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, analgesic and antipyretic activity of 2-(antipyrin-4-yl)hydrazones of 1,2,3-triketones and their derivatives [Electronic resource] / E. V. Shchegol'kov, O. G. Khudina, L. V. Anikina, Ya. V. Burgart, V. I. Saloutin // Pharmaceutical Chemistry Journal. - 2006. - Vol. 40, № 7. - P373-376. - Библиогр. : с. 376 (10 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 1,2,3-Triketone 2-(antipyrin-4-yl)hydrazones were synthesized via the azo-coupling reactions of 1,3-diketones with 2-(antipyrin-4-yl)diazonium chloride. The fluoroalkyl-containing hetarylhydrazone enters into cyclocondensation with hydrazines at the 1,3-dicarbonyl fragment to yield 3-tetrafluoroethyl derivatives of pyrazole. It was found that 1,2,3-triketone 2-(antipyrin-4-yl)hydrazones and N-(2-hydroxyethyl)-substituted pyrazole exhibit analgesic activity comparable with that of their structural analog analgin (metamizole sodium), but do not possess antipyretic properties. In contrast, N-phenyl-substituted pyrazole did not exhibit analgesic properties but produced a certain antipyretic effect four hours after pyrogenic administration. Fluoroalkyl-containing compounds are less toxic substances than nonfluorinated 2-(antipyrin-4-yl)hydrazone and analgin. \\\\Expert2\\nbo\\Pharmaceutical Chemistry Journal\\2006, 40 (7), 373-376.pdf |
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 |
F 94 From oxides of internal perfluoroolefins to fluorocontaining camphor thiazolinylhydrazones [Text] / L. V. Saloutina, A. Ya. Zapevalov, M. I. Kodess, K. A. Lyssenko, M. Yu. Antipin, V. I. Saloutin, O. N. Chupakhin // Journal of Fluorine Chemistry. - 2003. - Vol. 120, № 1. - P41-47 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reaction of oxides of internal trans- and cis-perfluoroolefins with (1S, 4S)- or racemic camphor thiosemicarbazone leads to the formation of trans- and cis-isomers of (1S, 4S)- or racemic camphor 5?-fluoro-4?-hydroxy-4?,5?-di(perfluoroalkyl)-1?,3?-thiazolinyl-2?-hydrazones, respectively. Unsymmetrical dodecafluoro-2,3-epoxyhexane yields a mixture of regioisomeric hydrazones. The molecular structure of the trans-isomer of (1S, 4S)-camphor 5?-fluoro-4?-hydroxy-4?,5?-bis(trifluoromethyl)-1?,3?-thiazolinyl-2?-hydrazone has been established by X-ray crystallography. The quite rare example of cocrystallization of two diastereomers of the latter in homochiral crystal (sp. group P21) has been revealed???? |
S 98 Synthesis, structure, and complexing ability of fluoroalkyl-containing 2,2-(biphenyl-4,4-diyldihydrazono)bis(1,3-dicarbonyl) compounds [Electronic resource] / I. V. Shchur, O. G. Khudina, Ya. V. Burgart, V. I. Saloutin, M. A. Grishina, V. A. Potemkin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2007. - Vol. 43, № 12. - P1781-1787 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: New fluoroalkyl-containing 2,2?-(biphenyl-4,4?-diyldihydrazono)bis(1,3-diketones) and 2,2?-(biphenyl-4,4?-diyldihydrazono)bis(3-oxopropionates) were synthesized by azo coupling of the corresponding 1,3-dicarbonyl compounds with biphenyl-4,4?-bis(diazonium) dichloride. Complexing ability of the obtained bis-hydrazones was studied, and new coordination compounds of the general formula M2L2 [where M = Ni(II), Cu(II); L = fluoroalkyl-containing 2,2?-(biphenyl-4,4?-diyldihydrazono)bis(1,3-diketone)] were obtained \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2007, 43 (12), 1781.pdf |
S 98 Synthesis of fluoroalkyl-containing 1,2,3-triketone 2-hetarylhydrazones and their reactions with hydrazines [Electronic resource] / E. V. Shchegol'kov, Ya. V. Burgart, O. G. Khudina, V. I. Saloutin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2004. - Vol. 53, № 11. - P2584-2590 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Fluoroalkyl-containing 1,2,3-triketone 2-(2,3-dimethyl-5-oxo-1-phenyl-1,2-dihydropyrazol-4-yl)-, 2-(4-ethoxycarbonylpyrazol-3-yl)-, and 2-(1,2,4-triazol-3-yl)hydrazones were synthesized by the azo coupling reactions of fluorinated 1,3-diketones with the corresponding hetaryldiazonium chlorides. The hetarylhydrazones thus synthesized were subjected to cyclocondensation with hydrazines at the 1,3-dicarbonyl fragment to give 3-fluoroalkyl-4-hetarylazopyrazoles \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2004, 53 (11), 2584-2590.pdf |
R 30 Reaction of internal fluoroolefin oxides with camphor thiosemicarbazone [Electronic resource] / 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). - 2001. - Vol. 37, № 11. - P1522-1527. - Bibliogr. : p. 1527 (9 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): OXIDES -- FLUOROOLEFIN OXIDES -- CAMPHOR THIOSEMICARBAZONE -- DERIVATIVES -- EPOXY DERIVATIVES Аннотация: Epoxy derivatives of internal fluoroolefins (both cis and trans isomers) react in a stereospecific manner with (1S)-or rac-camphor thiosemicarbazone in a polar aprotic medium to give the corresponding 5-fluoro-4-hydroxy-4,5-bis(polyfluoroalkyl)thiazol-2-ylhydrazones. From unsymmetrical 2,3-epoxydodeca-fluorohexane a mixture of regioisomeric hydrazones is formed. According to the 1H and 19F NMR data, the resulting trans-hydrazones in (CD3)2SO and CDCl3 exist as mixtures of diastereoisomers occurring in a dynamic equilibrium. \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2001, 37 (11), 1522.pdf |
P 30 Pashkevich, K. I. Reactions of regioisomeric fluoroalkyl-containing beta-aminovinyl ketones with hydrazines [Electronic resource] / K. I. Pashkevich, V. I. Filyakova, O. A. Kuznetsova // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1996. - Vol. 45, № 12. - P2868-2870 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Fluoroalkyl beta-alkyl--beta-aminovinyl ketones react with hydrazine hydrate to give the respective razoles and with phenylhydrazine they form a mixture of pyrazoles and 5 hydroxy-2-pyrazolines. Alkyl(aryl) -fluoroalkyl--aminovinylketones do not react with the hydrazines mentioned above. With 2,4-dinitrophenylhydrazine, both types of fluoroalkyl-containing -aminovinyl ketones give only hydrazones of the corresponding methyl alkyl(aryl) ketones \\\\Expert2\\nbo\\Russian Chemical Bulletin\\1996, 45 (12), 2868.pdf |
S 73 Sosnovskikh, V. Ya. Reaction of 3,3-dialkyl-6-trifluoromethyl-2,3-dihydro-4-pyrones with hydrazine hydrate [Electronic resource] / V. Ya. Sosnovskikh, M. Yu. Mel'nikov, M. I. Kodess // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1998. - Vol. 47, № 7. - P1365-1368 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 3,3-Dialkyl-2,3-dihydro-6-trifluoromethyl-4-pyrones react with hydrazine hydrate to give 2-hydrazino-2-trifluoromethyl-4-tetrahydropyrone hydrazones. When heated, the latter are transformed into 3(5)-(2-hydroxyethyl)-5(3)-trifluoromethylpyrazoles, while their treatment with HCl in ether leads to 3,3-dialkyl-2,3-dihydro-6-trifluoromethyl-4-pyrone azines \\\\Expert2\\nbo\\Russian Chemical Bulletin\\1998, 47 (7), 1365.pdf |
U 52 Unexpected products in the reactions of s-tetrazine hydrazones with enamines [Text] / G. L. Rusinov, R. I. Ishmetova, I. N. Ganebnuikh, O. N. Chupakhin, G. G. Aleksandrov, I. A. Litvinov, D. B. Krivolapov // Heterocyclic communications. - 2003. - Vol. 9, № 1. - P39-44 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: For the first time in the reactions of some 1,2,4,5-tetrazine hydrazones with enamines in addition to the expected products of Carbony-Lindsey reaction the unusual addition and cyclization products at cyclic and exocyclic nitrogen atom of tetrazine ring have been isolated. |
S 78 Spiro[4H-chromene-4,5-isoxazolines] and related compounds: Synthesis and reactivities [Electronic resource] / V. Ya. Sosnovskikh, A. Yu. Sizov, B. I. Usachev, M. I. Kodess, V. A. Anufriev // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2006. - Vol. 55, № 3. - P535-542 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Reactions of chromones with methyl ketoximes in the presence of lithium diisopropylamide follow the nucleophilic 1,2-addition mechanism to give spiro[4H-chromene-4,5?-isoxazolines] in good yields. The isoxazoline ring in spiro[4H-chromene-4,5?-isoxazolines] undergoes opening under the action of conc. H2SO4, yielding ?,?-unsaturated oximes. Their nitrosation and bromination lead to the corresponding spiroisoxazolines, while the Beckmann rearrangement, to ?,?-unsaturated amides. The latter are also formed directly from spiro[4H-chromene-4,5?-isoxazolines] under the action of PCl5. N-Substituted acetophenone hydrazones in the presence of lithium diisopropylamide react at the C(4) atom of 2-trifluoromethylchromone, while acetophenone anil under the same conditions, at the C(2) atom \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2006, 55 (3), 535.pdf |
S 98 Synthesis of fused quinoxalines [Electronic resource] / M. G. Ponizovskii, A. M. Boguslavskii, M. I. Kodess, V. N. Charushin, O. N. Chupakhin // Mendeleev Communications. - 2002. - Vol. 12, № 2. - P68-70 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The intramolecular cyclization of NH and N-alkyl quaternary salts of 2-quinoxaline-2-carboxaldehyde hydrazones affords pyrazolo- [3,4-b]quinoxalines in good yields \\\\expert2\\nbo\\Mendeleev Communications\\2002, v.12, N 2. p.68.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 |
S 98 Synthesis, structure, and photochemical properties of hetarylaldehydes benzimidazolyl-2-hydrazones [Electronic resource] / I. G. Pervova, S. A. Melkozerov, P. A. Slepukhin, G. N. Lipunova, V. A. Barachevskii, I. N. Lipunov // Russian Journal of General Chemistry. - 2010. - Vol. 80, № 5. - P987-993 : рис., табл. Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: New benzimidazolyl-2-hydrazones of 2-furaldehyde, thiophene-2-carbaldehyde and pyridine-2-carbaldehyde were synthesized and their structure was studied by H-1 NMR and X-ray analysis. Photochemical properties of these compounds and of benzothiazolyl-2-hydrazones of 2-furaldehyde, thiophene-2-carbaldehyde and pyridine-2-carbaldehyde in solutions were investigated. The process of phototransformation is determined by the nature of the aldehyde fragment of hydrazones \\\\Expert2\\nbo\\Russian Journal of General Chemistry\\2010, V. 80, N 5, p.987.pdf |
R 30 Reactions of 2-arylhydrazonoacetamidoximes with orthoesters [Electronic resource] / N. P. Belskaia, A. V. Koksharov, S. G. Lesogorova, P. A. Slepukhin, V. A. Bakulev // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2011. - Vol.60, №5. - С. 889-895. - Bibliogr. : p. 895 (11 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): HYDRAZONES -- AMIDOXIMES -- ORTHOESTERS Аннотация: The reactions of 2 arylhydrazono 2 carbamoylacetamidoximes with orthoesters afford either 3 arylhydrazono 1,2,4 oxadiazoles or 1,2,3 triazoles, depending on the reactant structure. \\\\expert2\\NBO\\Russian Chemical Bulletin\\2011, 60 (5), 869-875.pdf |
2-Hydroxybenzaldehyde (2-phenylquinazolin-4-yl)hydrazones [Electronic resource] / T. V. Trashakhova, E. V. Nosova, P. A. Slepukhin, M. S. Valova, G. N. Lipunova, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2011. - Vol.60, №11. - С. 2347-2353. - Bibliogr. : p. 2353 (23 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SALICYLIDENEHYDRAZINE -- ZINC(II) COMPLEXES -- PHOTOLUMINESCENT Аннотация: N-(2-Phenylquinazolin-4-yl)-N´ salicylidenehydrazines and their ZnII complexes were obtained. The structures and luminescent properties of these new quinazoline derivatives were examined \\\\expert2\\NBO\\Russian Chemical Bulletin\\2011, 60 (11), 2347-2353.pdf |
S 98 Synthesis and photoluminescence properties of zinc(II) complexes with salicylaldehyde hetarylhydrazones [Electronic resource] / S. A. Melkozerov, I. G. Pervova, G. N. Lipunova, V. A. Barachevskii, I. N. Lipunov, E. A. Dvoskin // Russian Journal of General Chemistry. - 2013. - Vol.83, №4. - С. 646-651. - Bibliogr. : p. 651 (13 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ZINC(II) COMPLEXES -- SALICYLALDEHYDE BENZAZOLYL -- PYRIMIDINYLHYDRAZONES Аннотация: New zinc complexes of the salicylaldehyde benzazolyl- and pyrimidinylhydrazones were synthesized. Study of photophysical properties of the hydrazones and their complexes in solution showed that their structure and the luminescence intensities depend on the nature of the heterocyclic fragment included to the molecule \\\\expert2\\nbo\\Russian Journal of General Chemistry\\2013, V. 83, N 4, p. 646–651.pdf |
F 62 Five-membered 2,3-dioxo heterocycles: CI. Reaction of 3-aroylpyrrolo[2,1-c] [1,4]benzoxazine-1,2,4-triones with arylhydrazines. Crystal and molecular structure of substituted 2-hydrazonopyrrolo[2,1-c][1,4]benzoxazine [Electronic resource] / I. V. Mashevskaya, N. V. Suchkova, L. V. Kusina, P. A. Slepukhin, A. N. Maslivets // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2014. - Vol.50, №3. - С. 425-428. - Bibliogr. : p. 428 (6 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): NUCLEOPHILIC ATTACK -- HETEROCYCLES -- 1,2,4-TRIONES Аннотация: A new direction of nucleophilic attack was revealed in the reactions of 3-aroylpyrrolo[2,1-c][1,4]-benzoxazine-1,2,4-triones with o-tolylhydrazine and 2-hydrazinylbenzoic acid hydrochloride, which afforded the corresponding hydrazones at the C2=O carbonyl group, substituted 2-(2-o-tolylhydrazono)pyrrolo[2,1-c]-[1,4]benzoxazine-1,4(2H)-diones and pyrrolo[2,1-c][1,4]benzoxazin-2(4H)-ylidenehydrazinylbenzoic acids. The structure of (Z)-2-{2-[3-benzoyl-1,4-dioxo-1H-pyrrolo[2,1-c][1,4]benzoxazin- 2(4H)-ylidene]hydrazinyl}-benzoic acid was determined by X-ray analysis \\\\expert2\\nbo\\Russian Journal of Organic Chemistry\\2014, 50, (3), 425-428.pdf |
Synthesis of 5-(4-bromophenyl)- and 5-(5-bromothiophen-2-yl)-substituted 3-aryl[1,2,4]triazolo[4,3-c]quinazolines / E. V. Nosova, A. E. Kopotilova, M. A. Ivan’kina [et al.] // Russian chemical bulletin. - 2022. - Vol. 71, № 7. - P1483-1487 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A series of [1,2,4]triazolo[4,3-c]quinazolines, bearing 3-positioned p-bromophenyl or 5-bromothiophen-2-yl fragment, was synthesized by oxidative cyclization of the corresponding hydrazones with bromine in glacial acetic acid at room temperature. The obtained tricyclic derivatives are valuable intermediates for biologically active compounds and fluorophores. |