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

Abstract

A practical protocol for the preparation of a parallel solution-phase library of 5-arylidene imidazolone is reported. Target compounds were obtained in good yield, stereoselectively, and purity by one-pot domino reaction from various thiohydantoines, arylaldimines, and halogenoalkanes. Purification of the final products by recrystallization with a mixture of pentane/ethanol allowed simple isolation of the 17 components of the array.

5-Arylidenethioxothiazolidinones as Inhibitors of Tyrosyl–DNA Phosphodiesterase I

“…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.…”

A Practical Approach to New (5Z) 2-Alkylthio-5-arylmethylene-1-methyl-1,5-dihydro-4H-imidazol-4-one Derivatives

“…In Method B, an equimolecular mixture of the starting hydantoin 1 and arylaldimine 3 was heated at 80 °C under microwave irradiation for the same reaction time. The arylaldimines 3 were prepared in good yields according to a solvent-free microwave protocol developed in our laboratory [31]. The reactions of both methods were conveniently monitored by 1 H- NMR or by TLC on precoated plates of silica gel with an appropriate eluant.…”

The preparation of (4H)-imidazol-4-ones and their application in the total synthesis of natural products

“…This was first reported by Daboun and Ibrahim in 1981. 60 Since then, there have been numerous reports of this transformation being used to synthesize various imidazol-4-ones for medicinal applications 61,62 and the total synthesis of natural products. [63][64][65][66][67] Scheme 19 describes the basic transformation from thiohydantoin to 2-aminoimidazol-4-one.…”