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 intermediates. Comparative experiments in solution were also performed. The successful preparation of an antibacterial agent precursor was also investigated.
Université de Montpellier, Institut des Biomolécules Max Mousseron UMR 5247 CNRS, ENSCM , Place E. Bataillon, Campus Triolet, cc 1703, 34095 Montpellier, France.
Laure
L
Konnert
Université de Montpellier, Institut des Biomolécules Max Mousseron UMR 5247 CNRS, ENSCM , Place E. Bataillon, Campus Triolet, cc 1703, 34095 Montpellier, France.
Lori
L
Gonnet
Ruđer Bošković Institute , Bijenička cesta 54, Zagreb, Croatia.
Ivan
I
Halasz
Institut Charles Gerhardt Montpellier (ICGM), UMR 5253 CNRS-UM-ENSCM, Ecole Nationale Supérieure de Chimie , 8 Rue de l'Ecole Normale, 34296 Montpellier Cedex 5, France.
Jean-Simon
JS
Suppo
Institut Charles Gerhardt Montpellier (ICGM), UMR 5253 CNRS-UM-ENSCM, Ecole Nationale Supérieure de Chimie , 8 Rue de l'Ecole Normale, 34296 Montpellier Cedex 5, France.
Renata Marcia
RM
de Figueiredo
Institut Charles Gerhardt Montpellier (ICGM), UMR 5253 CNRS-UM-ENSCM, Ecole Nationale Supérieure de Chimie , 8 Rue de l'Ecole Normale, 34296 Montpellier Cedex 5, France.
Jean-Marc
JM
Campagne
Université de Montpellier, Institut des Biomolécules Max Mousseron UMR 5247 CNRS, ENSCM , Place E. Bataillon, Campus Triolet, cc 1703, 34095 Montpellier, France.
Fredéric
F
Lamaty
Université de Montpellier, Institut des Biomolécules Max Mousseron UMR 5247 CNRS, ENSCM , Place E. Bataillon, Campus Triolet, cc 1703, 34095 Montpellier, France.
Jean
J
Martinez
Université de Montpellier, Institut des Biomolécules Max Mousseron UMR 5247 CNRS, ENSCM , Place E. Bataillon, Campus Triolet, cc 1703, 34095 Montpellier, France.
Evelina
E
Colacino