H 99 Interaction of 5-methoxy-1,2,4-triazines with Urea: a New Way to the Synthesis of Azapurine Derivatives [Text] : доклад, тезисы доклада / D. G. Beresnev, G. L. Rusinov, O. N. Chupakhin, H. Neunhoeffer // International Memorial I.Postovsky Conference on Organic Chemisty, Ekaterinburg, March 17-20, 1998 : program and abstracts. - Ekaterinburg, 1998. - P50 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
O-57 One-step solvent-free synthesis of fluoroalkyl-substituted 4-hydroxy-2-oxo(thioxo)hexahydropyrimidines in the presence of 1-butyl-3-methylimidazolium tetrafluoroborate [Electronic resource] / E. S. Putilova, N. A. Troitskii, S. G. Zlotin, O. G. Khudina, Ya. V. Burgart, V. I. Saloutin, O. N. Chupakhin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2006. - Vol. 42, № 9. - P1392-1395 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A convenient procedure has been developed for the synthesis of fluoroalkyl-substituted 6-aryl-4-hydroxy-2-oxo-(thioxo)hexahydropyrimidine derivatives by three-component condensation of fluorinated ?-dicarbonyl compounds with aromatic aldehydes and urea or thiourea in the absence of a solvent using 6 mol % of 1-butyl-3-methylimidazolium tetrafluoroborate as catalyst. \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2006, 42 (9), 1392.pdf |
R 30 Reactions of alkyl 2-benzylidene-2-polyfluoroacylacetates with N,N-dinucleophiles [Electronic resource] / M. V. Pryadeina, Ya. V. Burgart, M. I. Kodess, V. I. Saloutin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 6. - P1261-1266. - Библиогр. : с. 1266 (16 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Alkyl 2-benzylidene-2-polyfluoroacylacetates react with urea and thiourea to yield 5-ethoxycarbonyl-4-fluoroalkyl-4-hydroxy-6-phenylhexahydropyrimidin-2-ones and -2-thiones and with guanidine sulfate to form 2-amino-5-ethoxycarbonyl-4-fluoroalkyl-6-phenyl-1,6-dihydropyrimidines and 3,6-diethoxycarbonyl-2,7-difluoroalkyl-4,5-diphenyl-4,5-dihydro-1H-pyrido[1,2-a]pyrimidines, and they react with phenylhydrazine to afford 4-alkoxycarbonyl-3-fluoroalkyl-3-hydroxy-1,5-diphenylpyrazolidines. Hydrazine hydrate catalyzes the formation of 3,5-diethoxycarbonyl-2,6-difluoroalkyl-2,6-dihydroxy-4-phenyltetrahydropyrans. When treated with anhydrous hydrazine and o-phenylenediamine, these esters cleave to form the products of condensation of fluoroacyl ester and benzaldehyde with diamines. \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (6), 1261-1266.pdf |
S 98 Syntheses of novel 4-polyfluoroalkyl-substituted 5,6-oligomethylene pyrimidines [Text] / D. V. Sevenard, O. G. Khomutov, O. V. Koryakova, V. V. Sattarova, M. I. Kodess, J. Stelten, I. Loop, E. Lork, K. I. Pashkevich, G. -V. Roeschenthaler // Synthesis. - 2000. - № 12. - P1738-1748 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 2-Acylcycloalkanones having polyfluoroalkyl groups react with guanidine, urea, thiourea, methylisothiourea, benzamidine, guanylthiourea, dicyanodiamide, and trifluoroacetylurea by Lewis-acid catalysis to form the corresponding 5,6-oligomethylene pyrimidines. A decrease in the yields along with increase of polyflyoroalkyl substituent length in the molecule of the starting 1,3-diketone was observed in the case of reagents with lower nucleophilicity (urea, thiourea, dicyanodiamide). The pyrimidines obtained from aromatic aldehydes showed E-configuration with respect to the arylidene double bond. Tautomeric structures as a function of the substituent in 2 position in the pyrimidine ring both in liquid and solid state were investigated by X-ray diffraction, IR and NMR spectroscopy. \\\\expert2\\nbo\\Synthesis\\2000, № 12. p.1738.pdf |
B 57 Biginelli condensations of fluorinated 3-oxo esters and 1,3-diketones [Text] / V. I. Saloutin, Ya. V. Burgart, O. G. Kuzueva, C. O. Kappe, O. N. Chupakhin // Journal of Fluorine Chemistry. - 2000. - Vol. 103, № 3. - P17-23 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Condensation of fluorinated 3-oxo esters or 1,3-diketones with benzaldehyde and (thio)urea results in the diastereoselective formation of 4-fluoroalkyl-4-hydroxy-2-oxo(thioxo)-6-phenyl-hexahydropyrimidine-5-carboxylates from which by dehydration under acidic conditions the corresponding 6-fluoroalkyl-2-oxo(thioxo)-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylates were obtained. Under the same conditions, hexafluoroacetylacetone furnishes 4,6-dihydroxy-4,6-di(trifluoromethyl)-hexahydropyrimidin-2-one. Some further reactions of these pyrimidine derivatives leading to fused heterocycles are described.???? |
S 98 Synthesis of fluorine containing glycolurils and oxazolines from oxides of internal perfluoroolefins [Text] / L. V. Saloutina, A. Ya. Zapevalov, V. I. Saloutin, P. A. Slepukhin, M. I. Kodess, O. N. Chupakhin // Journal of Fluorine Chemistry. - 2009. - Vol. 130, № 10. - P853-860 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): OXIDES OF INTERNAL PERFLUOROOLEFINS -- 1,5-bIS(PERFLUOROALKYL)TETRAAZABICYCLO[3.3.0]OCTANE-3,7-D Аннотация: The reaction of oxides of internal perfluoroolefins 1–3 with urea gave two kinds of novel fluorine containing N-heterocyclic compounds depending on the solvent nature: 1,5-bis(perfluoroalkyl)tetraazabicyclo[3.3.0]octane-3,7-diones 4a–c and 2-amino-5-fluoro-4,5-bis(perfluoroalkyl)-4,5-dihydrooxazol-4-ols 7a–d. Use of polar dimethylsulfoxide, N,N-dimethylacetamide and acetonitrile afforded glycolurils 4a–c in moderate yields. In dioxane, unexpected cyclization occurred resulting in oxazolines 7a–d in high yields. A similar reaction of oxiranes 2, 3 with urea in aqueous dioxane gave mixtures of 4,5-dihydroxy-4,5-bis(perfluoroalkyl)imidazolidine-2-ones 9b, c, glycolurils 4b, c and oxazolines 7b–d. The molecular structure of trans-isomers of oxazoline 7b and imidazolidine 9b has been established by X-ray crystallography?? \\\\Expert2\\nbo\\Journal of Fluorine Chemistry\\2009, V. 130, P. 853.pdf |
F 70 Fluorocontaining 1,3-Dicarbonyl Compounds in the Synthesis of Pyrimidine Derivatives ?? [Electronic resource] / Ya. V. Burgart, O. G. Kuzueva, M. V. Pryadeina, C. O. Kappe, V. I. Saloutin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2001. - Vol. 37, № 6. - P869-880 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Hexafluoroacetylacetone reacts with urea (thiourea) to yield respectively 4,6-bis(hydroxy)-4,6-bis(trifluoromethyl)hexahydropyrimidin-2-one(thione). The dehydration of the products and also reaction of nonsymmetrical fluoroalkyl-containing 1,3-diketones with urea (thiourea) afford substituted pyrimidines. The condensation of fluorinated 3-oxoesters and 1,3-diketones with benzaldehyde and urea (thiourea) results in 5-alkoxycarbonyl(acyl)-4-hydroxy-2-oxo(thioxo)-6-phenyl-4-fluoroalkylhexahydropyrimidines that on dehydration furnish 5-alkoxycarbonyl(acyl)-2-oxo(thioxo)-4-phenyl-6-fluoroalkyltetrahydropyrimidines. Ethyl 7-nonafluorobutyl-5-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidine-6-carboxylate hydrobromide forms in reaction of dibromoethane with ethyl ether of 2-thioxo-4-phenyl-6-nonafluorobutyltetrahydropyrimidine \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2001, 37 (6), 869.pdf |
S 45 Selection of catalytic systems for biometric sensors [] / A. Kozitsina, S. Dedeneva, Kh. Brainina, V. N. Charushin, O. N. Chupakhin, G. L. Rusinov // The 7th Workshop on Biosensors and Bioanalytical - Techniques in Environmental and Clinical Analysis, Kusadasi, Turkiye, 10-14 Sept. 2006 г. - 2006. - 115 (PP 43). - Библиогр.: с. 115 (1 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ |
R 30 Reactions of internal perfluoroolefin oxides with urea [Electronic resource] / L. V. Saloutina, A. Ya. Zapevalov, V. I. Saloutin, M. I. Kodess, P. A. Slepukhin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2009. - Vol. 45, № 6. - P865-871. - Bibliogr. : p. 871 (19 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): OXIDES -- PERFLUOROOLEFIN OXIDES -- UREA -- HETEROCYCLES Аннотация: Internal perfluoroolefin oxides reacted with urea to give, depending on the solvent nature, two types of new fluorine-substituted nitrogen-containing heterocycles. 1,5-Bis(perfluoroalkyl)tetraazabicyclo[3.3.0]octane-3,7-diones were formed in dimethyl sulfoxide, N,N-dimethylacetamide, and acetonitrile, while the reaction in dioxane resulted in the formation of unexpected products, 2-amino-5-fluoro-4,5-bis(perfluoroalkyl)-4,5-dihydrooxazol-4-ols, existing mainly as trans isomers. trans Orientation of perfluoroalkyl substituents in these compounds was determined by analysis of 19F-19F spin-spin coupling constants in the 19F NMR spectra. The molecular structure of trans-2-amino-5-fluoro-4,5-bis(trifluoromethyl)-4,5-dihydrooxazol-4-ol was studied by X-ray analysis. \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2009, 45 (6), 865.pdf |
E 43 Electrochemical sensor based on metal-containing receptors for urea measurements [Text] : доклад, тезисы доклада / A. Kozitsina [и др.] // International Congress on Analytical Sciences "ICAS - 2006",M., June 25-30 2006 : book of abstracts. - М., 2006. - Vol. 1. - P291 : табл. - Bibliogr. : p. 291 (1 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ |
2,3-Epoxyperfluoro-2-methylpentane in reactions with urea and thiourea [Electronic resource] / T. I. Filyakova, V. I. Saloutin, A. Ya. Zapevalov, P. A. Slepukhin, M. I. Kodess, V. I. Saloutin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2011. - Vol. 47, № 5. - P650-658 : рис., табл. - Bibliogr. : p. 658 (24 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 2,3-Epoxyperfluoro-2-methylpentane reacts with thiourea in protic (methanol, 2-propanol) and aprotic (dioxane) solvents, and also with urea in acetonitrile affording unexpected products: 1-(2,2,3,3,3-pentafluoropropionyl)-2-(2,2,2-trifluoro-1-trifluoro-methylethyl)isothiourea, and 1-(2,2,3,3,3-pentafluoropropionyl)-3-(2,2,2-trifluoro-1-trifluoro-methylethyl)urea respectively that result from the rearrangement of the intermediately formed ketone in the process of the intramolecular “haloform” cleavage. At the same time in dioxane the 2,3-epoxyperfluoro-2-methylpentane reacts with urea with the formation of a heterocyclic compound, 2-amino-4-pentafluoroethyl-5,5-bis(trifluoromethyl)-4,5-dihydrooxazol-4-ol. From 1-(2,2,3,3,3-pentafluoropropionyl)-2-(2,2,2-trifluoro-1-trifluoromethylethyl)isothiourea and Cu(OAc)2 a stable fluorine-containing chelate complex was obtained \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2011, 47 (5), 650-658.pdf |
S 98 Synthesis of fluorine containing N-heterocycles using oxides of terminal perfluoroolefins and urea / L. V. Saloutina, A. Ya. Zapevalov, M. I. Kodess, P. A. Slepukhin, V. I. Saloutin, O. N. Chupakhin // Journal of Fluorine Chemistry. - 2012. - Vol.139. - С. 16-22 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): Me2SO -- PERFLUOROOLEFINS -- UREA Аннотация: The reaction of octafluoro-1,2-epoxybutane (1) with urea in Me2SO, aqueous Me2SO, aqueous dioxane, aqueous acetonitrile and of hexadecafluoro-1,2-epoxyoctane (2) with urea in aqueous Me2SO gave perfluoroalkylhydantoins – 5-hydroxy-5-pentafluoroethylimidazolidine-2,4-dione (4a) (yield 40–42%) and 5-hydroxy-5-tridecafluorohexylimidazolidine-2,4-dione (4b) (yield 54%), respectively. Use of dioxane and acetonitrile in the reaction of oxiranes 1, 2 with urea led to unexpected heterocyclic products – perfluoroalkyloxazoles 7a, b (yield 11–82%). Perfluoroalkyl containing allantoin – 5-tridecafluorohexyl-5-ureidoimidazolidine-2,4-dione (3b) (yield 19%) and polyfluoroalkyl containing urea–(2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoro-1-hydroxyheptyl)urea (6b) (yield 46%) have been first obtained by the reaction of oxirane 2 with urea in Me2SO and aqueous Me2SO, respectively \\\\Expert2\\nbo\\Journal of Fluorine Chemistry\\2012, v. 139, p.16.pdf |
S 98 Synthesis of fluorine-containing allantoins, hydantoins, and oxazolones from terminal perfluoroolefin oxides and urea / L. V. Saloutina, A. Ya. Zapevalov, M. I. Kodess, V. I. Saloutin, O. N. Chupakhin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2012. - Vol.48, №3. - С. 387-393 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ALLANTOINS -- HYDANTOINS -- OXAZOLONES Аннотация: 1,2-Epoxyoctafluorobutane reacted with urea in DMSO and aqueous DMSO, dioxane, and acetonitrile to give 40–42% of 5-hydroxy-5-pentafluoroethylimidazolidine-2,4-dione. 5-Hydroxy-5-tridecafluorohexylimidazolidine-2,4-dione was formed in 54% yield in analogous reaction of 1,2-epoxytridecafluorooctane with urea in aqueous DMSO. The reactions of 1,2-epoxyoctafluorobutane and 1,2-epoxytridecafluorooctane with urea in anhydrous dioxane and acetonitrile unexpectedly afforded heterocyclization products, 2-amino-5-fluoro-5-perfluoroalkyloxazol-4(5H)-ones (yield 11–82%). Fluorine-containing allantoin, 5-tridecafluorohexyl-5-ureidoimidazolidine-2,4-dione (yield 19%), and N-(1-hydroxy-2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptyl)-urea (yield 46%) were synthesized for the first time by reaction of 1,2-epoxytridecafluoroctane with urea in DMSO and aqueous DMSO \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2012, 48 (3), 387-393.pdf |
K 96 Kuznetsov, V. A. Synthesis of epsilon-caprolactone with stable hydrogen peroxide adducts / V. A. Kuznetsov, M. G. Pervova, Yu. G. Yatluk // Russian Journal of Applied Chemistry. - 2013. - Vol.86, №2. - С. 176-181. - Библиогр.: с. 181 (16 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CYCLOHEXANONE -- E-CAPROLACTONE -- HEXAFLUOROISOPROPANOL Аннотация: Oxidation of cyclohexanone to ɛ-caprolactone with stable industrially manufactured hydrogen peroxide derivatives: adduct with urea (urea hydrogen peroxide), sodium perborate, sodium percarbonate (Persol), magnesium monoperphthalate (Dismozon) was studied. Oxidation with urea hydrogen peroxide is the most efficient in hexafluoroisopropanol in the case of preliminary removal of urea in the form of an oxalate. Oxidation with sodium perborate and percarbonate provides high yields in trifluoroacetic acid. The lowest cost process consists in interaction with sodium monoperphthalate (Persol and phthalic anhydride) in an aqueous medium \\\\expert2\\NBO\\Russian Journal of Applied Chemistry\\2013, v. 86, N 2, p.176.pdf |
S 90 Study of oligomeric compounds of Urea-fotmaldehyde concentrate by ESI MS, IR and NMR spectroscopy / S. Y. Men'shikov, I. N. Ganebnuikh, M. S. Valova, L. S. Molochnikov // European Polymer Congress, Pisa, June 16-21 2013 : book of abstracts . - Pisa, Italy, 2013. - P2-107 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SPECTROSCOPY -- OLIGOMERIZATION PRODUCTS -- NMR SPECTRA |
S 90 Study of oligomeric compounds of urea-formaldehyde concentrate by ESI MS, IR and NMR spectroscopy / S. Y. Men'shikov, I. N. Ganebnuikh, M. S. Valova, L. S. Molochnikov // European Polymer Congress, Pisa, June 16-21 2013 : book of abstracts . - Pisa, Italy, 2013. - С. 2-107 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): OLIGOMERIC COMPOUNDS -- UREA-FORMALDEHYDE -- NMR SPECTROSCOPY |
S 98 Synthesis of podands with dihydropyrimidine fragments based on polyethers with terminal acetoacetamide groups [Electronic resource] / E. S. Radionava, O. V. Fedorova, Yu. A. Titova, G. L. Rusinov, V. N. Charushin // Chemistry of Heterocyclic Compounds. - 2015. - Vol. 51, № 5. - С. 478-482. - Bibliogr. : p. 482 (19 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ACETOACETAMIDE-CONTAINING PODANDS -- DIHYDROPYRIMIDINE-CONTAINING PODANDS -- ACETYLKETENE Аннотация: Reactions of aliphatic aminopodands having different length of the polyether chain with acetoacetic ester and 2,2,6-trimethyl-4H-1,3-dioxin-4-one were studied. The interaction of aminopodands with acetoacetic ester in toluene upon sonication (60A degrees D) or heating (90A degrees D) gave podands with terminal aminocrotonate fragments. The use of dioxinone at the same temperature allowed to transform aminopodands into aliphatic acetoacetamide-containing podands. An asymmetric podand with 2-pyridone fragment was isolated as byproduct from the reaction of dioxinone with 1,5-diamino-3-oxapentane. A three-component Biginelli reaction of acetoacetamidecontaining podands with benzaldehyde and urea in the presence of catalytic amounts of polyphosphoric acid immobilized on nanosized TiO2-SiO2 oxide surface enabled the synthesis of podands with 1,4-dihydropyrimidin-2-(1De)-one fragments. \\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\2015, v.51, N 5, p. 478-482.pdf |
A 89 Asymmetric Biginelli Reaction Catalyzed by Silicon, Titanium and Aluminum Oxides [Electronic resource] / O. V. Fedorova, Yu. A. Titova, A. Yu. Vigorov, M. S. Toropova, O. A. Alisienok, A. Murashkevich, V. P. Krasnov, G. L. Rusinov, V. N. Charushin // Catalysis Letters. - 2016. - Vol.146, № 2. - С. 493-498 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): BIGINELLI REACTION -- PHENYLETHYLAMINE -- ALUMINUM OXIDES Аннотация: The asym. Biginelli reaction was investigated in the presence of N-[(2S,4R)-4-hydroxyprolyl]-(S)-1-phenylethylamine as chiral inducer and silicon, titanium or aluminum oxides (individual and mixed, bulk and nanosized) as heterogeneous catalysts. The synthesis of Et (4R)-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate from benzaldehyde, urea and Et acetoacetate has been described. It has been shown that all studied oxides improve chemo- and stereoselectivity of the Biginelli reaction. \\\\expert2\\nbo\\Catalysis Letters\\2016, v.146, p.493.pdf |
Urea-containing oligomers/polymers as chemosensors for visual detection of phosphate anions / V. A. Platonov, G. V. Zyryanov, I. S. Kovalev [et al.] // AIP Conference Proceedings. - 2021. - Vol. 2388, № 1. - Ст. 040004 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Isomeric urea-containing polymeric/oligomeric chemosensors for anions were prepared by means of interaction of isomeric diaminobihenyls with triphosgene. An intensive “turn-on” fluorescence response toward phosphate anion in solutions was observed. |
Transformations of 4,5-bis(trifluoromethyl)imidazolidin-2-one and its N-substituted analogous in reactions with N,N-dinucleophiles / L. V. Saloutina, A. Y. Zapevalov, M. I. Kodess [et al.] // AIP conference proceedings. - 2022. - Vol. 2390. - Ст. 020069 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CHEMICAL COMPOUNDS Аннотация: 4,5-Dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-one and its N-methyl(phenyl)-substituted analogous were synthesized by the reaction of perfluorobiacetyl with urea and methyl(phenyl)urea. Depending on a solvent nature and character of the substituent at N-atom of the imidazolidine, different trifluoromethyl-containing heterocycles were obtained in reactions of the imidazolidin-2-ones with thiosemicarbazide and guanidine carbonate: imidazothiazol, 1,2,4-triazines, and hydantoins. |