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 |
S 98 Synthesis of 7-alkyl(aryl)-6-alkoxycarbonyl-5-fluoroalkyl-1,2,4-tri(tetr)azolo[1,5-a]pyrimidines [Electronic resource] / M. V. Pryadeina, Ya. V. Burgart, V. I. Saloutin, M. I. Kodess, E. N. Ulomskii, V. L. Rusinov // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2004. - Vol. 40, № 6. - P902-907. - Библиогр. : с. 906 (14 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Fluorinated 3-oxo esters react with aldehydes and 3-amino-1,2,4-triazoles and 5-aminotetrazoles to give, respectively, 7-alkyl(aryl)-6-alkoxycarbonyl-5-fluoroalkyl-1,2,4-triazolo[1,5-a]pyrimidines and -tetra-zolo[1,5-a]pyrimidines. The same heterocyclic products can be obtained by reaction of 2-benzylidene-2-fluoroacyl esters with the corresponding aminoazoles \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2004, 40 (6), 902-907.pdf |
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 |
N 52 New reactions of fluorinated 2,4-dioxoesters with aromatic aldehydes [Electronic resource] / M. V. Pryadeina, O. G. Khudina, Ya. V. Burgart, V. I. Saloutin, O. N. Chupakhin // Mendeleev Communications. - 2006. - Vol. 16, № 3. - P188-189 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 4-Polyfluoroalkyl 2,4-dioxobutanoates react with aromatic aldehydes to give 4-aryl-2,6-dihydroxy-2,6-di (fluoroalkyl)-3,5-diethoxalyltetrahydropyrans 3a,b, whereas the reaction of 4-pentafluorobenzoyl 2,4-dioxobutanoate with benzaldehyde gives 5,6,7,8-tetrafluoro-1-phenyl-1H-furo[3,4-b]chromene-3,9-dione 4. \\\\Expert2\\nbo\\Mendeleev Communications\\2006, v.16, p.188.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 |
C 73 Condensation of 2-polyfluoroacycloalkanones with aldehydes and dimethylformamide-dimethylacetal [Text] / D. V. Sevenard, O. G. Khomutov, M. I. Kodess, K. I. Pashkevich, I. Loop, E. Lork, G. -V. Roeschenthaler // Australian Journal of Chemistry. - 2001. - Vol. 54, № 3. - P157-163 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Polyfluorinated 1,3-diketones containing carbocycles react with aldehydes under Lewis-acid catalysis and also with dimethylformamide-dimetylacetal without catalysis, yielding exclusively (E)-configured condensation products involving the methylene group of the carbocycle. Novel trifluoromethylated chromenes are prepared from 2-trifluoroacetylcycloalkanones and salicylaldehyde. The structures of two new compounds, 2-(E)-benzylidene-6-trifluoroacetylcyclohexanone and 4-trifluoroacetyl-2,3-dihydro-1H-xantene, are confirmed by X-ray structure analysis. |
A 10 A versatile strategy for the synthesis of functionalized 2,2 '-bi- and 2,2 ': 6 ',2 '-terpyridines via their 1,2,4-triazine analogues [Text] / V. N. Kozhevnikov, D. N. Kozhevnikov, T. V. Nikitina, V. L. Rusinov, O. N. Chupakhin, M. Zabel, B. Konig // Journal of Organic Chemistry. - 2003. - Vol. 68, № 7. - P2882-2888 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ALDEHYDES -- OXIDATION -- SUBSTITUTION REACTIONS Аннотация: A general synthetic route for the synthesis of functionalized bi- and terpyridines is reported. Functionalized 1,2,4-triazene 4-oxides 7 and 8 - obtained from the reaction of hydrazones 1 with pyridine aldehydes and followed by oxidation - are functionalized by introduction of a cyano group via nucleophilic aromatic substitution. The thus-obtained 5-cyano-1,2,4-triazines 9 and 10 undergo facile inverse-electron-demand Diels-Alder reactions with enamines and alkenes to yield functionalized bi- and terpyridines, respectively. The substituent at position 6 of the 1,2,4-triazene 4-oxides must be aromatic or heteroaromatic in order to allow their facile synthesis, but other substituents and reagents may vary. Each step of the synthetic route allows diversification, which makes the approach particularly useful for the facile synthesis of a large variety of functionalized bi- and terpyridines. \\\\Expert2\\nbo\\Journal of Organic Chemistry\\2003, v.68, N 7, p.2882. Chupakhin.pdf |
R 30 Reactions of fluorine-containing 3-oxo esters with aldehydes [Text] / M. V. Pryadeina, O. G. Kuzueva, Ya. V. Burgart, V. I. Saloutin, K. A. Lyssenko, M. Yu. Antipin // Journal of Fluorine Chemistry. - 2002. - Vol. 17, № 1. - P1-7 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Fluoroalkylcontaining 3-oxo esters react with aldehydes to form 2-benzylidene-3-fluoroacyl-esters or 4-aryl(alkyl)-3,5-dialkoxycarbonyl-2,6-dihydroxy-2,6-di(fluoroalkyl)tetrahydropyranes depending on the conditions. Ethyl pentafluorobenzoylacetoacetate with benzaldehyde affords 3,5-diethoxy-carbonyl-4-phenyl-2-pentafluorophenyl-7,8,9,10-tetrafluoro-4,5-dihydrobenzo[b]oxacin-6-one |
S 98 Synthesis of 5-and 7-fluoroquinazolin-4(1H)-ones [Electronic resource] / A. A. Layeva, E. V. Nosova, G. N. Lipunova, T. V. Trashakhova, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2007. - Vol. 56, № 9. - P1821-1827 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 5-Fluoroquinazoline-2,4-diones and their 2-thio analogs were obtained from 6-fluoroanthranilic acid. Two convenient routes to 5-fluoroquinazolin-4-ones involved cyclocondensation of 6-fluoroanthranilamide with acid chlorides (anhydrides) or with aromatic (heterocyclic) aldehydes. A method for the synthesis of 7-fluoroquinazolin-4-one from 2,4-difluorobenzoic acid was proposed \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2007, 56 (9), 1821.pdf |
S 98 Synthesis, Structure, and Keto-Enol Tautomerism of 3-R1-5,5-R2,R2-6-R3-2,3,5,6-Tetrahydropyran-2,4-diones [Electronic resource] / V. V. Shchepin, M. I. Kodess, Yu. Kh. Sazhneva, N. Yu. Russkikh // Russian Journal of General Chemistry. - 2005. - Vol. 75, № 10. - P1622-1627 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Ethyl esters of 2,4-dibromo-2-R1-4-R2-3-oxopentanoic and -hexanoic acids react with zinc and aliphatic or aromatic aldehydes under the conditions of the Reformatskii reaction to give 3-R1-5,5-R2, R2-6-R3-2,3,5,6-tetrahydropyran-2,4-diones, which are obtained in three forms: keto, enol with enolization of the keto group, and enol with enolization of the ester group. The keto form is isolated by crystallization from a mixture of CCl4 and petroleum ether; the first enol form, from MeOH, EtOH, and polar aprotic solvents; and the second enol form, from CHCl3. The second enol form is oxidized in DMSO to form a keto compound containing a hydroxy group at the 3-position of the heteroring \\\\Expert2\\nbo\\Russian Journal of General Chemistry\\2005, V. 75, N 10, p.1622.pdf |
M 20 Makosza, M. Vicarious nucleophilic substitution of hydrogen in aldehydes and Knoevenagel reaction of iminium salts with ?-halocarbanions [Electronic resource] / M. Makosza, D. N. Kozhevnikov // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2001. - Vol. 50, № 11. - P2236-2238 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Iminium salts derived from aromatic aldehydes react with -chlorocarbanions via two different pathways: reaction with secondary carbanion of halomethyl sulfones proceeds as the Knoevenagel condensation, while tertiary -chlorocarbanions gave products of vicarious nucleophilic substitution of hydrogen in parent aldehydes \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2001, 50 (11), 2236.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 |
E 27 Effective fluoroalkylation of aldehydes by delta-perfluoroalkyl-iron compounds [Text] / V. G. Ratner, V. B. Korolev, D. L. Chizhov, K. I. Pashkevich // Journal of Fluorine Chemistry. - 1992. - Vol. 58, № 2-3. - P355 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Organoiron compounds with ?-perfluoroalkyl-iron bonds are well-known and common compounds convenient to prepare and handle. However, their application in organic synthesis was restricted to the introduction of fluoroalkyl group only into electron rich organic molecules such as arenes and thiols |
A 89 Asymmetric azomethine ligands based on 2-[(2-aminophenyl)aminomethylidene]-3-oxo-3-polyfluoroalkylpropionates and aldehydes [Electronic resource] / Yu. S. Kudyakova, M. V. Goryaeva, Ya. V. Burgart, V. I. Saloutin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2010. - Vol. 59, № 9. - P1753-1760 : рис., табл. - Bibliogr. : p. 1759-1760 (12 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): AZOMETHINES -- ALDEHYDES -- LIGANDS -- NICKEL(II) COMPLEXES -- COPPER(II) COMPLEXES -- ORGANOFLUORINE COMPOUNDS -- X-RAY DIFFRACTION STUDY Аннотация: The condensation of ethyl 2-[(2-aminophenyl)aminomethylidene]-3-oxo-3-polyfluoroalkyl-propionates with aldehydes (salicylaldehyde, furfural, and benzaldehyde) affords the corresponding azomethine derivatives exhibiting the complexing ability toward copper and nickel ions. \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2010, 59 (9), 1753-1760.pdf |
S 98 Synthesis of 2,6-bis(fluoroalkyl)-2,6-dihydroxytetrahydro-2H-pyran-3,5-dicarboxylates from aldehydes and fluorinated beta-oxo esters in the presence of ionic liquid-K2CO3 as catalytic system [Electronic resource] / S. G. Zlotin, G. V. Kryshtal’, G. M. Zhdankina, A. V. Ignatenko, Ya. V. Burgart, V. I. Saloutin, O. N. Chupakhin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2010. - Vol. 46, № 4. - P468-473 : рис., табл. - Bibliogr. : p. 472-473 (35 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): DICARBOXYLATES -- ALDEHYDES -- ESTERS -- CATALYTIC SYSTEM Аннотация: An efficient procedure has been developed for the synthesis of 4-substituted 2,6-bis(fluoroalkyl)-2,6-dihydroxytetrahydro-2H-pyran-3,5-dicarboxylates by reactions of aldehydes with fluorine-containing ?-oxo esters in heterogeneous catalytic system 1-butyl-3-methylimidazolium tetrafluoroborate [bmim][BF4]-K2CO3 activated by ultrasound. The system retains its catalytic activity for three reaction cycles. \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2010, 46 (4), 468-473.pdf |
S 98 Synthesis and photophysical properties of 2-styrylquinazolin-4-ones [Electronic resource] / T. V. Trashakhova, E. V. Nosova, M. S. Valova, P. A. Slepukhin, G. N. Lipunova, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2011. - Vol. 47, № 5. - P753-761. - Bibliogr. : p. 761 (16 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: trans-2-Styryl-substituted 3H-, 3-phenyl-, and 3-naphthylquinazolin-4-ones and their 6,7-difluoro derivatives were synthesized by condensation of appropriate 2-methylquinazolin-4-ones with aromatic aldehydes or by the transformation of the heterocycle of 2-methyl-3,1-benzoxazin-4-one under the action of benzylidenephenylamines \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2011, 47 (5), 753-761.pdf |
1,3-Dipolar cycloadditions of nonstabilised azomethine ylides at 3-substituted coumarins: synthesis of 1-benzopyrano[3,4-c]pyrrolidines / V. S. Moshkin, V. Ya. Sosnovskikh, P. A. Slepukhin, Gerd-Volker Röschenthalerc // Mendeleev Communications. - 2012. - Vol.22, №1. - С. 29-31 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): COUMARINS -- AZOMETHINE YLIDES -- PYRROLIDINES Аннотация: Reaction of 3-substituted coumarins with N-alkyl-α-amino acids and aldehydes proceeds regio- and stereoselectively to give 1-benzopyrano[3,4-c]pyrrolidines as a result of 1,3-dipolar cycloaddition of the intermediate azomethine ylides at the Δ3-bond of the coumarins \\\\Expert2\\nbo\\Mendeleev Communications\\2012, v.22, p. 29.pdf |
S 98 Synthesis of N-substituted 7-aryl-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxamides / V. L. Gein, T. M. Zamaraeva, N. V. Nosova, M. I. Vakhrin, P. A. Slepukhin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2012. - Vol.48, №3. - С. 419-422 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHESIS -- 6-CARBOXAMIDES -- PYRIMIDINE Аннотация: Three-component reaction of N-methyl- or N,N-diethyl-3-oxobutanamide with aromatic aldehydes and tetrazol-5-amine monohydrate gave the corresponding N-substituted 7-aryl-5-methyl-4,7-dihydrotetrazolo-[1,5-a]pyrimidine-6-carboxamides \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2012, 48 (3), 419-422.pdf |
F 70 Fluorine containing quinoline and quinoxaline styryl derivatives: [Electronic resource] / E. V. Nosova, T. V. Trashakhova, V. S. Ustyugov, N. N. Mochul`skaya, M. S. Valova, G. N. Lipunova, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2013. - Vol.60, №5. - С. 942-947. - Bibliogr. : p. 946-947 (25 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): STYRYLBENZAZINES -- PHOTOLUMINESCENCE -- 6,7-DIFLUOROQUINALDINE Аннотация: (E)-2-Styryl-substituted 6,7-difluoroquinolines and quinoxalines were synthesized by the condensation of the corresponding 2 methylbenzazines with aromatic aldehydes. Photolumines cence of the synthesized 6,7 difluoro 2 styrylbenzazines was studied \\\\expert2\\NBO\\Russian Chemical Bulletin\\2011, 60 (5), 942-947.pdf |