Reactivity of 2-thiohydantoins towards various electrophilic reagents: applications to the synthesis of new 2-ylidene-3,5-dihydro-4H-imidazol-4-ones.
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 (mu omega). The (1)H- and (13)C-NMR spectra of some representative products are discussed.
Chérouvrier
Jean-René
JR
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.
Carreaux
François
F
Bazureau
Jean Pierre
JP
D004583:Electrons; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D013867:Thiohydantoins / Q000737:chemistry*
D007093:Imidazoles; D007202:Indicators and Reagents; D007659:Ketones; D013867:Thiohydantoins