N 89 Novel fluorinated chromones [Text] / V. I. Saloutin, Z. E. Skryabina, I. T. Bazyl, O. N. Chupakhin // Journal of Fluorine Chemistry. - 1993. - Vol. 65, N 1-2. - P37-41 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The self-condensation of ethyl pentafluorobenzoylacetate leads to the formation of 3-pentafluorophenyl-1H-sopyrono[2,3-b]-6,7,8,9-tetrafluorochrom in 37% yeld. On hydrolysis, this gave 2-pentafluorobenzoylmethyl-5,6,7,8-tetrafluorochromone |
A 10 A new approach to the synthesis of fluorinated chromones [Electronic resource] / V. I. Saloutin, I. T. Bazyl, Z. E. Skryabina, V. M. Krokhalev, O. N. Chupakhin // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 1992. - Vol. 41, N 9. - P1714-1715 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The condensation of two molecules of ethyl pentafluorobenzoylacetate gives 1-oxo-3-penta fluorophenyl-1H-pyrano[4,3-b]6,7,8,9-tetrafluorochrome \\\\Expert2\\nbo\\Russian Chemical Bulletin\\1992, 41 (9), 1714.pdf |
C 91 Crystalline hydrogen-bonded adducts of dimethyl sulphoxide and 7-hydroxypolyfluoroquinolones (chromones [Text] / V. I. Saloutin, I. T. Bazyl, Z. E. Skryabina, G. G. Alexandrov, O. N. Chupakhin // Journal of Fluorine Chemistry. - 1995. - V. 74. - P15-19 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: A stable crystalline hydrogen-bonded adduct of dimethyl sulphoxide (DMSO) and 7-hydroxy-5,6,8-trifluoro-2-carboxychromone has been prepared by the reaction of 2-carboxy-5,6,7,8-tetrafluorochromone with KOH/glycerol in DMSO. It has been found that pentafluorophenol and also 1-cyclohexyl-7-hydroxy-5,6,8-trifluoro-4(1H)-4-oxoquinoline-2-carboxylic acid form the corresponding crystalline hydrogen-bonded adducts with DMSO. The structure of the latter has been established from an X-ray crystallographic study |
R 30 Reaction of Polyhaloalkyl-Substituted Chromones, Pyrones, and Furanones with Salicylaldehydes as a Direct Route to Fused 2H-Chromenes [Electronic resource] / V. Ya. Sosnovskikh, V. Yu. Korotaev, D. L. Chizhov, I. B. Kutyashev, D. S. Yachevskii, O. N. Kazheva, O. A. Dyachenko, V. N. Charushin // Journal of Organic Chemistry. - 2006. - Vol. 71, № 12. - P4538-4543 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Polyhaloalkyl-substituted chromones, Y-pyrones, and B-furanones react with salicylaldehydes in the presence of piperidine to give a wide variety of fused 2H-chromenes in good yields. This novel annulation reaction presumably proceeds by a tandem intermolecular oxa-Michael addition and subsequent intramolecular Mannich condensation. ?? \\\\Expert2\\nbo\\Journal of Organic Chemistry\\2006, v.71, N 12, p.4538.pdf |
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 |
S 83 Stereoselective hetero-Diels-Alder reaction of 3-(polyfluoroacyl)chromones with enol ethers. Novel synthesis of 2-R -containing nicotinic acid derivatives [Text] / V. Ya. Sosnovskikh, I. A. Khalymbadzha, R. A. Irgashev, P. A. Slepukhin // Tetrahedron. - 2008. - Vol. 64, № 44. - P10172-10180 : рис., табл. - Библиогр. : с. 10180 (15 назв.) Рубрики: ХИМИЧЕСКИЕ НАУКИ \\\\Expert2\\nbo\\Tetrahedron\\2008, v. 64, N44, p. 10172.pdf |
S 83 Stereoselective hetero-Diels-Alder reaction of 3-(trifluoroacetil)chromones with ceclic enol ethers: synthesis of 3-aroyl-2-(trifluoromethyl)pyridines with omega-hydroxyalkyl groups [Text] / V. Ya. Sosnovskikh, R. A. Irgashev, I. A. Khalymbadzha, P. A. Slepukhin // Tetrahedron Letters. - 2007. - Vol. 48, № 36. - P6297-6300 Рубрики: ХИМИЧЕСКИЕ НАУКИ \\\\Expert2\\nbo\\Tetrahedron Letters\\2007, v. 48, p.6297.pdf |
N 89 Novel chemical modifications at the 4-position of chromones. Synthesis and reactivity of 4H-chromene-4-spiro-5-isoxazolines and related compounds [Text] / V. Ya. Sosnovskikh, B. I. Usachev, A. Yu. Sizov, M. I. Kodess // Tetrahedron Letters. - 2004. - Vol. 45, № 39. - P7351-7354 : ил. - Библиогр.: с. 7353-7354 (22 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CHROMONES -- DILITHIOOXIMES -- 4H-CHROMENE-4-SPIRO-5'-ISOXAZOLINES; -- ALFA,BETA-UNSATURATED OXIMES -- BECKMANN REARRANGEMENT -- NITROSATION -- BROMINATION Аннотация: Reactions of chromones with dilithiooximes proceed via nucleophilic 1,2-addition to give, on acidification, 4H-chromene-4-spiro-5-isoxazoline derivatives in high yields. On treatment with concentrated H2SO4 the isoxazoline ring of this novel spiroannulated heterocyclic system opens to give alfa,beta-unsaturated oximes, which undergo nitrosation, bromination, and the Beckmann rearrangement to the corresponding spiroisoxazolines and alfa,beta-unsaturated amides, respectively. The latter can be obtained directly by the Beckmann rearrangement of 4H-chromene-4-spiro-5`-isoxazolines \\\\Expert2\\nbo\\Tetrahedron Letters\\2004, v. 45, p.7351.pdf |
R 30 Reactions of 4-hydroxy-5,6,7,8-tetrafluorocoumarin derivatives with S-nucleophiles [Text] / I. T. Bazyl, S. P. Kisil', Ya. V. Burgart, V. I. Saloutin // Journal of Fluorine Chemistry. - 2000. - Vol. 103, № 1. - P3-12 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: In the reactions with o-aminothiophenol, 4-hydroxy-(3-(imino)acetyl)-5,6,7,8-tetrafluorocoumarins give products of S-substitution at the C-7 atom. 7-Substituted 5,6,8-trifluorocoumarins form benzothiazole as a result of heterocyclic ring opening; 3-ethoxycarbonyl-2-methyl-5,6,7,8-tetrafluorochromone undergoes acid splitting to 2-(2-hydroxy-3,4,5,6-tetrafluorophenyl)benzothiazole. Under alkaline conditions, S-substituted coumarins decompose to acetophenone. In an acid medium, 4-hydroxy-3-iminoacetyl-5,6,8-trifluoro-7-(2-aminophenylthio)coumarin affords 7-(2-aminophenylthio)-2-methyl-5,6,8-trifluorochromone. 4-Hydroxy-5,6-difluoro-2-H-pyrano[6,5-a]phenothiazin-2-one was isolated from condensation of 7-(2-aminophenylthio)-4-hydroxy-5,6,8-trifluorocoumarin in the presence of NaH.????Reactions of 3-acetyl(iminoacetyl)-4-hydroxy-5,6,7,8-tetrafluorocoumarins and 3-ethoxycarbonyl-2-methyl-5,6,7,8-tetrafluorochromone with 2-mercaptoethanol result in the formation of 5,7,8-trisubstituted derivatives. Interaction of 3-ethoxycarbonyl-2-methyl-5,6,7,8-tetrafluorochromone with 2-mercaptoethanol, mercaptoacetic acid and 1,2-ethanedithiol leads to the formation of the 7-substituted products. Acyl-lactone rearrangement of mono- and trisubstituted chromones gives the corresponding coumarins.???? |
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 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 |
S 73 Sosnovskikh, V. Ya. Structural revision in the reactions of 3-cyanochromones with primary aromatic amines. Improved synthesis of 2-amino-3-(aryliminomethyl)chromones [Text] / V. Ya. Sosnovskikh, V. S. Moshkin, M. I. Kodess // Tetrahedron Letters. - 2009. - Vol. 50, № 47. - P6515-6518 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 3-Cyanochromones react with primary aromatic amines to give 2-amino-3-(aryliminomethyl)chromones as the sole products or as their mixtures with Z- and E-3-anilino-2-salicyloylacrylonitriles, depending on the reaction conditions. With aliphatic amines, 2-amino-3-(alkyliminomethyl)chromones are obtained in good yields. The reaction of 3-cyanochromone with o-phenylenediamine is reinvestigated and proof for the product structure and a possible reaction pathway are presented \\\\Expert2\\nbo\\Tetrahedron Letters\\2009, v. 50, p.6515.pdf |
R 30 Reaction of Polyhaloalkyl-Substituted Chromones, Pyrones, and Furanones with Salicylaldehydes as a Direct Route to Fused 2H-Chromenes [Text] : доклад, тезисы доклада / V. Ya. Sosnovskikh, V. Yu. Korotaev, D. L. Chizhov, I. B. Kutyashev, D. S. Yachevskii, V. N. Charushin // 18th ISFC international Symposium on Fluorine Chemistry. Bremen, 30th Jul.-4 Aug. 2006 г. : Final Program. Abstracts. - Bremen, 2006. - P307 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): GAMMA-RYRONES -- BETA-FURANONES |
S 53 Shcherbakov, K. V. Transformations of 5,6,7,8-tetrafluoro-2-ethoxycarbonylchromone under the action of primary amines [Electronic resource] / K. V. Shcherbakov, Ya. V. Burgart, V. I. Saloutin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2009. - Vol. 45, № 5. - P766-772 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 5,6,7,8-TETRAFLUORO -- CHROMONES Аннотация: 5,6,7,8-Tetrafluoro-2-ethoxycarbonylchromone in aprotic polar solutions formed by nucleophilic aromatic ipso-substitution 7-alkyl(aryl)amino-5,6,8-trifluorochromones. This transformation in ethanol depended on the reactivity of the acting amine: with stronger nucleophiles, aliphatic amines, an opening of the ?-pyrone ring occurred, with aromatic amines 7-monosubstituted chromones were the main products, and the open-chain esters formed in lesser amount \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2009, 45 (5), 766.pdf |
K 49 Kisil', S. P. New Fluoroaryl-containing beta,beta'-Dioxoesters in the Synthesis of Fluorobenzopyran-2(4)-ones [Electronic resource] / S. P. Kisil', Ya. V. Burgart, V. I. Saloutin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2001. - Vol. 37, № 10. - P1455-1462 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: For the first time were obtained ethyl 2-(2-methoxy-3,4,5,6-tetrafluorobenzoyl)-3-oxobutanoate and ethyl 2-pentafluorobenzoyl-3-oxobutanoate and their copper chelates. The compounds were prepared by acylation of ethyl acetoacetate with 2-methoxy-3,4,5,6-tetrafluoro- and pentafluorobenzoyl chlorides. Cyclization of these ,'-dioxoesters afforded substituted chromones. 2-Methyl-5-methoxy-6,7,8-trifluoro-3-ethoxycarbonylchromone hydrolyzes depending on reaction conditions either to 5-hydroxy-2-methyl-6,7,8-trifluorochromone or to 5-hydroxy-2-methyl-6,7,8-trifluorochromone-3-carboxylic acid. Reaction with morpholine provided 7-substituted product, and with aqueous ammonia as a result of rearrangement forms 3-acetimidoyl-4-hydroxy-5-methoxy-6,7,8-trifluorocoumarin. Hydrolysis of the latter yields 3-acetyl-4-hydroxy-5-methoxy-6,7,8-triflu \\\\Expert2\\nbo\\Russian Journal of Organic Chemistry\\2001, 37 (10), 1455.pdf |
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 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 |
S 73 Sosnovskikh, V. Ya. 2-Polyfluoroalkylchromones. 12. Nitration of 5,7-dimethyl-2-polyhaloalkylchromones and complete assignment of signals in the 1H and 13C NMR spectra of 5,7-dimethyl-2-trifluoromethylchromone and its mono- and dinitro derivatives [Electronic resource] / V. Ya. Sosnovskikh, B. I. Usachev, M. I. Kodess // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2002. - Vol. 51, № 10. - P1817-1828 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: The nitration of 5,7-dimethyl-2-polyhaloalkylchromones affords either 5,7-dimethyl-6-nitro- or 5,7-dimethyl-6,8-dinitro-2-polyhaloalkylchromones, depending on the reaction conditions. Signals in the 1H and 13C NMR spectra of the sterically hindered chromones were completely assigned using the 2D NOESY, HETCOR, and COLOC spectra. The influence of nonplanar nitro groups on chemical shifts of carbon atoms was studied. Some spectral peculiarities of the peri-methyl group were revealed. The 1H-1H and 13C-1H spin-spin coupling constants, including the extreme six-bond long-range coupling between the protons of the Me(5) group and H(8), were determined \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2002, 51 (10), 1817.pdf |
R 30 Reaction of 3-(polyfluoroacyl)chromones with hydrazines: new regioselective synthesis of RF-containing pyrazoles [Electronic resource] / V. Ya. Sosnovskikh, R. A. Irgashev, V. S. Moshkin, M. I. Kodess // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2008. - Vol. 57, № 10. - P2146-2155 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: Reactions of 3-(polyfluoroacyl)chromones with hydrazine, methyl-and phenylhydrazines proceed by the mechanism of nucleophilic 1,4-addition with subsequent pyrone ring opening and heterocyclization at the polyfluoroacyl group to 4-(2-hydroxyaroyl)-3-polyfluoro-alkylpyrazoles or at the aroyl group to 4-polyfluoroalkyl-2,4-dihydrochromeno[4,3-c]pyrazol-4-ols. Regiochemistry of the products was established based on the data of 2D-experiments HSQC, HMBC, and NOESY and X-ray diffraction study \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2008, 57 (10), 2146.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 |
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 73 Sosnovskikh, V. Ya. Reactions of 3-cyanochromones with primary amines: structures of the products [Electronic resource] / V. Ya. Sosnovskikh, V. S. Moshkin, M. I. Kodess // Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya). - 2010. - Vol. 59, № 3. - P615-625 Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): 3-CYANOCHROMONES -- PRIMARY AMINES -- RECYCLIZATION Аннотация: Reactions of 3-cyanochromones with primary aromatic amines in boiling benzene gave mixtures of Z- and E-3-arylamino-2-(2-hydroxyaroyl)acrylonitriles and 2-amino-3-(aryl-iminomethyl)chromones. The latter can easily be obtained in the individual state when the reaction is carried out in the presence of triethylamine. In the case of primary aliphatic amines, the open-chain reaction product immediately undergoes cyclization into 3-alkyliminomethyl-2-aminochromones. The structures of the products were examined by 1D and 2D 1H, 13C, and 15N NMR spectroscopy in DMSO-d6 and CDCl3 \\\\Expert2\\nbo\\Russian Chemical Bulletin\\2009, 59 (3), 615-625.pdf |