Microwave Assisted Synthesis of Novel Functionalized Hydantoin Derivatives and Their Conversion to 5-(Z) Arylidene-4H-imidazoles

Abstract

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.

Unusual Friedlander Reactions: A Route to Novel Quinoxaline-Based Heterocycles

“…1 In contrast, quinoxaline-based quinolines and quinoxaline-1,4-dioxides are either rare or unknown in the chemical literature. 2 Recent reviews of the biological activities of indoles, quinolines and quinoxalines point out their medicinal chemistry importance.…”