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

Laure Konnert (1) , Lori Gonnet (1) , Ivan Halasz (2) , Jean-Simon Suppo (3) , Renata Marcia de Figueiredo (3) , Jean-Marc Campagne (3) , Frederic Lamaty (1) , Jean Martinez (1) , Evelina Colacino (1)

1 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]
2 Rudjer Boskovic Institute [Zagreb]
3 ICGM - Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier

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.

Mots clés: Hydantoin; ball-mill; amino acid; CDI; carbonyl diimidazole; Dipeptide; Mechanochemistry; Mechanosynthesis

Domaines: Chimie organique

Laure Konnert, Lori Gonnet, Ivan Halasz, Jean-Simon Suppo, Renata Marcia de Figueiredo, et al.. Mechanochemical Preparation of 3,5-Disubstituted Hydantoins from Dipeptides and Unsymmetrical Ureas of Amino Acid Derivatives. Journal of Organic Chemistry, 2016, 81 (20), pp.9802-9809. ⟨10.1021/acs.joc.6b01832⟩. ⟨hal-01396871⟩