Poly(ethylene glycol)s as grinding additives in the mechanochemical preparation of highly functionalized 3,5-disubstituted hydantoins

Andrea Mascitti; Massimiliano Lupacchini; Ruben Guerra; Ilya Taydakov; Lucia Tonucci; Nicola d'Alessandro; Frederic Lamaty; Jean Martinez; Evelina Colacino

doi:10.3762/bjoc.13.3

Poly(ethylene glycol)s as grinding additives in the mechanochemical preparation of highly functionalized 3,5-disubstituted hydantoins

Beilstein J Org Chem. 2017 Jan 4:13:19-25. doi: 10.3762/bjoc.13.3. eCollection 2017.

Authors

Andrea Mascitti^#^{1

2}, Massimiliano Lupacchini^#^{1

2}, Ruben Guerra², Ilya Taydakov^{3

4}, Lucia Tonucci⁵, Nicola d'Alessandro¹, Frederic Lamaty², Jean Martinez², Evelina Colacino²

Affiliations

¹ Department of Engineering and Geology (INGEO), G.d'Annunzio University of Chieti-Pescara, Via dei Vestini, 31, 66100 Chieti Scalo, Italy.
² Université de Montpellier, Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS - UM - ENSCM, Place E. Bataillon, Campus Triolet, 34095 Montpellier CEDEX 5, France.
³ P.N. Lebedev Institute of Physics of RAS, Leninskiy pr-t, 53, 119991, Moscow, Russia.
⁴ Moscow Institute of Physics and Technology, Institutskiy per., 9, 141700, Dolgoprudny, Russia.
⁵ Department of Philosophical, Educational and Economic Sciences, G. d'Annunzio University of Chieti-Pescara, Via dei Vestini, 31, 66100 Chieti Scalo, Italy.

^# Contributed equally.

Abstract

The mechanochemical preparation of highly functionalized 3,5-disubstituted hydantoins was investigated in the presence of various poly(ethylene) glycols (PEGs), as safe grinding assisting agents (liquid-assisted grinding, LAG). A comparative study under dry-grinding conditions was also performed. The results showed that the cyclization reaction was influenced by the amount of the PEG grinding agents. In general, cleaner reaction profiles were observed in the presence of PEGs, compared to dry-grinding procedures.

Keywords: 1,1’-carbonyldiimidazole (CDI); ball-milling; hydantoins; liquid-assisted grinding (LAG); mechanochemistry; poly(ethylene) glycols (PEGs).