- Reaction of N-alkylglycolurils with electrophilic reagents
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The N-hydroxymethylation, N-acetylation, and N-acetoxymethylation of mono-, di-, and trialkylglycolurils by reaction with the electrophilic reagents formaldehyde and acetaldehyde have been studied. General methods have been developed for the preparation of mono-, di-, and tri-N-hydroxymethylglycolurils by treatment of differently substituted N-alkylglycolurils with formaldehyde (as hemiformal in methanol) and the synthesis of di-N-and tri-N-acetyl-or N-acetoxymethylglycolurils via the electrophilic substitution of hydrogen atoms for an acetyl group at the nitrogen or oxygen atoms in the hydroxymethyl groups of glycolurils using acetic anhydride. The regioselectivity of the reaction of the 2-t-Bu-and 2-c-C6H11-glycolurils with formaldehyde has been shown to yield a 4,6-di(hydroxymethyl) derivative. It was found that the hydroxymethylation of 2,4-and 2,6-dialkylglycolurils occurs regioselectively with a stoichiometric ratio of glycoluril to hemiformal and permits preparation of their mono-and dihydroxymethyl derivatives. The enantiomeric analysis of the obtained compounds has been carried out for the first time using HPLC on chiral phases. X-ray analysis has been carried out on the previously unreported racemic 2,6-diacetoxymethyl-4,8-dimethylglycoluril. 2006 Springer Science+Business Media, Inc.
- Kravchenko,Sigachev,Gazieva,Maksareva,Trunova,Chegaev,Lyssenko,Lyubetsky,Struchkova,Il'in,Davankov,Lebedev,Makhova,Tartakovsky
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- Glycoluril trimers: selective synthesis and supramolecular properties
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The first selective synthesis of glycolurll tri mers is described. Tri mers framed by o-xylylene walls represent new supramolecular hosts which are able to encapsulate bispyridinium ethylene and methylviologen guests In the solid state and aqueous solution.
- Stand, Marek,Hodan, Martin,Slndelar, Vladimir
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Read Online
- A study of products of tetrakis(hydroxymethyl)glycoluril dehydroxymethylation in aqueous solutions
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It was found that tetrakis(hydroxymethyl)glycoluril is unstable in aqueous solutions and undergoes stepwise dehydroxymethylation. The products of this process were identified by HPLC, 1D and 2D NMR spectroscopy. The main product of hydrolytic degradation at room temperature is tris(hydroxymethyl)glycoluril, which may be conditioned by the thermodynamic characteristics of the reaction. Further dehydroxymethylation to give di- and monohydroxymethyl glycoluril derivatives occurs under more severe conditions.
- Panshina, S. Yu.,Ponomarenko,Bakibaev,Sidelnikov,Kurgachev,Malkov,Khlebnikov,Tashenov
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p. 140 - 147
(2021/03/02)
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- Effect of glycoluril and its derivatives on the flame resistance and physico-mechanical properties of rubber
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The effect of bicyclic bisureas (glycolurils) and their derivatives functionalized with hydroxymethyl, halomethyl, and dimethoxyphoshorylmethyl groups on the flame resistance and physico-chemical properties of synthetic isoprene and divinyl rubbers was studied, and the procedures for preparing these agents were suggested. The rubbers with the addition of the synthesized bicyclic bisureas demonstrated satisfactory levels of flame resistance and physico-mechanical parameters.
- Sal’keeva,Bakibaev,Khasenova,Taishibekova, Ye. K.,Sugralina,Minaeva, Ye. V.,Sal’keeva
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p. 132 - 139
(2016/06/06)
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- Efficient method for the cycloaminomethylation of glycoluril
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The efficient method for the cycloaminomethylation of glycoluril to yield 2,6-ditert-butylhexahydro-1H,5H-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-4,8-dione is described. The material is synthesized employing water as the solvent, and is isolated by filtration. This is an improvement over the previous reported synthetic method, which relied on the use of samarium trichloride catalysis, as well as silica gel column chromatographic purification to obtain the target product.
- Wingard, Leah A.,Johnson, Eric C.,Sabatini, Jesse J.
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supporting information
p. 1681 - 1682
(2016/04/04)
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- CLOMAZONE COMPOSITION, ITS PREPARATION AND USE THEREOF
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A composition comprising an active ingredient, in particular Clomazone, contained within a microcapsule is provided, the microcapsules having a shell comprising a urea-formaldehyde resin. A method of preparing a microencapsulated composition comprising an encapsulated active ingredient, in particular Clomazone, is also provided, the method comprising: a) preparing a urea-formaldehyde prepolymer by the reaction of urea and formaldehyde; b) dispersing the active ingredient and a water insoluble liquid carrier in an aqueous phase to form an emulsion; and c) adding the urea-formaldehyde prepolymer to the emulsion and allowing the components thereof to react to form microcapsule walls at the interface of the dispersed organic phase and the aqueous phase, so as to encapsulate the organic phase.
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(2016/01/21)
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- HERBICIDE COMPOSITION COMPRISING CLOMAZONE AND USE
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There is provided a composition comprising clomazone encapsulated within microcapsules having a polymer wall comprising a cross-linked polyacetylene carbamide-polyurea. A preferred composition is prepared by providing a water imiscible organic phase comprising clomazone, one or more polyfunctional isocyanates and a cross-linking resin; providing an aqueous phase comprising one or more polyfunctional amines; dispersing the organic phase in the aqueous phase to form a dispersion of droplets of the organic phase in the aqueous; and allowing the formation of a polyacetylene carbamide-polyurea polymer at the interface of the dispersed organic phase and the aqueous phase. The composition is useful in the control of plant growth.
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(2014/10/29)
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