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...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2004-09, Vol.9 (10), p.867-875
Main Authors: Chérouvrier, Jean-René, Carreaux, François, Bazureau, Jean Pierre
Format: Article
Language:English
Subjects:
dimethylformamide diethylacetal
Electrons
Imidazoles - chemical synthesis
Imidazoles - chemistry
Indicators and Reagents - chemistry
ketene dithioacetal
Ketones - chemical synthesis
Ketones - chemistry
Kinases
microwave irradiation
Models, Molecular
Potash
Potassium
Reagents
Thiohydantoins
Thiohydantoins - chemistry
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Summary: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/91000867