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Публикации Чарушина В.Н. (1)

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Общее количество найденных документов : 9
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   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.)

ББК 54
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
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   F 70


    Fluoroaryl containing beta,beta-dioxoesters in the synthesis of fluorobenzopyran-4(2)-ones [Text] / S. P. Kisil', Ya. V. Burgart, V. I. Saloutin, O. N. Chupakhin // Journal of Fluorine Chemistry. - 2001. - Vol. 108, № 2. - P125-131

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Fluoroaryl containing ?,??-dioxoesters and their copper(II) chelates have been prepared by acylation of ethyl acetoacetate with 2,6-dimethoxy-3,4,5-trifluorobenzoyl, 2-methoxy-3,4,5,6-tetrafluorobenzoyl and pentafluorobenzoyl chlorides. Cyclization of these ?,??-dioxoesters leads to formation of substituted fluorochromones. Depending on conditions, 2-methyl-5-methoxy-6,7,8-trifluoro-3-ethoxycarbonylchromone hydrolyzed to 5-hydroxy-2-methyl-6,7,8-trifluorochromone or 5-hydroxy-2-methyl-6,7,8-trifluorochromone-3-carboxylic acid. The same chromone reacts with morpholine to form a seven-substituted product and ammonium hydroxide to give 3-iminoacetyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin. Hydrolysis of the latter affords 3-acetyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin. Ethyl-2-(2,6-dimethoxy-3,4,5-trifluorobenzoyl)-3-oxobutanoates undergoes ketone-splitting to 1-(2,6-dimethoxy-3,4,5-trifluorophenyl)-1,3-butandione????

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   S 73

    Sosnovskikh, V. Ya.
    One-pot three-component reaction of 3-(polyfluoroacyl)chromones with active methylene compounds and ammonium acetate: regioselective synthesis of novel RF-containing nicotinic acid derivatives [Text] / V. Ya. Sosnovskikh, R. A. Irgashev, M. I. Kodess // Tetrahedron. - 2008. - Vol. 64, № 13. - P2997-3004

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
THREE-COMPONENT REACTIONS -- AMMONIUM ACETATE
Аннотация: Reactions of 3-(polyfluoroacyl)chromones with acetoacetamide and ethyl acetoacetate in the presence of ammonium acetate proceed at the C-2 atom of the chromone system with pyrone ring-opening and subsequent cyclization to 5-salicyloyl-2-methyl-6-(trifluoromethyl)nicotinamides, ethyl 5-salicyloyl-2-methyl-6-(trifluoromethyl)nicotinates, and ethyl 5-hydroxy-2-methyl-5-(polyfluoroalkyl)-5H-chromeno[4,3-b]pyridine-3-carboxylates. Similar reaction with ?-aminocrotononitrile gave 5-hydroxy-2-methyl-5-(polyfluoroalkyl)-5H-chromeno[4,3-b]pyridine-3-carbonitriles????

\\\\Expert2\\nbo\\Tetrahedron\\2008, v. 64, N13, p. 2997.pdf
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   R 30


    Reactions of ethyl 5,6,7,8-tetrafluoro-2-methylchromone-3-carboxylate and 3-acetimidoyl-5,6,7,8-tetrafluoro-4-hydroxycoumarin with S-nucleophiles [Electronic resource] / I. T. Bazyl, S. P. Kisil', S. N. Frolov, Ya. V. Burgart, V. I. Saloutin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1999. - Vol. 48, № 8. - P1537-1541

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The reactions of ethyl 5,6,7,8-tetrafluoro-2-methylchromone-3-carboxylate with mercaptoacetic acid and 1,2-ethanedithiol afforded C(7)-substitution products. The above-mentioned chromone reacted with 2-mercaptoethanol to yield 7-mono- or 5,7,8-trisubstituted products depending on the reaction conditions. The reaction of 3-acetimidoyl-5,6,7,8-tetrafluoro-4-hydroxycoumarin with 2-mercaptoethanol afforded a 5,7,8-trisubstituted produect. The acyl-lactone rearrangement of mono- and trisubstituted chromones yielded the corresponding coumarins

\\\\Expert2\\nbo\\Russian Chemical Bulletin\\1999, 48 (8), 1537.pdf
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   F 70


    Fluorine-containing Heterocycles. X. Acetoacetamides in the Synthesis of Fluorine-containing Chromone [Electronic resource] / G. N. Lipunova, E. V. Nosova, M. I. Kodess, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2004. - Vol. 40, № 8. - P1162-1166

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Fluorine-containing chromone-3-carboxamides were synthesized by reaction of tetra(penta)fluoro-benzoyl chlorides with acetoacetamides in dichloromethane in the presence of triethylamine. Nucleophilic substitution of fluorine atoms by amine rests in compounds synthesized was investigated

\\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2004, 40 (8), 1162.pdf
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   S 53

    Shcherbakov, K. V.
    Reactions of 2(3)-ethoxycarbonyl-5,6,7,8-tetrafluorochromones with methylamine [Electronic resource] / K. V. Shcherbakov, Ya. V. Burgart, V. I. Saloutin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2005. - Vol. 54, № 9. - P2157-2162. - Bibliogr. : p. 2162 (18 ref.)

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
CHROMONE -- METHYLAMINE -- NUCLEOPHILIC SUBSTITUTION -- RING OPENING
Аннотация: 2-Ethoxycarbonyl-5,6,7,8-tetrafluorochromone reacts with methylamine differently, depending on the solvent nature and the amount of the amine: in DMSO and MeCN, the fluorine atom at the C(7) atom is initially replaced and then the C(2) and/or C(9) are attacked, while in ethanol, the reaction involves the C(2) atom with opening of the pyrone ring. The reaction of 3-ethoxycarbonyl-5,6, 7,8-tetrafluoro-2-methylchromone with methylamine results, regardless of the solvent, in opening of the chromone ring and the formation of intermediate ethyl 3-(3,4,5,6-tetrafluoro-2-hydroxyphenyl)-2-(1-methylamino)ethylidene-3- oxopropionate, which undergoes intramolecular cyclization to give 5,6,7,8-tetrafluoro-3-(1-methylamino)ethylidene-3,4-dihydro-2H-benzopyran-2, 4-dione.

\\\\Expert2\\nbo\\Russian Chemical Bulletin\\2005, 54 (9), 2157-2162.pdf
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   R 30


    Reactions of 2-ethoxycarbonyl(carboxy)-5,6,7,8-tetrafluorochromones with N-nucleophiles [Electronic resource] / V. I. Saloutin, I. T. Bazyl, Z. E. Skryabina, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1994. - Vol. 43, № 5. - P849-853

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
2-ETHOXYCARBONYL(CARBOXY)-5,6,7,8-TETRAFLUOROCHROMONES -- N-NUCLEOPHILES -- ETHYLENEDIAMINE -- AMINES -- NUCLEOPHILIC REPLACEMENT
Аннотация: The direction of reactions of 2-ethoxycarbonyl-5,6,7,8-tetrafluoro- and 2-carboxy-5,6,7,8-tetrafluorochromones with ammonia, methylamine, hexylamine, and aniline depends on the inductive effect of the substituent at position C-2 of the chromone and on the basicity of the amine. Nucleophilic aromatic substitution of a fluorine atom takes place in the interaction of 2-ethoxycarbonyl-5,6,7,8-tetrafluorochromone with secondary amines (morpholine, N-methylpiperazine) and ethylenediamine.

\\\\Expert2\\nbo\\Russian Chemical Bulletin\\1994, 43 (5), 849.pdf
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   S 53

    Shcherbakov, K. V.
    Features of reactions of polyfluorinated ethyl 4-oxo-2-pnenyl-4H-chromene-3-carboxylates with N-nucleophiles [Electronic resource] / K. V. Shcherbakov, Ya. V. Burgart, V. I. Saloutin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2013. - Vol.49, №5. - С. 719-729. - Библиогр.: с. 729 (13 ref.)

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
BENZYLAMINE -- CHROMONE-COUMARIN REARRANGEMENT -- TETRAFLUOROFLAVONES
Аннотация: Ethyl 5,6,7,8-tetrafluoro-4-oxo-2-phenyl-4H-chromene-3-carboxylate in reactions with primary amines is characterized by a chromone-coumarin rearrangement affording 3-[amino(phenyl)methylene]-6,7,8-trifluoro-2H-chromene-2,4(3H)-diones, and ethyl 4-oxo-2-phenyl-5,6,7,8-tetrafluoro-4H-chromene-3-carboxylate characteristically adds the amine at the C2 site of the flavone furnishing 3-amino-3-phenyl-2-(2,3,4,5-tetrafluoro-6-hydroxybenzoyl)acrylates which depending on the substituent at the amino group are capable of intramolecular cyclization into 3-[(alkylamino)(phenyl)methylene]-5,6,7,8-tetrafluoro-2H-chromene-2,4(3H)-dione or in the case of benzylamine substituent, into ethyl 1-benzyl-5-hydroxy-4-oxo-2-phenyl-6,7,8-trifluoro-1,4-dihydroquinoline-3-carboxylate. The main process in the reaction of tri- and tetrafluoroflavones with secondary amine (1-methylpiperazine) is the nucleophilic substitution at the C7 of flavone. In the reaction with 1,2-phenylenediamine 3-[(2-aminophenyl)amino]-3-phenyl-2-(2,3,4,5-tetrafluoro-6-hydroxybenzoyl)acrylate was obtained from tetrafluoroflavone and 1H-benzimidazol-2-yl(3,4,5-trifluoro-2-hydroxyphenyl)methanone, from trifluoroflavone

\\\\expert2\\NBO\\Russian Journal of Organic Chemistry\\2013, 49, (5), 719-729.pdf
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   N 89


    Novel 3-acetyl-2-methyl-polyfluorochromones in reactions with amines and esters of amino acids [Electronic resource] / K. V. Shcherbakov, D. N. Bazhin, Ya. V. Burgart, V. I. Saloutin // Chemistry of Heterocyclic Compounds. - 2015. - Vol. 51, № 11/12. - С. 961-968. - Bibliogr. : p. 967-968 (21 ref.)

ББК 54
Рубрики: ХИМИЧЕСКИЕ НАУКИ
Кл.слова (ненормированные):
AMINE -- ACYLATION -- CHROMONE
Аннотация: Novel 3-acetyl-2-methyl-polyfluoro-4Н-chromen-4-ones were obtained via one-pot acylation of acetylacetone with polyfluorobenzoyl chlorides. These chromones were shown to form N-substituted 3-amino-1-[2-hydroxy(polyfluoro)phenyl]but-2-en-1-ones in reaction with aliphatic primary amines, esters of amino acids, and aqueous ammonia via opening of the pyrone ring and deacylation

\\\\expert2\\nbo\\Chemistry of Heterocyclic Compounds\\2015, v.51, N 11-12, p. 961-968.pdf
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