole-mediated one-pot/two-step cyclization reaction involving amino acid unsymmetrical urea A and carboxy-imidazolyl-dipeptide ester B intermediates. Comparative experiments in solution were also performed. The successful preparation of an antibacterial agent precursor was also investigated.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b01832