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
A N Kravchenko
1
,
K.A. Lyssenko
2
,
I E Chikunov
1
,
P A Belyakov
1
,
M. M. Il’in
2
,
V.V. Baranov
1
,
Yu V Nelyubina
2
,
V. A. Davankov
2
,
T. S. Pivina
1
,
N N Makhova
1
,
M. Yu. Antipin
2
Publication type: Journal Article
Publication date: 2009-02-01
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
General Chemistry
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.
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Kravchenko A. N. et al. 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 // Russian Chemical Bulletin. 2009. Vol. 58. No. 2. pp. 395-405.
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Kravchenko A. N., Lyssenko K., Chikunov I. E., Belyakov P. A., Il’in M. M., Baranov V., Nelyubina Yu. V., Davankov V. A., Pivina T. S., Makhova N. N., Antipin M. Y. 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 // Russian Chemical Bulletin. 2009. Vol. 58. No. 2. pp. 395-405.
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TY - JOUR
DO - 10.1007/s11172-010-0022-6
UR - http://link.springer.com/10.1007/s11172-010-0022-6
TI - 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
T2 - Russian Chemical Bulletin
AU - Kravchenko, A N
AU - Lyssenko, K.A.
AU - Chikunov, I E
AU - Belyakov, P A
AU - Il’in, M. M.
AU - Baranov, V.V.
AU - Nelyubina, Yu V
AU - Davankov, V. A.
AU - Pivina, T. S.
AU - Makhova, N N
AU - Antipin, M. Yu.
PY - 2009
DA - 2009/02/01
PB - Springer Nature
SP - 395-405
IS - 2
VL - 58
SN - 1066-5285
SN - 1573-9171
ER -
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@article{2009_Kravchenko,
author = {A N Kravchenko and K.A. Lyssenko and I E Chikunov and P A Belyakov and M. M. Il’in and V.V. Baranov and Yu V Nelyubina and V. A. Davankov and T. S. Pivina and N N Makhova and M. Yu. Antipin},
title = {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},
journal = {Russian Chemical Bulletin},
year = {2009},
volume = {58},
publisher = {Springer Nature},
month = {feb},
url = {http://link.springer.com/10.1007/s11172-010-0022-6},
number = {2},
pages = {395--405},
doi = {10.1007/s11172-010-0022-6}
}
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MLA
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Kravchenko, A. N., et al. “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.” Russian Chemical Bulletin, vol. 58, no. 2, Feb. 2009, pp. 395-405. http://link.springer.com/10.1007/s11172-010-0022-6.