Abstract
The α-ureidoalkylation of N-(hydroxyalkyl)ureas (ureido alcohols) with 1,3-H2- and 1,3-Me2-4,5-dihydroxyimidazolidin-2-ones was systematically studied. The yields of glycolurils decrease both in going from 1,3-H2- to 1,3-Me2-4,5-dihydroxyimidazolidin-2-one and with increasing length (or with branching) of the hydroxyalkyl chain in ureido alcohols. The optimal reaction time for ureido alcohols is 1 h. The X-ray diffraction study showed that 2-(2-hydroxy-1,1-dimethylethyl)glycoluril crystallizes as a conglomerate. The enantiomeric analysis of 2-(2-hydroxyethyl)glycoluril was carried out by chiral-phase HPLC.
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Dedicated to Academician O. N. Chupakhin on the occasion of his 75th birthday.
For Part 1, see Ref. 1.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1229–1233, June, 2009.
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Kravchenko, A.N., Sigachev, A.S., Belyakov, P.A. et al. 4,5-Dihydroxyimidazolidin-2-ones in α-ureidoalkylation of N-carboxy-, N-hydroxy-, and N-aminoalkylureas 2. α-Ureidoalkylation of N-(hydroxyalkyl)ureas. Russ Chem Bull 58, 1264–1269 (2009). https://doi.org/10.1007/s11172-009-0165-5
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DOI: https://doi.org/10.1007/s11172-009-0165-5