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

被引：15

作者：

Kravchenko, A. N. ^{[1
]}

Lyssenko, K. A. ^{[2
]}

Chikunov, I. E. ^{[1
]}

Belyakov, P. A. ^{[1
]}

Il'in, M. M. ^{[2
]}

Baranov, V. V. ^{[1
]}

Nelyubina, Yu. V. ^{[2
]}

Davankov, V. A. ^{[2
]}

Pivina, T. S. ^{[1
]}

Makhova, N. N. ^{[1
]}

Antipin, M. Yu. ^{[2
]}

机构：

[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia

[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2009年 / 58卷 / 02期

关键词：

glycolurils; 4,5-dihydroxyimidazolidin-2-ones; N-(carboxyalkyl)ureas (ureido acids); racemates; conglomerates; enantiomers; quantum chemical calculations; X-ray diffraction and enantiomeric analysis; SPONTANEOUS RESOLUTION; GLYCOLURIL;

D O I：

10.1007/s11172-010-0022-6

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The alpha-ureidoalkylation of N-(carboxyalkyl)ureas (ureido acids) with 1,3-H-2 (s-), 1,3-Me (2) (s-), and 1,3-Et-2 (s-)4,5-dihydroxyimidazolidin-2-ones was systematically studied. The yields of glycolurils were shown to decrease both in going from 1,3-H-2 (s-) to 1,3-Me-2 (s-) and 1,3-Et-2 (s-) 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 H-1 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.

引用

页码：395 / 405

页数：11

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