Fluorine containing bioactive heterocycles. PartII. Synthesis of some new fluorine containing arylglyoxals, their hydrates and 1,5‐disubstituted hydantoins

Abstract

Eight new fluorine containing arylglyoxals have been synthesized by the oxidation of the active methyl group of fluorinated acetophenones by selenium dioxide in dioxan-water medium. The corresponding hydrates were obtained by dissolving arylglyoxals in minimum amounts of benzene and adding hot water. Seventeen new fluorine containing 1,5-disubstituted hydantoins were subsequently prepared by the condensation of these arylglyoxals with arylureas in ethanol and characterized by ir, pmr and mass spectral studies. Representative compounds have been screened for their possible anticonvulsant and analgesic activities. None of the compounds show significant analgesic acitivity.

Synthesis and Activity of 1,3,5-Triphenylimidazolidine-2,4-diones and 1,3,5-Triphenyl-2-thioxoimidazolidin-4-ones: Characterization of New CB1 Cannabinoid Receptor Inverse Agonists/Antagonists

“…The 1,5-diphenylimidazolidine-2,4-dione derivatives ( 6 , 8 − 14 , X‘ = O) were synthesized from phenylglyoxal and phenylurea by slightly modifying the procedure described by Joshi et al (Scheme ). Four hours of reflux in an acetic acid−hydrochloric acid mixture yielded the 1,5-diphenylimidazolidine-2,4-dione derivatives in good yields (59−64%).…”

Synthesis and anti-HIV activity evaluation of new phenyl ethyl thiourea (PET) derivatives

“…9 The reaction between 4a-f and 5 has been promoted by catalytic amounts of the mixture acetic acid/hydrochloric acid in dioxane. By maintaining unchanged the reaction conditions and switching the solvent from dioxane to ethanol, it was possible to obtain N 1 -(1-ethoxy-2-oxo-2-phenylethyl)-N 3 -pyridin-2-ylthioureas 2a-f, realistically due to the addition of ethanol to the N-aroylmethylene thiourea intermediate.…”

Improved Synthesis of 5-Aryl-2-thioxoimidazolidin-4-ones from Arylglyoxals Hydrates

“…Also, it must be noted that 1,5-diarylhydantoins (2b) had also been prepared by arylglyoxals condensation with Narylureas in the presence of hydrochloric acid and acetic acid in boiling ethanol for 4 h. 6 It is obviously that 1-aryl-5-arylthiohydantoins formation from arylglyoxals hydrates and thiourea takes place in the presence of strong acid [3][4][5] or in boiling acetic acid solution. 2 But the course of this reaction in acetic acid media at room temperatures has not been studied.…”