C 52 Chizhov, D. L. Reactions of fluoroalkyl-containing bis-beta-diketones with hydrazine and hydroxylamine [Electronic resource] / D. L. Chizhov, V. G. Ratner, K. I. Pashkevich // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1999. - Vol. 48, N 4. - P758-760 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Polyfluoroalkyl-containing bis(5-hydroxy-Delta(2)-isoxazolines), and bisisoxazoles were synthezed for the first time by reactions of polyfluoroalkyl-containing bis-beta-diketones with hydrazine, phenylhydrazine, and hydroxylamine, respectively \\\\Expert2\\nbo\\Russian Chemical Bulletin\\1999, 48 (4), 758-760.pdf |
S 51 Sevenard, D. V. Interaction of 2-polyfluoroalkyl Cyclalkanones with Hydroxylamine and Hydrazines [Text] : доклад, тезисы доклада / D. V. Sevenard, O. G. Khomutov, K. I. Pashkevich // International Memorial I.Postovsky Conference on Organic Chemisty, Ekaterinburg, March 17-20, 1998 : program and abstracts. - Ekaterinburg, 1998. - P119 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
K 66 Kodess, M. I. Reactions of 3-(polyfluoroacyl)chromones with hydroxylamine : synthesis of novel R - containing isoxazole and chromone derivatives [Electronic resource] / M. I. Kodess, V. Ya. Sosnovskikh, V. S. Moshkin // Tetrahedron. - 2008. - Vol. 64, № 34. - P7877-7889 : рис. - Библиогр. : с. 7888-7889 (32 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Reaction of 3-(polyfluoroacyl)chromones with hydroxylamine free base proceeds via nucleophilic 1,4-addition followed by opening of the pyrone ring and subsequent cyclization to 4-(polyfluoroalkyl)-4H-chromeno[3,4-d]isoxazol-4-ols in good yields. On treatment with trifluoroacetic acid, the isoxazole ring of this annulated heterocyclic system opens to give 3-cyano-2-(polyfluoroalkyl)chromones, which were successfully hydrolyzed with concentrated H2SO4 to afford 3-carbamoyl-2-(polyfluoroalkyl)chromones. On the other hand, oximation of 3-(polyfluoroacyl)chromones with hydroxylamine hydrochloride occurs either at the carbonyl carbon atom connected to the RF group or at the C-2 atom to give 3-RFC(NOH)-chromones and 5-RF-4-salicyloylisoxazole oximes, respectively. The former were easily converted to 3-RF-4-salicyloylisoxazoles by simple heating in dimethyl sulfoxide.?? \\\\Expert2\\nbo\\Tetrahedron\\2008, v. 64, N34, p. 7877.pdf |
T 44 The amidine rearrangement in 5-amino-6-aryl-1,2,4-triazine-4-oxides initiated by hydroxylamine [Text] / O. N. Chupakhin, V. N. Kozhevnikov, A. M. Prokhorov, D. N. Kozhevnikov, V. L. Rusinov // Tetrahedron Letters. - 2000. - Vol. 41, № 38. - P7379-7382 Рубрики: ХИМИЧЕСКИЕ НАУКИ |
S 98 Synthesis of fluorinated 2(3)-arylhydrazones of 1,2,3-tri(1,2,3,4-tetra)carbonyl compounds and their heterocyclization reactions [] / Ya. V. Burgart, A. S. Fokin, O. G. Kuzueva, O. N. Chupakhin, V. I. Saloutin // Journal of Fluorine Chemistry. - 1998. - Vol. 92, № 2. - С. 101-108 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: New fluorinated 2-arylhydrazones of 1,2,3-triketones, 2-arylhydrazone-1,2,3-diketo esters and 3-arylhydrazone-1,2,3,4-triketo esters have been prepared by the coupling of fluorine-containing 1,3-keto esters, 1,3-diketones, acyl(aroyl)pyruvic esters and their chelates with aryldiazonium chlorides. The arylhydrazones react with hydrazine hydrate, phenylhydrazine, thiosemicarbazide and hydroxylamine to form the corresponding pyrazole and isoxazole derivatives. Interaction of 3-arylhydrazone-1,2,3,4-diketo esters with o-phenylenediamine results in quinoxaline products. Intramolecular cyclization of the arylhydrazones with pentafluorophenyl substituents leads to cinnolone derivatives |
K 96 Kuzueva, O. G. Synthesis of 2-arylhydrazones of aliphatic fluorine-containing 1,2,3-tricarbonyl compounds and their reactions with dinucleophiles [Electronic resource] / O. G. Kuzueva, Ya. V. Burgart, V. I. Saloutin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1998. - Vol. 47, № 4. - P673-678 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: New fluorinated 2-arylhydrazones of 1,2,3-tricarbonyl compounds were obtained by coupling fluorine-containing 3-oxo esters, 1,3-diketones, and their copper chelates with aryldiazonium chlorides. Reactions of these arylhydrazones with hydrazine hydrate, phenylhydrazine, thiosemicarbazide, and hydroxylamine gave the corresponding pyrazole and isoxazole derivatives \\\\Expert2\\nbo\\Russian Chemical Bulletin\\1998, 47 (4), 673.pdf |
T 82 Transformations of C-adducts of 1,4-diazinium salts with dicarbonyl compounds into polycyclic systems [Electronic resource] / E. V. Verbitskiy, P. A. Slepukhin, G. L. Rusinov, V. N. Charushin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2008. - Vol. 57, № 3. - P652-656 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: C-Adducts of 5-(het)aryl-2,3-dicyano-1-pyrazinium salts containing a residue of a 1,3-dicarbonyl compound at position 6 can be involved in the cyclization with hydrazine hydrate giving rise to pyrazino[2,3-c]pyridazines along with the expected pyrazole derivatives. The reactions of the same ?H-adducts with hydroxylamine unexpectedly afforded triazacyclopenta[a]indene derivatives. The crystallographic data on the three-dimensional structures of new polycyclic compounds were obtained \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2008, 57 (3), 652.pdf |
K 96 Kuznetsova, O. A. Synthesis of fluorine-containing functionalized isoxazolines [Electronic resource] / O. A. Kuznetsova, V. I. Filyakova, K. I. Pashkevich // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1996. - Vol. 45, № 5. - P1245-1246 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The reaction of regioisomeric fluoroalkyl-containing (3-aminovinylketones with hydroxylamine generatedin situ from hydroxylamine sulfate, afforded 5-hydroxy- or 5-amino-5fluoroalkyl-2-isoxazolines \\\\Expert2\\nbo\\Russian Chemical Bulletin\\1996, 45 (5), 1245.pdf |
S 73 Sosnovskikh, V. Ya. A reinvestigation of the reactions of 3-substituted chromones with hydroxylamine. Unexpected synthesis of 3-amino-4H-chromeno[3,4-d]isoxazol-4-one and 3-(diaminomethylene)chroman-2,4-dione [Text] / V. Ya. Sosnovskikh, V. S. Moshkin, M. I. Kodess // Tetrahedron Letters. - 2008. - Vol. 49, № 48. - P6856-6859 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Reactions of 3-substituted chromones (3-formylchromone, 3-formylchromone-3-oxime, and 3-cyanochromone) with hydroxylamine in alkaline medium were reinvestigated, and a proof of structures and a probable reaction pathway are presented. Syntheses of 2-aminochromone-3-carboxamide, 3-amino-4H-chromeno[3,4-d]isoxazol-4-one, and 3-(diaminomethylene)chroman-2,4-dione were developed \\\\Expert2\\nbo\\Tetrahedron Letters\\2008, v. 49, p.6856.pdf |
R 30 Reaction of 2-(polyfluoroacyl)cycloalkanones with hydroxylamine [Text] / D. V. Sevenard, O. G. Khomutov, K. I. Pashkevich, E. Lork, G. -V. Roeschenthaler // Helvetica Chimica Acta. - 2002. - Т. 85, № 7. - P1960-1972. - Библиогр.: с. Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The 2-acylcycloalkanones 1a-g and 3a-c, possessing a polyfluoroalkyl group, react with hydroxylamine regio- and stereoselectively to yield 4,5-dihydroisoxazol-5-ols 2a-g and 4a-c, respectively, i.e., products of N-addition to the oxo group at the cycloalkane ring (Schemes 1 and 2). The products 2 and 4 can be dehydrated under drastic conditions only (Schemes 3 and 4). The structure of one of the 4,5-dihydroisoxazol-5-ols was confirmed by X-ray crystal-structure analysis |
S 98 Synthesis of 5-substituted 8,8-dimethyl-8,9-dihydro-3H,7H-[1,2]oxazino[5,4,3-de]quinolin-3-ones [Electronic resource] / D. A. Rudenko, P. A. Slepukhin, V. I. Karmanov, M. I. Vakhrin, S. N. Shurov, Yu. A. Shchurov // Chemistry of Heterocyclic Compounds. - 2013. - Vol.48, №10. - 1539-1544. Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): HYDROXYLAMINE -- QUANTUM-CHEMICAL CALCULATIONS -- TETRAHYDROQUINOLINE-4-CARBOXYLIC ACIDS Аннотация: The reaction of 2-substituted 7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-4-carboxylic acids with hydroxylamine results in the formation of 5-substituted 8,8-dimethyl-8,9-dihydro-3H,7H-[1,2]ox-azino[5,4,3-de]quinolin-3-ones. The structure of the 5-phenyl derivative has been established by X-ray structural analysis. A possible mechanism of the reaction has been proposed on the basis of nonempirical quantum-chemical calculations \\\\Expert2\\NBO\\Chemistry of Heterocyclic Compounds\\2013, v.48, N 10, p. 1539-1544.pdf |
A 10 A Convenient Approach to CF3-Containing N-Heterocycles Based on 2-Methoxy-2-methyl-5-(trifluoromethyl)furan-3(2H)-one [Electronic resource] / D. N. Bazhin, Yu. S. Kudyakova, G. -V. Roeschenthaler, Ya. V. Burgart, P. A. Slepukhin, M. L. Isenov, V. I. Saloutin, V. N. Charushin // European Journal of Organic Chemistry. - 2015. - № 23. - С. 5236-5245. - Bibliogr. : p. 5245 (23 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): NITROGEN HETEROCYCLES -- FLUORINE -- OXYGEN HETEROCYCLES Аннотация: New synthetic routes to trifluoromethylated N-heterocycles based on condensations of 2-methoxy-2-methyl-5-(trifluoromethyl)furan-3(2H)-one with bifunctional N-nucleophiles are described. For the first time, trifluoromethyl-containing pyrazoles, pyrazolines and isoxazolines bearing hydrazone or oxime groups could be obtained by a one-pot strategy based on reactions of 5-(trifluoromethyl)furan-3(2H)-one with two equivalents of the corresponding hydrazines or hydroxylamine in the presence of an acid. The interaction of furan-3(2H)-one with ureas proceeded under mild conditions to furnish 1H-furo[2,3-d]imidazol-2(3H)-one derivatives in good yield. Further, a trifluoromethyl-containing quinoxaline derivative was obtained by condensation of furan-3(2H)-one with ortho-phenylenediamine. \\\\expert2\\nbo\\European Journal of Organic Chemistry\\2015, №23. p.5236-5245.pdf |
S 98 Synthesis of 5-aryl-2-hydroxy-2-(trifluoromethyl)furan-3(2H)-ones and their reactions with aromatic 1,2-diamines, hydrazine & hydroxylamine / A. V. Safrygin, R. A. Irgashev, P. A. Slepukhin, G. -V. Roeschenthaler, V. Ya. Sosnovskikh // Tetrahedron. - 2015. - Vol. 71. - С. 8535-8543 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHESIS -- AROMATIC 1,2-DIAMINES -- HYDROXYLAMINE \\\\expert2\\NBO\\Tetrahedron\\2015, v. 71 , p. 8535.pdf |
An effective route to dithieno[3,2- B:2′,3′- D ]thiophene-based hexaheteroacenes / N. S. Demina, R. A. Irgashev, N. A. Kazin [et al.] // Synlett. - 2021. - Vol. 32, № 10. - P1009-1013 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): BENZOTHIENOTHIENOTHIENOINDOLES -- AMINOTHIOPHENES -- ARYLHYDRAZINES Аннотация: A series of 12H-[1]benzo[4′′,5′′]thieno[2′′,3′′:4′,5′]thieno[2′,3′:4,5]thieno[3,2-b]indoles were efficiently prepared in three steps starting from available benzo[b]thieno[2,3-d]thiophen-3(2H)-ones. These fused ketones were treated with the Vilsmeier reagent and hydroxylamine hydrochloride to give the corresponding 3-chlorobenzo[b]thieno[2,3-d]thiophene-2-carbonitriles, which then reacted with methyl sulfanylacetate to form methyl 3-aminobenzo[4′,5′]thieno[2′,3′:4,5]thieno[3,2-b]thiophene-2-carboxylates, in accordance with the Fiesselmann thiophene synthesis protocol. Finally, the desired N,S-heterohexacenes were obtained by conversion of these fused 3-aminothiophene-2-carboxylates into the corresponding 3-aminothiophene intermediates, which acted as synthetic equivalents of thiophen-3(2H)-ones, followed by their acid-promoted reaction with arylhydrazines, in accordance with the Fischer indolization procedure. |