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

Authors :
Ivan Halasz
Jean-Simon Suppo
Renata Marcia de Figueiredo
Jean-Marc Campagne
Evelina Colacino
Laure Konnert
Frédéric Lamaty
Lori Gonnet
Jean Martinez
Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM)
Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)
Rudjer Boskovic Institute [Zagreb]
Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM)
Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC)
Source :
Journal of Organic Chemistry, Journal of Organic Chemistry, American Chemical Society, 2016, 81 (20), pp.9802-9809. ⟨10.1021/acs.joc.6b01832⟩
Publication Year :
2016
Publisher :
American Chemical Society (ACS), 2016.

Abstract

International audience; 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.

Details

ISSN :
15206904 and 00223263
Volume :
81
Database :
OpenAIRE
Journal :
The Journal of Organic Chemistry
Accession number :
edsair.doi.dedup.....eb00a73718294de0a1de8c936f7bf079
Full Text :
https://doi.org/10.1021/acs.joc.6b01832