Regioselective synthesis of 2,8-disubstituted 1,5-diphenylglycolurils

Баранов, В. В.; Antonova, M. M.; Nelyubina, Yulia V.; Kolotyrkina, N. G.; Zanin, I. E.; Кравченко, Ангелина Н.; Махова, Нина Н.

doi:10.1016/j.mencom.2014.04.017

Cited by 14 publications

(8 citation statements)

References 26 publications

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“…Our motivation for choosing these reactions arose from our recent synthesis of imidazoxazoles 5a-c by simple reactions of (4S*,5R*)-1, 3-dialkyl-4,5-dihydroxy-4,5-diphenylimidazolidin-2-(thi)ones (6а,b and 7а) with potassium thiocyanate and acetic acid (Scheme 1). 7 The mechanism of the formation of compounds 5a-c was reported in our previous communication.…”

mentioning

confidence: 80%

“…8 Imidazolinones 9a-e were prepared by using a simple approach, starting from ureas 10а-e and benzoin (2-hydroxy-1,2-diphenylethanone; 11) (Table 1, entries 1-5). 9 Compounds 9f-h were prepared from the corresponding imidazole oxides 12а-с (entries 6-8). 10 5-Hydroxy-1-methyl-4,5-diphenyl-1,5-dihydro-2H-imidazol-2-one (8а) was used as a model compound to develop a procedure for the synthesis of imidazothiazole 13а.…”

Section: Letter Syn Lettmentioning

confidence: 99%

“…10 5-Hydroxy-1-methyl-4,5-diphenyl-1,5-dihydro-2H-imidazol-2-one (8а) was used as a model compound to develop a procedure for the synthesis of imidazothiazole 13а. Under the conditions used for the formation of imidazoxazoles 5a-c, 7 condensation of potassium thiocyanate with imidazolone 8a in the presence of acetic acid gave the imidazothiazole 13a in 35% yield (Table 2, entry 1). Methyl ether 14 11 proved to be the second and major product of this reaction (entry 1); complete conversion of imidazolone 8a into imidazothiazole 13а occurred only after five hours (entry 2).…”

Section: Letter Syn Lettmentioning

confidence: 99%

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Novel Method for the Synthesis of Substituted Imidazothiazolones

Кравченко

Antonova

Баранов

et al. 2015

Synlett

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Table of Contents I. General S3 II. General Procedure for the synthesis of 1-substituted 5-hydroxy-4,5-diphenyl-1H-imidazol-2(5H)-ones 8a-h S3 III. General procedure for the synthesis of 1-substituted 4,5-diphenyl-1Himidazol-2(3H)-ones 9a-e S5 IV. Procedure for the synthesis of 3-(2-oxo-4,5-diphenyl-2,3-dihydro-1H-imidazol-1-yl)propyl acetate 9g S6 V. General Procedure for the Synthesis of 1-substituted 5-hydroxy-4,5-diphenyl-1H-imidazol-2(5H)-ones 13a-h. S7 VI. Procedure for the Synthesis of 5-methoxy-1-methyl-4,5-diphenyl-1H-imidazol-2(5H)-one 14 S9 VII. Procedure for the synthesis of (4R*,5S*)-4,5-dihydroxy-1-methyl-4,5diphenylimidazolidin-2-one 15 S10 VIII. 1 Hand 13 C-NMR spectra of compounds 8,9,13-15 S11 IX. X-Ray Diffraction Data S30 X. Powder X-ray Diffraction Data. S32 XI. References S34 S 3 I. General All reagents were used directly from commercial suppliers without further purification. Melting points were determined on a Sanyo Gallenkamp apparatus. 1 H and 13 C NMR were recorded at 23 to 29 °C on a Bruker AC200, Bruker AM300, and Bruker DRX500 spectrometers using TMS as internal standard. High-resolution mass spectrs (HRMS) were obtain using a Bruker mikrOTOF II focus spectrometer (ESI). Mass spectra were measured on a MS 30 spectrometer. Elemental analyses were carried out with a Perkin-Elmer 2400 CHN Analyzer and Euro EA Elemental Analyzer. 1-Substituted 4,5-diphenyl-1H-imidazol-2(3H)-ones 9a-e 1 , 9f-h 2 , ureas 10b,d,e 3 and 1-substituted 4,5-diphenyl-1H-imidazole 3-oxide 12a,b 2 and 12c 4 were prepared according to the standard procedure. II. General Procedure for the synthesis of 1-substituted 5-hydroxy-4,5-diphenyl-1Himidazol-2(5H)-ones 8a-h 63% HNO 3 (5 mL) was added dropwise to a suspension of corresponding 1-substituted 4,5diphenyl-1H-imidazol-2(3H)-ones 9a-h (4 mmol) in MeCN (25 mL). The reaction was monitored by the dissolution of the precipitated 9a-h and by the change in color of solution. The reaction mixture was extracted with a 1:1 CHCl 3 /H 2 O mixture, the chloroform layer was evaporated, and the products 8a-h was rubbed with Et 2 O. 5-Hydroxy-1-methyl-4,5-diphenyl-1H-imidazol-2(5H)-one 8a Yield 0.94 g (88%), white powder, mp 222-224°С. 1 H NMR spectrum, δ, ppm;

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mentioning

confidence: 80%

Section: Letter Syn Lettmentioning

confidence: 99%

Section: Letter Syn Lettmentioning

confidence: 99%

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Novel Method for the Synthesis of Substituted Imidazothiazolones

Кравченко

Antonova

Баранов

et al. 2015

Synlett

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“…All reagents were purchased from commercial sources and used without treatment, unless otherwise indicated. Starting compounds 4 1 , 5 1 ,7 2 , 8b-d 3 , 9a-c, 1 10a-d 4 , were synthesized according to the literature. The 1 H NMR and 13 C NMR spectra were recorded on Bruker AM300 (300.13 MHz and 75.5 MHz, respectively) spectrometer using DMSO-d6 as solvent.…”

Section: General Informationmentioning

confidence: 99%

Direct Synthesis of 1-Alkyl-6-hydroxyalkyl-3a,6a-diphenylglycolurils from 1-Alkylimidazolinones and Their Cyclic Analogues

Баранов

Antonova

Kolotyrkina

et al. 2018

Synlett

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Two methods for the direct synthesis of previously inaccessible 1-alkyl-6-(hydroxyalkyl)-3a,6a-diphenylglycolurils have been developed as a result of a study of novel cyclocondensations of 1-alkylureas with tetrahydroimidazooxazolones, tetrahydroimidazooxazinones and 1-(hydroxyalkyl)ureas with 1-substituted imidazolinones. A mechanism to rationalize the highly regioselective formation of the target glycolurils is proposed.

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“…It is known that tetrahydroimidazo [4,5-d]imidazole-2,5(1H,3H)-diones (glycolurils) are capable of forming supramolecular assemblies and supermolecules of varying complexity upon crystallization from different solvents [9][10][11][12][13][14][15][16][17][18][19][20][21], which can lead to spontaneous resolution of racemates into enantiomers (conglomerate formation) [22][23][24][25][26]. Some glycolurilcarboxylic acids [16,17,20,21,24,25] also have such properties (Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Crystal Structures of Novel Glycoluryl Carboxylic Acids Conglomerates

Баранов¹,

Vol’khina²,

Кравченко³

2021

Preprint

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The two novel conglomerats were obtained by crystallization of racemic (S)-2-((3aS,6aR)- and (R)-2-((3aR,6aS)-2,5-dioxohexahydroimidazo[4,5-d]imidazole-1(2H)-yl)-3-methylbutanoic acids (racemate I), (R)-2-(3aR,6aR)- and (S)-2-((3aS,6aS)-4,6-dimethyl-2,5-dioxohexahydroimidazo[4,5-d]imidazole-1(2H)-yl)pentanoic acids (racemate II), which were synthesized by highly diastereoselective condensation of 4,5-dihydroxyimidazolidine-2-ones with racemic ureido acids for the first time. The differences in the molecular geometry of I and II are studied by X-ray diffraction that showed them to crystallize as conglomerates in non-centrosymmetric space groups Pna21 and P212121, respectively.

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Regioselective synthesis of 2,8-disubstituted 1,5-diphenylglycolurils

Cited by 14 publications

References 26 publications

Novel Method for the Synthesis of Substituted Imidazothiazolones

Novel Method for the Synthesis of Substituted Imidazothiazolones

Direct Synthesis of 1-Alkyl-6-hydroxyalkyl-3a,6a-diphenylglycolurils from 1-Alkylimidazolinones and Their Cyclic Analogues

Synthesis and Crystal Structures of Novel Glycoluryl Carboxylic Acids Conglomerates

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