T 82 Transformations of 5-diazo derivatives of 1,3-dimethyl-6-hydrazinouracil - new synthetic approaches to novel pyrimidine-derivatives [Electronic resource] / Y. A. Azev, O. L. Guselnikova, O. N. Chupakhin // Mendeleev Communications. - 1994. - N 6. - P208-209 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 1,3-Dimethyl-6-hydrazinouracil 1 gives hydrazones 2 with the corresponding aldehydes. Heating of 6-hydrazinouracil 1 in ethanol in the presence of hyrochloric acid results in the formation of N1, N2-bis(1,3-dimethyl-2,6-dioxopyrimid-4-yl)hydrazine 3, which gives the diazo derivative 4 on treatment with 2,4-diazido-6-cyanomethoxy-s-triazine in DMSO in the presence of triethylamine et room temperature |
E 84 Ethyl cyanoacetate as 1,3-bifunctional reagent in the pyrimidine to pyridine ring transformations [Text] / O. N. Chupakhin, V. L. Rusinov, A. A. Tumashov, E. O. Sidorov, I. V. Karpin // Tetrahedron Letters. - 1992. - Vol. 33, N 25. - P3695-3696 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: By using of the double-labelled C(*)H(*)-CH2-COOEt compound it has been proved that transformation of 6-nitro-1,2,4-triazolo[1,5-a]pyrimidine into 2-triazolylamino-3-carbethoxy-5-nitropyridine proceeds with incorporation of the C-C-N fragment of ethyl cyanoacetate into the pyridine ring |
R 35 Regiospecific cleavage of a triazole or pyrimidine ring in nitrotriazolo[1,5-a]pyrimidones [Electronic resource] / V. V. Voronin, E. N. Ulomskii, V. L. Rusinov, O. N. Chupakhin // Mendeleev Communications. - 1999. - Vol. 9, N 5. - P200-201 . - ISSN 0959-9436 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
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.???? |
N 91 Nucleophilic substitution or dipolar 1,3-cycloaddition in reactions of cyanamide with 4-arylpyrimidine 1-oxides [Electronic resource] / A. M. Prokhorov, D. N. Kozhevnikov, V. L. Rusinov, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2003. - Vol. 52, № 5. - P1195-1197 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Pyrimidine 1-oxides with cyanamide afforded 2-ureidopyrimidines as the result of the nucleophilic substitution of hydrogen, whereas the formation of similar 2-trichloroacetylaminopyrimidines occurs as dipolar 1,3-cycloaddition of the same oxides to trichloroacetonitrile under much more drastic conditions and in lower yields?? \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2003, 52 (5), 1195.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 98 Synthesis of derivatives of pyrazolo[1,5- a ]pyrimidines and imidazo[1,5- a ]pyrimidines proceeding from alkyl 2-benzylidene-3-oxo-3-fluoroalkylpropionates [Electronic resource] / M. V. Pryadeina, Ya. V. Burgart, V. I. Saloutin, P. A. Slepukhin, E. V. Sadchikova, E. N. Ulomskii // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2009. - Vol. 45, № 2. - P242-247 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Methods were developed of the synthesis of alkyl 2-hydroxy-2-fluoroalkyl-4-phenyl-1,2,3,4—tetrahydroimidazo-[1,5-a]pyrimidine-3-carboxylates and alkyl-5-hydroxy-2,7-diphenyl-5-fluoroalkyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-6-carboxylates by regioselective [3+3]-cycloaddition of 5-aminoimidazole or 5-aminopyrazole to alkyl 2-benzylidene-3-oxo-3-fluoroalkylpropionates at the fluoroacylvinyl fragment \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2009, 45 (2), 242.pdf |
S 98 Synthesis of substituted pyrido[1,2-a]pyrimidines from 2-arylmethylidene-3-fluoroalkyl-3-oxopropionates [Electronic resource] / M. V. Pryadeina, Ya. V. Burgart, M. I. Kodess, V. I. Saloutin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2005. - Vol. 54, № 12. - P2841-2845 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CYCLOCONDENSATION -- REGIOISOMERISM -- 2-ARYLMETHYLIDENE Аннотация: Cyclocondensation of 2-arylmethylidene-3-fluoroalkyl-oxopropionates with 2-amino-pyridine occurs at both the polyfluoroacylvinyl and alkoxycarbonylvinyl fragments to give alkyl 4-aryl-2-polyfluoroalkyl-4H-pyrido[1,2-a]pyrimidine-3-carboxylates and 4-aryl-2-hydroxy-3-polyfluoroacyl-4H-pyrido[1,2-a]pyrimidines, respectively. When treated with copper(II) acetate, the pyrido[1,2-a]pyrimidines yield metal complexes \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2005, 54 (12), 2841-2845.pdf |
R 59 Ring-chain isomerism of ethyl 7-polyfluoroalkyl-7-hydroxy-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylates [] / M. V. Pryadeina, Ya. V. Burgart, V. I. Saloutin, O. N. Chupakhin // Mendeleev Communications. - 2008. - Vol. 18, № 5. - С. 276-277. - Bibliogr. : p.277 (10 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Cyclisation of ethyl 2-ethoxymethylidene-3-oxo-3-polyfluoroalkylpropionates with 3-amino-1H-[1,2,4]triazole gives ethyl 7-polyfluoroalkyl-7-hydroxy-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylates that are subject to ring–chain isomerisation in solution, depending on the solvent and the length of the polyfluoroalkyl substituent, to yield ethyl 3-polyfluoroalkyl-3-oxo-2-{([1,2,4]triazol-3-yl)aminomethylidene}propionates via heterocyclic ring opening at the C(7)–N(8) bond \\\\Expert2\\nbo\\Mendeleev Communications\\2008, v.18, p.276.pdf |
F 70 Fluorine-containing heterocycles. XVI. Reactions of tetrafluorobenzoyl isothiocyanate with hydrazines and their derivatives [Electronic resource] / E. V. Nosova, G. N. Lipunova, A. A. Laeva, L. P. Sidorova, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2007. - Vol. 43, № 1. - P68-76 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Fluorinated derivatives of 4H-1,3-benzothiazin-4-one, [1,2,4]triazolo[4,3-a]pyrimidine, [1,2,4]triazolo[3,4-b][1,3]benzazoles, and 1,5-dihydro-1,2,4-triazole-5-thione were synthesized by addition of hydrazines and their derivatives to tetrafluorobenzoyl isothiocyanate, followed by cyclization of intermediate thiosemicarbazides \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2007, 43 (1), 68.pdf |
O-57 One-pot synthesis of 6H-pyrrolo[2,3-e[1,2,4]triazolo[1,5-a]pyrimidines on the basis of delta H-adducts of 6-Nitro[1,2,4]triazolo[1,5-a]pyrimidine with carbonyl compounds [Electronic resource] / E. B. Gorbunov, G. L. Rusinov, R. I. Ishmetova, V. N. Charushin, O. N. Chupakhin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2008. - Vol. 44, № 1. - P128-132 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Aromatic, heteroaromatic, and aliphatic carbonyl compounds reacted with 6-nitro[1,2,4]triazolo[1,5-a]pyrimidine in the presence of a base to give stable ?H-adducts at C7. Reduction of the nitro group in the latter is accompanied by tandem autoaromatization of the azine ring and intramolecular cyclocondensation with formation of the corresponding 6H-pyrrolo[2,3-e][1,2,4]triazolo[1,5-a]pyrimidines \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2008, 44 (1), 128.pdf |
R 30 Reaction of fullerene C60 with 2-azido-4,6-diphenylpyrimidine [Electronic resource] / I. P. Romanova, G. G. Yusupova, D. G. Yakhvarov, O. A. Larionova, N. N. Mochul`skaya, L. P. Sidorova, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2003. - Vol. 52, № 10. - P2171-2174 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The first representative of the pyrimidine-substituted [60]fullereno[1,2-b]aziridines was synthesized by the reaction of fullerene C60 with 2-azido-4,6-diphenylpyrimidine. 2-(Azahomo[60]fullereno)-4,6-diphenylpyrimidine was found to be formed as a by-product. The electrochemical properties of the adducts were studied \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2003, 52 (10), 2171.pdf |
S 98 Synthesis of (7-polyfluoroalkyl)pyrazolo[1,5-a]pyrimidines based on lithium fluorine-containing beta-diketonates [Electronic resource] / V. I. Filyakova, O. A. Kuznetsova, E. N. Ulomskii, T. V. Rybalova, M. I. Kodess, V. L. Rusinov, K. I. Pashkevich // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2002. - Vol. 51, № 2. - P332-336 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reactions of Li enolates of fluorine-containing -diketones with 3-aminopyrazoles afforded (7-polyfluoroalkyl)pyrazolo[1,5-a]pyrimidines. The structure of 3-bromo-2-methyl-5-phenyl-7-trifluoromethylpyrazolo[1,5-a]pyrimidine was established by X-ray diffraction analysis \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2002, 51 (2), 332.pdf |
T 44 Theoretical estimation of the possibility of formation of oxadiazocines in the nucleophilic addition of resorcinol to pyrimidines and synthesis of new azoloannelated benzooxadiazocines [Electronic resource] / E. V. Bartashevich, P. V. Plekhanov, G. L. Rusinov, V. A. Potemkin, A. V. Belik, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1999. - Vol. 48, № 8. - P1553-1557 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A method was proposed for estimating the possibility of cyclization of adducts of resorcinol with pyrimidines to form oxadiazocines based on the conformational criterion and analysis of charges on the C(5) atom of the pyrimidine ring and on the H atom of the hydroxy group of the resulting adducts. A series of new derivatives of 4,5-dihydro-11H-5,11-methanobenzo[g]azolo[1,3,5]oxadiazocines were synthesized. \\\\Expert2\\nbo\\Russian Chemical Bulletin\\1999, 48 (8), 1553.pdf |
N 91 Nucleophilic ring-opening of the azole and azine moieties in 6-nitro-1,2,4-triazolo[1,5-a]pyrimidin-7-ones [Electronic resource] / E. N. Ulomskii, V. V. Voronin, V. L. Rusinov, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2001. - Vol. 50, № 4. - P682-688 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The effects of the nature of the nucleophile and the structure of 6-nitrotriazolo[1,5-a]pyrimidinones on the direction of the ring opening were investigated. The triazole ring is opened under the action of strong bases, such as alkoxides or alkalis, to form 2-cyanoaminopyrimidinones and then 2-aminopyrimidinones. The results of the reactions with N-nucleophiles depend on the accessibility of position 5 of the heterocycle. Thus, sterically hindered secondary amines react with 5-methyltriazolopyrimidinones to give 2-guanidinopyrimidinones and then 2-aminopyrimidinones. In the absence of a substituent at position 5, the azine ring is opened to form 4-alkyl-3-amino-1,2,4-triazoles and 3-amino-2-nitroacrylamides. Under the action of primary amines, only the pyrimidine fragment is cleaved \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2001, 50 (4), 682.pdf |
F 70 Fluorine-containing quinazolines annulated at the pyrimidine ring [Electronic resource] / E. V. Nosova, A. A. Laeva, T. V. Trashakhova, G. N. Lipunova, P. A. Slepukhin, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2009. - Vol. 58, № 6. - P1303-1308 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Fluorine-containing quinazolines annulated at the sides [a] and [c] were synthesized by the reaction of 2- and 4-hydrazino-substituted quinazolines with aldehydes and subsequent oxidative cyclization. Annulation at the side [b] was performed by alkylation of 2-alkylthio-4(3H)-quinazolinones with bromoethanol and ipso-substitution of the alkylthio group \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2009, 58 (6), 1303-1308.pdf |
D 46 Design of fused systems based on sigma(H)-adducts of 6-nitro-1,2,4-triazolo[1,5-a]pyrimidine with pi-excessive heteroaromatic compounds [Electronic resource] / E. B. Gorbunov, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2009. - Vol. 58, № 6. - P1309-1314 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A new method was developed for the construction of tetra- and pentacyclic fused systems based on sigma(H)-adducts of 6-nitro-1,2,4-triazolo[1,5-a]pyrimidine with pi-excessive heteroaromatic compounds. The method involves the reduction of the nitro group accompanied by the aromatization of the dihydropyrimidine ring and followed by the cyclocondensation of the amino derivative with aldehydes \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2009, 58 (6), 1309-1314.pdf |
S 98 Synthesis of methyl 7-aryl-6-(2-thenoyl)-4,7-dihydro-tetrazolo[1,5-a]pyrimidine-5-carboxylates and their reaction with hydrazine hydrate [Electronic resource] / V. L. Gein, V. V. Mishunin, E. P. Tsyplyakova, M. I. Vakhrin, P. A. Slepukhin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2011. - Vol. 47, № 7. - P1077-1082. - Bibliogr. : p. 1082 (5 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Fusion of methyl 4-(2-thienyl)-2,4-dioxobutanoate with 1H-tetrazol-5-amine monohydrate and aromatic aldehyde gave methyl 7-aryl-6-(2-thenoyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-5-carboxylates which reacted with an equimolar amount of hydrazine hydrate at 180-190A degrees C under solvent-free conditions to produce 9-aryl-8-(2-thienyl)-4,9-dihydrotetrazolo[1',5': 1,2]pyrimido[4,5-d]pyridazin-5(6H)-ones \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2011, 47 (7), 1077.pdf |
C 73 Combination of the Suzuki–Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen (HSN) reactions as a versatile route to pyrimidines bearing thiophene fragments / E. V. Verbitskiy, E. M. Cherprakova, P. A. Slepukhin, M. I. Kodess, M. A. Ezhikova, M. G. Pervova, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin // Tetrahedron. - 2012. - Vol.68, №27-28. - С. 5445-5452 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SUZUKI–MIYAURA -- CROSS-COUPLING -- PYRIMIDINES Аннотация: It has been shown that combination of the Suzuki–Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen is a versatile method for the synthesis of 4-(thiophen-2-yl)-, 5-(thiophen-2-yl)-, and 4,5-di(thiophen-2-yl) substituted pyrimidines from the commercially available 5-bromopyrimidine. The HSN (AE)- and HSN (AO)-reactions of 5-bromopyrimidine with thiophene and 2-bromothiophene have been studied by gas–liquid chromatography/mass-spectrometry. The structures of intermediate σH-adducts, as well as thiophene-(thiophenyl)pyrimidine and bithiophene-(thiophenyl)pyrimidine dyads have first been established by X-ray crystallography analysis \\\\Expert2\\nbo\\Tetrahedron\\2012, v. 68, p. 5445.pdf |