ChemInform Abstract: Parallel Solution‐Phase Synthesis of 2‐Alkylthio‐5‐arylidene‐3,5‐dihydro‐4H‐imidazol‐4‐one by One‐Pot Three‐Component Domino Reaction

Abstract

Three-Component Domino Reaction -[17 examples for biological studies]. -(RENAULT, S.; BERTRAND, S.; CARREUX, F.; BAZUREAU*, J. P.; J. Comb. Chem. 9 (2007) 6, 935-942; Lab. Sci. Chim. Rennes, Univ. Rennes, F-35042 Rennes, Fr.; Eng.) -S. Adam

5-Arylidenethioxothiazolidinones as Inhibitors of Tyrosyl–DNA Phosphodiesterase I

“…Yield 63%; mp >300 °C; 3-Phenyl-2-thioxo-imidazolidin-4-one (27). 54 A suspension of methylglycinate hydrochloride (2.5 g, 20 mmol), phenylisothiocyanate (2.7 g, 20 mmol), and triethylamine (2.02 g, 2.8 mL, 20 mmol) in dry ethylacetate was refluxed (80 °C) for 2 days. Solvent was evaporated under reduced pressure.…”

Unprecedented One-Pot Chemocontrolled Entry to Thioxoimidazolidinones and Aminoimidazolones: Synthesis of Kinase Inhibitor Leucettamine B

“…Aminoimidazolones constitute an attractive template to exploit the chemical diversity of a broad drug-like library. A structure–activity relationship study on a diversified small molecule library of aminoheterocycle (III) provided a novel series of γ-secretase modulators. , …”

“…A structure−activity relationship study on a diversified small molecule library of aminoheterocycle (III) provided a novel series of γ-secretase modulators. 11,12 Normally, 4-benzylidene-substituted aminoimidazolones are synthesized by the condensation of 2-thioxoimidazolidinone (or 2-alkylthio-imidazolones) with aldehydes followed by reaction with alkylamines. 13 Ding et al assembled an aminoimidazolone ring system by the reaction of aliphatic primary amines with carbodiimides, which were generated from aza-Wittig reactions of vinylimino-phosphorane with isocyanates.…”