4,5-Dihydroxyimidazolidin-2-ones in the α-ureidoalkylation reaction of N-(carboxyalkyl)-, N-(hydroxyalkyl)-, and N-(aminoalkyl)ureas 1. α-Ureidoalkylation of N-(carboxyalkyl)ureas View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2009-02

AUTHORS

A. N. Kravchenko, K. A. Lyssenko, I. E. Chikunov, P. A. Belyakov, M. M. Il’in, V. V. Baranov, Yu. V. Nelyubina, V. A. Davankov, T. S. Pivina, N. N. Makhova, M. Yu. Antipin

ABSTRACT

The α-ureidoalkylation of N-(carboxyalkyl)ureas (ureido acids) with 1,3-H2s-, 1,3-Me 2s-, and 1,3-Et2s-4,5-dihydroxyimidazolidin-2-ones was systematically studied. The yields of glycolurils were shown to decrease both in going from 1,3-H2s- to 1,3-Me2s- and 1,3-Et2s- 4,5- dihydroxyimidazolidin-2-ones and with elongation and branching of the carboxyalkyl chain in the ureido acids under study. The optimal reaction time for most of ureido acids is 3 h. The reaction mechanism was proposed. This mechanism was partially confirmed by quantum chemical methods and 1H NMR spectroscopy. Crystals of a number of the newly synthesized compounds were studied by X-ray diffraction, and two new conglomerates were found. A method was developed for the enantiomeric analysis of some racemic N-(carboxyalkyl)-glycolurils by chiral-phase HPLC. More... »

PAGES

395-405

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s11172-010-0022-6

DOI

http://dx.doi.org/10.1007/s11172-010-0022-6

DIMENSIONS

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