reactivity of 2-thiohydantoins towards various electrophilic reagents applications to the synthesis of new 2-ylidene-3,5-dihydro-4h-imidazol-4-ones.反应2-thiohydantoins对各种亲电试剂的合成应用新2-ylidene-3 5-dihydro-4h-imidazol-4-ones。.pdfVIP

Molecules 2004, 9, 867-875 molecules ISSN 1420-3049 Reactivity of 2-Thiohydantoins Towards Various Electrophilic Reagents: Applications to the Synthesis of New 2-Ylidene-3,5- dihydro-4H-imidazol-4-ones. Jean-René Chérouvrier 1, François Carreaux 2 and Jean Pierre Bazureau 1,* 1 Université de Rennes 1, Institut de Chimie, Synthèse Electrosynthèses Organiques 3, UMR 6510, Bât. 10A, Campus de Beaulieu, Avenue du Général Leclerc, CS 74205, 35042 RENNES Cedex, France. 2 Université de Rennes1, Institut de Chimie, Organométalliques et Catalyse : Chimie et Electrochimie Moléculaire, UMR 6509, Campus de Beaulieu, Avenue du Général Leclerc, Bât. 10A, CS 74205, 35042 RENNES Cedex, France. Tel.: (+33) (0)2 23 23 66 03, Fax : (+33) (0)2 23 23 63 74. * Author to whom correspondence should be addressed; E-mail: jean-pierre.bazureau@univ-rennes1.fr Received: 22 July 2004 / Accepted: 3 September 2004 / Published: 30 September 2004 Abstract: A new route to 5-(imidazolidin-2-ylidene)-2-methylsulfanyl-3,5-dihydro- imidazol-4-ones 4a-c using ketene dithioacetal intermediates 3a-c is described. The reactivity of thiohydantoin derivatives 2a-c towards N,N-dimethylformamide diethylacetal (DMF-DEA) was also explored using solvent-free technique under microwave irradiation (µω). The 1H- and 13C-NMR spectra of some representative products are discussed. Keywords: Thiohydantoins; ketene dithioacetal; dimethylformamide diethylacetal; microwave irradiation. Introduction There has been much interest in the synthesis and pr