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 |
F 71 Fokin, A. S. Fluorine-containing 3-arylhydrazono-2,4-dioxobutanoates in reactions with difunctional nucleophiles [Electronic resource] / A. S. Fokin, Ya. V. Burgart, V. I. Saloutin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2006. - Vol. 42, № 6. - P887-896 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 3-Arylhydrazono-4-polyfluoroalkyl-2,4-dioxobutanoates reacted with hydrazines to give ethyl 4-aryldiazeno-3-polyfluoroalkyl-1H-pyrazole-5-carboxylates, while analogous reactions of ethyl 3-arylhydrazono-4-pentafluorophenyl-2,4-dioxobutanoates resulted in the formation of 4-aryldiazeno-3-pentafluorophenyl-1,2-dihydropyridazine-5,6-diones or 6-aryl-7,8,9,10-tetrafluoro-2-phenyl-2,4a,6,10b-tetradropyridazo[4,3-c]cinnoline-3,4-diones, depending on the conditions. Cyclocondensation of ethyl 3-arylhydrazono-4-polyfluoroalkyl(or pentafluorophenyl)-2,4-dioxobutanoates with ethylenediamine led to 3-[1-arylhydrazono-2-oxo-2-polyfluoroalkyl(or pentafluorophenyl)ethyl]-5,6-dihydropyrazin-2(1H)-ones, and 3-[1-arylhydrazono-2-oxo-2-polyfluoroalkyl(pentafluorophenyl)ethyl]benzoxazin-2-ones were formed in the condensation with o-aminophenol. Pentafluorophenyl-substituted heterocycles were found to undergo intramolecular ring closure to give 3-hetaryl-substituted 1-aryl-5,6,7,8-tetrafluoro-1,4-dihydrocinnolin-4-ones. The reactions of ethyl 3-arylhydrazono-4-pentafluorophenyl-2,4-dioxobutanoates with o-aminobenzenethiol gave 3-[7-(2-aminophenylsulfanyl)-1-aryl-5,6,8-trifluoro-4-oxo-1,4-dihydrocinnolin-3-yl]benzothiazin-2-ones; 8a-hydroxy-11,12,13,14-tetrafluoro-10-(4-methoxyphenyl)-2,3,4,5,6,7,8a,10-octahydropyrazino[1?,2?:4,5][1,4]diazepino[6,7-c]cinnolin-8-one was isolated in the condensation of ethyl 3-(4-methoxyphenylhydrazono)-4-pentafluorophenyl-2,4-dioxobutanoate with N-(2-aminoethyl)ethane-1,2-diamine ?? \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2006, 42 (6), 887.pdf |
R 35 Regioselective cyclocondensation of ethyl 2-ethoxymethylidene-3-oxo-3-polyfluoroalkylpropionates with thiazolylhydrazines [Electronic resource] / M. V. Pryadeina, A. V. Denisova, Ya. V. Burgart, V. I. Saloutin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2008. - Vol. 44, № 12. - P1811-1815 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Ethyl 2-ethoxymethylidene-3-oxo-3-polyfluoroalkylpropionates reacted in a regioselective fashion with thiazolylhydrazines to give the corresponding ethyl 1-thiazolyl-5-fluoroalkyl-1H-pyrazole-4-carboxylates. The product structure was determined on the basis of NMR and X-ray diffraction data \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2008, 44 (12), 1811.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 |
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 |
B 74 Boltacheva, N. S. Fluoroalkyl-Containing Lithium 1,3-Diketonates in Reactions with Amines and Ammonium Salts [Electronic resource] / N. S. Boltacheva, T. I. Filyakova, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2005. - Vol. 41, № 10. - P1452-1457 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Reactions of fluoroalkyl-containing lithium 1,3-diketonates with amines or ammonium salts in glacial acetic acid or methanol at 20°C provide an efficient synthetic route to fluoroalkyl-containing ?-amino-vinyl ketones. Depending on the conditions, reactions of lithium diketonates with 1-aminonaphthalene lead to formation of both ?-aminovinyl ketones and cyclocondensation products, benzo[h]quinolines. The latter can be obtained in one step without isolation of ?-aminovinyl ketones \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2005, 41 (10), 1452.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 |
T 19 Tandem of nucleophilic substitution of hydrogen and cyclocondensation with participation of nitro group in the synthesis of fluorine-containing 3-amino-1,2,4-benzotriazines [Electronic resource] / G. A. Zhumabaeva, S. K. Kotovskaya, N. M. Perova, V. N. Charushin, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2006. - Vol. 55, № 7. - P1243-1247 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Reactions of 3-fluoro-1-nitrobenzenes with guanidine hydrochloride in THF in the presence of ButOK gave isomeric 5-and 7-fluoro-containing 3-amino-1,2,4-benzotriazines \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2006, 55 (7), 1243.pdf |
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 |
F 70 Fluoroalkyl-containing lithium beta-diketonates in the synthesis of 1,2,4-triazolo[1,5-a]pyrimidines [Electronic resource] / O. A. Kuznetsova, V. I. Filyakova, K. I. Pashkevich, E. N. Ulomskii, P. V. Plekhanov, G. L. Rusinov, M. I. Kodess, V. L. Rusinov // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2003. - Vol. 52, № 5. - P1190-1194 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Cyclocondensation of fluorine-containing lithium beta-diketonates with 3-amino-1,2,4-triazoles afforded 7-fluoromethyl-1,2,4-triazolo[1,5-a]pyrimidines \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2003, 52 (5), 1190.pdf |
F 70 Fluorinated azines and benzazines containing oxygen or sulfur atoms [Text] / E. V. Nosova, G. N. Lipunova, V. N. Charushin, O. N. Chupakhin // Journal of Fluorine Chemistry. - 2010. - Vol. 131, № 12. - P1267-1288 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: In the frames of this review article the recently obtained data on synthetic approaches to fluorinated oxa(thia)azines and benzazines, their chemical properties, structure, and biological activity have been analyzed \\\\Expert2\\nbo\\Journal of Fluorine Chemistry\\2010, v. 131, p.1267.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 |
F 98 Fused polycyclic nitrogen-containing heterocycles. 21. Condensation of 4-hydroxy-3,5-diphenyl-2-phenyliminothiazolidine with 5-fluoro-4-morpholino- and 4-(4-methylpiperazino)-1,2-phenylenediamines [Electronic resource] / V. A. Mamedov, N. A. Zhukova, T. N. Beschastnova, A. A. Balandina, A. T. Gubaidullin, S. K. Kotovskaya, Sh. K. Latypov, Ya. A. Levin, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2009. - Vol. 58, № 1. - P203-211 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The condensation of 4-hydroxy-3,5-diphenyl-2-phenyliminothiazolidine with 5-fluoro-4-morpholino- and 5-fluoro-4-(4-methylpiperazino)-1,2-phenylenediamines leads to region-isomeric thiazolo[3,4-a]quinoxalines differing in substituents in positions 7 and 8 of the benzene ring. From the ratio of isomers formed it follows that the mesomeric effect of a fluorine atom in 1,2-phenylenediamines is comparable with the influence of an aminosubstituent \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2009, 58 (1), 203-211.pdf |
S 98 Synthesis of 5-trifluoromethylpyrazol-1-yl-substituted 1,2,4,5-tetrazines [Electronic resource] / S. G. Tolshchina, N. K. Ignatenko, P. A. Slepukhin, R. I. Ishmetova, G. L. Rusinov // Chemistry of Heterocyclic Compounds. - 2010. - Vol. 46, № 6. - P691-698 : рис., табл. Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 5-HYDROXY-5-TRIFLUOROMETHYLPYRAZOLINES -- 1,2,4,5-TETRAZINES -- 1,1,1-TRIFLUORO-2,4-PENTANEDIONE Аннотация: Previously unknown products of the cyclocondensation of 1,1,1-trifluoro-2,4-pentanedione with triaminoguanidine and hydrazine derivatives of 1,2,4,5-tetrazine have been obtained. 5-Hydroxy-5-trifluoromethylpyrazoline substituents formed on the tetrazine ring were dehydrated under the action of trifluoroacetic anhydride. A comparison has been carried out of the reactivity of 5-trifluoromethylpyrazolyl-substituted 1,2,4,5-tetrazines and their unfluorinated analogs in nucleophilic substitution and [4 + 2] cycloaddition reactions \\\\Expert2\\nbo\\Chemistry of Heterocyclic Compounds\\2010, v.46, N 6, p.691-698.pdf |
U 62 Unusual heterocyclization of chalcone podands with 3-amino-1,2,4-triazole / I. G. Ovchinnikova, M. S. Valova, E. G. Matochkina, M. I. Kodess, A. A. Tumashov, P. A. Slepukhin, O. V. Fedorova, G. L. Rusinov, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2011. - Vol.60, №5. - С. 965-974 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): TEMPLATE SYNTHESIS -- CHALCONE PODAND -- CROWN ETHERS Аннотация: A new type of intramolecular cyclization of 1,5-bis[2-(E-3-oxo-3-phenylprop-1-enyl)-phenoxy]-3-oxapentane with 3-aminotriazole promoted by potassium ions was discovered. A cascade mechanism for the formation of crownophane with 4,7-dihydro[1,2,4]triazolo[1,5-a]-pyrimidine fragment was suggested. Effects of oligooxyethylene fragment of the chalcone podand and acid-base catalysis on the selectivity of the cyclocondensation processes and degree of oxidation of triazolopyrimidine fragments were studied. The product structures were confirmed by IR, 1H and 13C NMR spectroscopy and X-ray diffraction study \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2011, 60 (5), 965-974.pdf |
6-Polyfluoroalkylated 2-thiouracils in the synthesis of pyrimido[2,1-b][1,3,5]thiadiazines by the double Mannich reaction [Electronic resource] / O. G. Khudina, A. E. Ivanova, Ya. V. Burgart, V. I. Saloutin, M. A. Kravchenko // Journal of Fluorine Chemistry. - 2013. - Vol.147. - P31-35 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): ALIPHATIC AND AROMATIC AMINES -- ETHYLENEDIAMINE -- FORMALDEHYDE Аннотация: 6-Polyfluoroalkyl-2-thiouracils react with formaldehyde and primary amines in EtOH (MeCN) at 2-mercapto and 3-amino groups to yield pyrimido[2,1-b][1,3,5] thiadiazines via the multicomponent double Mannich reaction. The structure of 3-benzyl-8-nonafluorobutyl-3,4-dihydro-2H,6H-pyrimido[2,1-b][1,3,5] thiadiazin-6-one was studied by the X-ray diffraction analysis. The use of ethylenediamine in these reactions yields 3,3′-ethane-1,2-diyl- bis(pyrimido[2,1-b]thiadiazinone) as a result of the bis-double Mannich cyclocondensation. 8-Polyfluoroalkyl-pyrimido[2,1-b]thiadiazines exhibit weak tuberculostatic activity \\\\Expert2\\NBO\\Journal of Fluorine Chemistry\\2013, v. 147, p.31.pdf |
S 98 Synthesis of New 1,3,4-Thiadiazines Capable of Inhibiting Nonenzymatic Glycosylation of Proteins [Electronic resource] / L. P. Sidorova, T. A. Tseitler, N. M. Perova, V. V. Emel’yanov, E. A. Savateeva, N. E. Maksimova, N. N. Mochul’skaya, V. A. Chereshnev, O. N. Chupakhin // Pharmaceutical Chemistry Journal. - 2015. - Vol. 49, № 8. - С. 501-505. - Bibliogr. : p. 505 (12 ref.) Рубрики: ЗДРАВООХРАНЕНИЕ. МЕДИЦИНСКИЕ НАУКИ ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 1,3,4-THIADIAZINE -- CYCLOCONDENSATION -- NONENZYMATIC GLYCOSYLATION OF PROTEINS -- THIOSEMICARBAZIDES Аннотация: A series of new 1,3,4-thiadiazines with cycloalkylamino (cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino) groups were synthesized via cyclocondensation of α-haloacetophenones with thiosemicarbazides containing 4-cycloalkyl groups. Five of the synthesized compounds showed the capability to inhibit nonenzymatic glycosylation of proteins in vitro in a model system. The obtained test results allowed compounds containing cyclopropylamino residues (LT-1a and LT-1d) to be recommended for further in vivo testing \\\\expert2\\nbo\\Pharmaceutical Chemistry Journal\\2015, 49 (8), 501-505.pdf |
S 98 Synthesis and antitumour activity of 4-aminoquinazoline derivatives [Electronic resource] / G. N. Lipunova, E. V. Nosova, V. N. Charushin, O. N. Chupakhin // Russian Chemical Reviews. - 2016. - Vol. 85, № 7. - С. 759-793 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): GROWTH-FACTOR RECEPTOR -- POTENT EGFR INHIBITORS -- TYROSINE KINASE INHIBITORS Аннотация: Scieces of data on the synthesis and antitumour activity of 4-aminoquinazolines are summarized and analyzed. Key methods for the synthesis of these compounds are considered, primarily cyclocondensation of carboxylic acid derivatives, as well as the oxidation of quinazolines and the cyclization of disubstituted thioureas. Improvements of synthetic schemes for erlotinib, gefitinib and lapatinib, which are the best-known pharmaceuticals based on compounds of the title class, are also considered. Synthetic strategies and biological activities for new 4-aminoquinazoline derivatives that are EGFR-tyrosine kinase inhibitors, multiactive compounds, and labelled compounds for use as positron emission tomography (PET) imaging agents are discussed. |
Expanding 1,2,4-triketone toolbox for use as fluorinated building blocks in the synthesis of pyrazoles, pyridazinones and β-diketohydrazones / Y. O. Edilova, Y. V. Burgart, V. I. Saloutin [et al.] // Journal of fluorine chemistry. - 2022. - Vol. 253. - Ст. 109932 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Fluorinated lithium β-diketonates bearing a methyl acetal group behave in the condensation reactions with hydrazines as trielectrophilic building blocks for the preparation of pyrazoles, pyridazinones and β-diketohydrazones. For the first time, solvent-induced regioisomeric and heterocyclic ring size-controlled formation was observed for 1,2,4-triketone analogues. Fluoroalkylated acetyl NH-pyrazoles or substituted 5-RF-pyrazoles were obtained from the acid-catalyzed cyclocondensation of lithium β-diketonates with (aryl)hydrazines in ethanol. In methanol solvent acetyl-containing 3-CF3-pyrazoles were isolated because of inverse nucleophilic attack of arylhydrazines. The use of aprotic acetonitrile in the condensation resulted in regioselective trifluorinated pyridazinones and fluorinated β-diketohydrazones formation via initial acetal fragment interaction with N,N-dinucleophile. |