Poly(ethylene) glycols and mechanochemistry for the preparation of bioactive 3,5-disubstituted hydantoins

Abstract

Mechanochemistry was effective for the preparation of 3,5-disubstituted hydantoins from α-amino methyl esters, using either 1,1′-carbonyldiimidazole (CDI) or alkyl isocyanates. The preparation of the antimicrobial additives, 3-allyl-5,5′-dimethyl hydantoin (ADMH) and 1-chloro-3-ethyl-5,5′-dimethyl hydantoin (CEDMH) were performed by grinding. A chlorination reaction, never described before by mechanochemistry was achieved by Ca(ClO)₂, while the preparation of the bioactive anticonvulsant marketed drug ethotoin was achieved by a novel approach based on poly(ethylene) glycol (PEGs) assisted grinding.