6777-06-6Relevant academic research and scientific papers
Highly efficient dialkylphosphate-mediated syntheses of hydantoins and a bicyclohydantoin under solvent-free conditions
Kumar, Vinod,Rana, Hemlata,Sankolli, Ravish,Kaushik
experimental part, p. 6148 - 6151 (2011/11/30)
Diversely substituted hydantoins have been synthesized by new strategy from cyanamide based precursor, that is, methyl N-cyano-N-alkyl/arylaminoacetate. Dialkylphosphates were employed as the mild reagent to hydrolyze and cyclize the substrate in one step to give quantitative yields of the desired products. Syntheses of multivalent hydantoins viz bis-hydantoin, bicyclohydantoin have potentially widened the scope and applicability of the present method. Solvent-free conditions and very easy work-up procedure make the reaction convenient and eco-friendly. Single crystal structures of some of the representative compounds are also reported.
An efficient approach for the synthesis of N-1 substituted hydantoins
Kumar, Vinod,Kaushik,Mazumdar, Avik
experimental part, p. 1910 - 1916 (2009/04/04)
An efficient three-step route for the synthesis of N-1 alkyl/aryl- substituted hydantoins was developed from inexpensive commercially available substrates. The reaction of amines with cyanogen bromide takes place to give monoalkyl/aryl cyanamides. This on treatment with methyl bromoacetate in the presence of sodium hydride in tetrahydrofuran affords methyl N-cyano-N-alkyl/arylaminoacetate, which undergoes hydrolysis and cyclization in the presence of 50% H2SO4 to afford N-1 substituted hydantoins in very good-to-excellent yields. Wide varieties of final products having primary, secondary, tertiary, and aryl substituents at the N-1 position were successfully synthesized by this method. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Synthesis of new chiral mono-, di-, tri-, and tetraalkylglycolurils
Kravchenko,Sigachev,Maksareva,Gazieva,Trunova,Lozhkin,Pivina,Il'in,Lyssenko,Nelyubina,Davankov,Lebedev,Makhova,Tartakovsky
, p. 691 - 704 (2007/10/03)
Two general procedures were developed for the synthesis of chiral N-mono-, N, N′-di-, N, N′ N″-tri-, and N, N′, N″, N′″-tetraalkylglycolurils based on the reactions of 4,5-dihydroxy-imidazolidin-2-ones or glyoxal with one or two moles of alkylureas, respectively, by acid catalysis. The reactions of N-monoalkyl- and N, N′-dialkylureas with glyoxal proceed regioselectively. The mechanism of these reactions was suggested and partly confirmed by quantum-chemical calculations and experimental data. The enantiomeric separation of some chiral glycolurils by chiral-phase HPLC was carried out for the first time.
