Imidazolidine-2,4-dione

Chlorosulfonyl isocyanate is uniquely useful for the formation of hy-dantoins from sterically hindered acid- and base-labile amino nitriles, e.g., the synthesis of optically active spirohydantoins such as the biologically active (4S)-2,3-dihydro-6-fluorospiro(4H-1 -benzopyran-4,4 -imidazolidine)-2, 5 -dione.23... 

Table 8.5. IN VITRO AND IN VIVO AR INHIBITORY ACTIVITIES OF 2,3-DIHYDRO[4tf ]- l-BENZOPYRAN-4,4 -IMIDAZOLIDINE-2, 5 -DIONES... 

DIPHENTOIN DIPHENYLAN SODIUM DIPHENYLHYDANTOIN SODIUM 5,5-DIPHENYL-HYDANTOIN SODIUM 5,5-DIPHENYL-2,4-IMIDAZOLIDINE-DIONE, MONOSODIUM SALT DI-PHETINE DITOIN DIVULSAN DPH ENKEFAL... 

DIPHENYL-2,4-IMIDAZOLIDINE-DIONE, MONOSODIUM SALT see DNUOOO DIPHENYL KETONE see BCS250 DIPHEN"YLMERCURY see DWX)800 DIPHENYLMETHAN-4,4 -DIISOCYANAT(GERMAN ) see MJP400... 

More recently a whole series of derivatives with excellent fungicidal action has been discovered, in which the heterocyclic part is mostly pyrrolidine dione, oxazolidine dione or imidazolidine dione, while the analogous functional group is N-(3,5-dichlorophenyl) dicarboximide. 

Hydantoin — see also Imidazolidine-2,4-dione Hydantoin, 3-aryl-5-benzyl-structure, 5, 351... 

A benzodiazepine-2-4-dione derivative (153c) is formed as a minor product (12%) in a mixture containing imidazolidines (153a, b) from the iron penta-... 

K. Ienaga, K. Nakamura, A. Ishii, T. Taga, Y. Miwa, F. Yoneda, The Stepwise Mammalian Oxidation of the Hydantoin l-Methyl-imidazolidine-2,4-dione into Methylimi-dazolidinetrione via 5-Hydroxy-l-methyl-imidazolidine-2,4-dione , J. Chem. Soc. Perkin Trans. 1 1989, 1153-1156. 

Sodio-5-(5 -nitro-2 -furfurylideneamino)imidazolidin-2,4-dione, 2903 Sodium abietate, 3799 Sodium acetate, 0775... 

Chemical Name l- [5-(4-Chlorophenyl)furan-2-ylmethylene]amino -3-[4-(4-methylpiperazin-l-yl)butyl]imidazolidine-2,4-dione dihydrochloride... 

Preparation of 3-[5 -amino-(/Y-l-butyloxycarbonyl)- -pentanyl]-5-[(indol-3-yl) methyl]-imidazolidine 2,4-dione... 

Cases in which more than one tautomerizable substituent are present in the imidazole ring are common, but tautomerism studies of such compounds are less so. Work on the hydantoins (imidazolidine-2,4-diones) is not at all definitive UV and IR studies suggest the dioxo form (78), but evidence for the existence of other tautomeric structures (79,80) is not convincing (Scheme 26). ImidazoIidine-4,5-diones also exist as the dioxo forms. NMR studies show that the 2-benzyl derivatives must exist in solution as the NH form (81 R = H, Me), and the methoxy derivatives, similarly, are NH (82) rather than OH (83) derivatives (Scheme 26). 

Iinidazolidine-4,5-dione-2-thiones (26), also known as thioparabanic acids, can be prepared by beating thioureas with oxalyl chloride or diethyl oxalate. Cyanogen may also be used if the reactants are heated in the presence of acid. Stoffel and Ulrich and Sayigh have studied in detail the reaction of thioureas with oxalyl chloride and were able to isolate intermediate thiazolidine-4,5-diones (25) which on heating rearranged to the imidazolidine-4,5-dione-2-thiones (26). Thus, in the mechanism proposed by Stoffel, initial attack of the oxalyl chloride is on sulfur to form 24, which can cyclize to 25. Further heating then eauses rearrangement of 25 to 26. 

Z)-l-Acyl-3-methyl-5-(cyanomethylidene)imidazolidine-2,4-diones such as 807 readily undergo 1,3-dipolar cycloadditions with various 1,3-dipoles. The final products depend both on the nature of the dipoles and the dipolarophiles. Thus, spirohydantoins 808 and 809 are formed under neutral conditions with diazomethane or a nitrile oxide whereas further isomerization occurs under either basic or acidic conditions leading to acylureas such as 811 via 810 (Scheme 200) <2001HCA3403>. 

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