Reactivity of 2-Thiohydantoins Towards Various Electrophilic Reagents Applications to the Synthesis of New 2-Ylidene-3,5-dihydro-4H-imidazol-4-ones. 英文参考文献.docVIP

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Reactivity of 2-Thiohydantoins Towards Various Electrophilic Reagents Applications to the Synthesis of New 2-Ylidene-3,5-dihydro-4H-imidazol-4-ones. 英文参考文献.doc

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Reactivity of 2-Thiohydantoins Towards Various Electrophilic Reagents Applications to the Synthesis of New 2-Ylidene-3,5-dihydro-4H-imidazol-4-ones. 英文参考文献

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 , Fran?ois Carreaux and Jean Pierre Bazureau * 2 1, 1 2 Université de Rennes 1, Institut de Chimie, Synthèse Electrosynthèses Organiques 3, UMR 6510, Bat. 10A, Campus de Beaulieu, Avenue du Général Leclerc, CS 74205, 35042 RENNES Cedex, France. Université de Rennes1, Institut de Chimie, Organométalliques et Catalyse : Chimie et Electrochimie Moléculaire, UMR 6509, Campus de Beaulieu, Avenue du Général Leclerc, Bat. 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 H- and C-NMR spectra of some representative products are discussed. 1 13 Keywords: Thiohydantoins; ketene dithioacetal; dimethylformamide diethylacetal; microwave irradiation. Introduction There has been much interest in the synthesis and properties of 2-thiohydantoin derivatives that are useful synthetic intermediates with a wide range of applications as therapeutics [1] as well as Molecules 2004, 9 868 fungicides and herbicides [2]. Furthermore, several 5-arylidene-3-aryl-2-thiohydantoins and their S- glucos