5395-50-6Relevant articles and documents
Reaction of N-alkylglycolurils with electrophilic reagents
Kravchenko,Sigachev,Gazieva,Maksareva,Trunova,Chegaev,Lyssenko,Lyubetsky,Struchkova,Il'in,Davankov,Lebedev,Makhova,Tartakovsky
, p. 365 - 376 (2006)
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.
A study of products of tetrakis(hydroxymethyl)glycoluril dehydroxymethylation in aqueous solutions
Panshina, S. Yu.,Ponomarenko,Bakibaev,Sidelnikov,Kurgachev,Malkov,Khlebnikov,Tashenov
, p. 140 - 147 (2021/03/02)
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.
Efficient method for the cycloaminomethylation of glycoluril
Wingard, Leah A.,Johnson, Eric C.,Sabatini, Jesse J.
supporting information, p. 1681 - 1682 (2016/04/04)
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.
HERBICIDE COMPOSITION COMPRISING CLOMAZONE AND USE
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Page/Page column 14, (2014/10/29)
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.
