Microwave assisted synthesis of novel functionalized hydantoin derivatives and their conversion to 5-(Z) arylidene-4H-imidazoles

• Published in: Molecules (Basel, Switzerland) Vol. 16; no. 7; pp. 5527 - 5537
• Main Authors: Kamila, Sukanta, Ankati, Haribabu, Biehl, Edward R
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 29-06-2011; MDPI
• Subjects: arylidene-4H-imidazoles; Ethanol; hydantoin; Hydantoins - chemical synthesis; Hydantoins - chemistry; Imidazoles - chemical synthesis; Imidazoles - chemistry; Magnetic Resonance Spectroscopy; Microwaves; Molecular Structure; MW assisted synthesis; Solvents; Thiohydantoins - chemical synthesis; Thiohydantoins - chemistry
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules16075527

2-(Alkyl-1-yl)-1H-imidazol-5(4H)-ones 5a-n were synthesized via nucleophilic substitution of the methylsulfanyl group of the corresponding 2-(methylthio)-1H-imidazol-5(4H)-ones 3a-c with suitably substituted secondary amines. The starting 2-thioxo- imidazolidin-4-ones 2a,2b were prepared by condensation of thiohydantoin and benzo[b]-thiophene-3-carbaldehyde or benzofuran-3-carbaldehyde under microwave irracdiation (MW) conditions. 2-Methylthio derivatives 3a-c were prepared by treatment of 2a-b with methyl iodide in the presence of aqueous sodium hydroxide.