cyclohexane-1

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Varlamov A.v. - One of the best experts on this subject based on the ideXlab platform.

  • Synthesis and conversions of substituted 4,5-dihydro-3H-spiro[benz-2-azepine-3,1′-cyclohexanes]
    'Springer Science and Business Media LLC', 2020
    Co-Authors: Varlamov A.v., Zubkov F.i., Lazareva E.v., Chernyshev A.i., Grudinin D.g.
    Abstract:

    On oxidizing substituted 1,2,4,5-tetrahydro-3H-spiro[benz-2-azepine-3,1′-cyclohexanes]with potassium permanganate under phase-transfer catalysis conditions the corresponding 4,5-dihydro derivatives are formed in quantitative yield. By the action of allyl- and benzylmagnesium halides 5-methyl-4,5-dihydro-3H-spiro[benz-2-azepine-3,1′-cyclohexane] is converted into 5-methyl-1,2,4,5- tetrahydro-1-allyl(benzyl)-3H-spiro[benz-2-azepine-3,1′-cyclohexane], and by reaction with phenoxyketene and dichlorocarbene into the corresponding 2-oxoazetidino[4,1-a]- and 1,1-dichloroaziridino[3,1-a]benz-2-azepines

  • Reactions of 4,5-dihydro-5-methyl-3H-spiro[benz-2-azepine-3-cyclohexane] N-oxide with some nucleophilic reagents
    Латвийский институт органического синтеза Латвийской академии наук Springer New York Consultants Bureau, 2020
    Co-Authors: Varlamov A.v., Chernyshev A.i., Grudinin D.g., Levov A.n., Golovtsov N.i., Borisov R.s.
    Abstract:

    4,5-Dihydro-5-methyl-3H-spiro[benz-2-azepine-3-cyclohexane] N-oxide reacted with cyanide ion and isopropyl magnesium bromide to give the corresponding 1-cyano- and 1-isopropyl-4,5-dihydro-5-methyl- 3H-spiro[benz-2-azepine-3-cyclohexane], but reaction with phenyl magnesium bromide, benzyl magnesium chloride, and nitromethane gave cyclic hydroxylamines: 1-substituted N-hydroxy-1,2,4,5-tetrahydro-5- methyl-3H-spiro[benz-2-azepine-3-cyclohexanes] which were oxidized to the corresponding nitrones

  • Synthesis of substituted and condensed tetrahydrospiro[benzo-2- azepinecyclohexanes] from 1-cyano- and 1-carbamoyl-5-methyl-4,5-dihydro-3H- spiro[benzo-2-azepine-3,1′-cyclohexanes]
    'Springer Science and Business Media LLC', 2020
    Co-Authors: Varlamov A.v., Chernyshev A.i., Grudinin D.g., Eganov A.a., Levov A.n.
    Abstract:

    Substitution of the nitrile group by hydroxylamine and hydrazine has been effected in 1-cyanodihydrospiro[benzo-2-azepine-3,1′-cyclohexane]. From the 1-cyano and 1-hydrazino derivatives tetrahydrospiro{1,2,3- and 1,2,4-triazolo[5,1-a]benzoazepine-5,1′-cyclohexanes} have been obtained. It was established that 1-carbamoyldihydrospiro[benzo-2-azepine-3,1′- cyclohexanes] are converted under the conditions of the Hoffmann reaction into spiro{diaziridino[3,1-a]benzo-2-azepine-3,1′-cyclohexane{, and is reduced by sodium borohydride to the tetrahydro derivative. ©2005 Springer Science+Business Media, Inc

  • Stereochemistry of the [3+2] cycloaddition of acrylonitrile to the N-oxide of 5-methyl-4,5-dihydro-3H-spiro[benz-2-azepine-3,1′-cyclohexane]
    Латвийский институт органического синтеза Латвийской академии наук Springer New York Consultants Bureau, 2020
    Co-Authors: Varlamov A.v., Zubkov F.i., Chernyshev A.i., Turchin K.f., Borisov R.s.
    Abstract:

    The [3+2] cycloaddition of acrylonitrile to the N-oxide of 5-methyl-4,5-dihydro-3H-spiro[benz-2- azepine-3,1′-cyclohexane] under conditions of both kinetic and thermodynamic control proceeds without regioselectivity or stereoselectivity with the formation of eight isomeric 1-cyano- and 2-cyano-7-methyl-1,2,4,6,7,11b-hexahydro-5H-spiro [isoxazolidino[3,2-a]benz-2-azepine-5,1′-cyclohexanes], six of which were isolated in an individual state. Their structure and stereochemistry were established by 1H NMR

  • Synthesis, chemical transformations, and structure of 1,2,3,4-tetrahydrospiro(quinoline-2-cycloalkanes)
    'Springer Science and Business Media LLC', 2020
    Co-Authors: Kuznetsov V.v., Varlamov A.v., Aliev A.e., Pal'ma A.r., Prostakov N.s.
    Abstract:

    The cyclization of 1-(m-toluidino)-1-allylcyclohexane under acid-catalysis conditions gave 4,5- and 4,7-dimethyl-1,2,3,4-tetrahydrospiro(quinoline-2-cyclohexanes). The bromination, nitration, N-acylation, and N-allylation of 4-methyl-1,2,3,4-tetrahydrospiro[quinoline-2-cyclohexane(cyclopentane)] were studied. It was established that nitration takes place In the 6 and 7 positions, while bromination occurs in the 6 and 8 positions. The amino-Claisen rearrangement of N-allyltetrahydroquinolines is accompanied by quantitative allyl-vinyl isomerization. The stereochemistry of the synthesized spiro(tetrahydroquinolinecycloalkanes) was studied by PMR spectroscopy. © 1992 Plenum Publishing Corporation

Joao Costa Pessoa - One of the best experts on this subject based on the ideXlab platform.

  • oxidovanadium iv complexes of tetradentate ligands encapsulated in zeolite y as catalysts for the oxidation of styrene cyclohexene and methyl phenyl sulfide
    European Journal of Inorganic Chemistry, 2011
    Co-Authors: Mannar R Maurya, Priyanka Saini, Amit Kumar, Joao Costa Pessoa
    Abstract:

    The reaction of oxidovanadium(IV)-exchanged zeolite-Y with N,N′-ethylenebis(pyridoxyliminato) (H2pydx-en, I), N,N′-propylenebis(pyridoxyliminato) (H2pydx-1,3-pn, II) and H2pydx-1,2-pn (III) in methanol heated at reflux leads to the formation of the corresponding complexes, abbreviated herein as [VIVO(pydx-en)]-Y (4), [VIVO(pydx-1,3-pn)]-Y (5) and [VIVO(pydx-1,2-pn)]-Y (6) in the supercages of zeolite-Y. The neat complexes [VIVO(pydx-en)] (1), [VIVO(pydx-1,3-pn)] (2) and [VIVO(pydx-1,2-pn)] (3) were also prepared. Spectroscopic studies (IR, UV/Vis and EPR), elemental analyses, thermal studies, field-emission scanning electron micrographs (FESEM) and X-ray diffraction patterns were used to characterize these complexes. Oxidations of styrene, cyclohexene and methyl phenyl sulfide were investigated using these complexes as catalyst precursors in the presence of H2O2 as oxidant. Under the optimized reaction conditions, a maximum of 85.5 % conversion of styrene was obtained with 4, 84.6 % conversion with 5 and 82.9 % conversion with 6 in 6 h of reaction time. The selectivity of the various products was similar for the catalyst precursors 4–6 and followed the order: benzaldehyde > 1-phenylethane-1,2-diol > benzoic acid > phenyl acetaldehyde. With cyclohexene, a maximum conversion of 95.9 % was achieved with 4, 94.5 % with 5 and 94.2 % conversion with 6, also in 6 h of reaction time. The selectivity of the various products was similar for the three catalysts: 2-cyclohexen-1-one > 2-cyclohexen-1-ol > cyclohexane-1,2-diol. The oxidation of methyl phenyl sulfide was achieved with 4, 5 and 6 in 2.5 h of reaction time with 85.5, 82.1 and 80 % conversion, with higher selectivity towards sulfoxide. Overall, the encapsulated catalysts were significantly more active than their neat counterparts and have the further advantage of being recyclable. No relevant difference in activity was found due to a change in the diamine in the Schiff base ligands I–III. UV/Vis and 51V NMR spectroscopic experiments with 1 confirmed the plausible formation of VVO(O2)L as intermediates in the catalytic oxidations.

  • immobilisation of oxovanadium iv dioxomolybdenum vi and copper ii complexes on polymers for the oxidation of styrene cyclohexene and ethylbenzene
    Applied Catalysis A-general, 2008
    Co-Authors: Mannar R Maurya, Pedro Adao, Aarti Arya, Joao Costa Pessoa
    Abstract:

    Abstract The reaction of 2-thiomethylbenzimidazole (Htmbmz) with chloromethylated polystyrene yielded a product designated by (PS-ligand), which corresponds mostly to the tmbmz bound to the polystyrene matrix by the sulfur atom. [VO(acac) 2 ], [MoO 2 (acac) 2 ] and Cu(CH 3 COO) 2 react with the PS-ligand to give PS-[VO(ligand) n ] ( 1 ), PS-[MoO 2 (ligand) n ] ( 2 ) and PS-[Cu(ligand) n ] ( 3 ), respectively, with n  ≈ 2. Non-polymer-bound complexes [VO(tmbmz) 2 ] ( 4 ), [MoO 2 (tmbmz) 2 ] ( 5 ) and [Cu(tmbmz) 2 ] ( 6 ) have also been prepared similarly. The anchored complexes were characterized by elemental analysis, IR, electronic and EPR spectroscopy, field-emission scanning electron micrograph (FE-SEM), energy dispersive X-ray analysis (EDAX) and thermo gravimetric studies and. EPR was particularly useful to characterize the binding modes in PS-[VO(ligand) n ] ( 1 ) and PS-[Cu(ligand) n ] ( 3 ), confirming that the vanadium and copper centers are well dispersed in the polymer matrix and supporting the presence of N 2 O 2 binding modes in both cases and the preservation of the binding mode at the end of the catalytic reactions carried out. The catalytic potential of these complexes was tested for the oxidation of styrene, cyclohexene and ethylbenzene using 30% H 2 O 2 as an oxidant. Various parameters, such as concentration of oxidant, amount of catalyst and temperature of the reaction mixture, have been optimized to obtain the maximum oxidation of substrates. Under the optimized reaction conditions, styrene gave three products with the selectivity order: benzaldehyde > 1-phenylethane-1,2-diol > styrene oxide. Oxidation of cyclohexene gave three products, the order of selectivity being: cyclohexane-1,2-diol > 2-cyclohexene-1-one > cyclohexeneoxide. At least four reaction products with the selectivity order: benzaldehyde > phenylacetic acid > acetophenone > 1-phenylethane-1,2-diol have been obtained on oxidation of ethylbenzene. The recycle ability of polymer-anchored metal complexes was checked; the results confirm that the polymer-bound complexes are not leached during the reaction/recovery procedures. Catalytic activities of the PS-supported complexes are higher than those of the corresponding non-polymer-bound complexes. Possible mechanisms are outlined and discussed. In all cases, peroxo or peroxy–metal complexes form; the formation of other intermediates is also discussed.

  • zeolite encapsulated copper ii complexes of pyridoxal based tetradentate ligands for the oxidation of styrene cyclohexene and methyl phenyl sulfide
    European Journal of Inorganic Chemistry, 2007
    Co-Authors: Mannar R Maurya, Baljit Singh, Pedro Adao, Fernando Avecilla, Joao Costa Pessoa
    Abstract:

    Interaction of copper(II)-exchanged zeolite-Y with N,N′-ethylenebis(pyridoxyliminato) (H2pydx-en, I) and N,N′-propylenebis(pyridoxyliminato) (H2pydx-1,3-pn, II) ligands in refluxing methanol leads to the formation of the corresponding complexes, abbreviated herein as [Cu(pydx-en)]-Y (3) and [Cu(pydx-1,3-pn)]-Y (4), in the supercages of zeolite-Y. The neat complexes, [Cu(pydx-en)] (1) and [Cu(pydx-1,3-pn)] (2), have also been prepared with these ligands. Spectroscopic studies (IR, UV/Vis and EPR), elemental analyses, thermal studies, field emission scanning electron micrographs (FE-SEM) and X-ray diffraction patterns have been used to characterise these complexes. The crystal and molecular structures of 1 and of 2·CH3OH, have been determined, confirming the ONNO binding mode of the ligands. The geometry around the metal ion is very slightly distorted square-planar in 1 and distorted square-pyramidal in 2. The encapsulated complexes catalyse the oxidation, by H2O2 and tert-butyl hydroperoxide, of styrene, cyclohexene and thioanisole efficiently. Under optimised reaction conditions, the oxidation of styrene catalysed by 3 and 4 gave 23.6 % and 28.0 % conversion, respectively, using tert-butyl hydroperoxide as oxidant, where styrene oxide, benzaldehyde, benzoic acid and phenylacetaldehyde are the major products. Better conversions have been obtained using H2O2 as oxidant. Oxidation of cyclohexene catalysed by these complexes gave cyclohexene oxide, 2-cyclohexen-1-ol, cyclohexane-1,2-diol and 2-cyclohexen-1-one as the major products. A maximum of 90.1 % conversion of cyclohexene with 3 and 83.0 % with 4 was obtained under optimised conditions. Similarly, a maximum of 80.3 % conversion of methyl phenyl sulfide with 3 and 81.0 % with 4 was observed, where the selectivity of the major product methyl phenyl sulfoxide was found to be about 60 %. Tests for the recyclability and heterogeneity of the reactions have also been carried out, and the results indicate their recyclability. A possible reaction mechanism has been proposed by titrating a methanol solution of 1 and 2 with H2O2 to identify the possible intermediates.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

Grudinin D.g. - One of the best experts on this subject based on the ideXlab platform.

  • Synthesis and conversions of substituted 4,5-dihydro-3H-spiro[benz-2-azepine-3,1′-cyclohexanes]
    'Springer Science and Business Media LLC', 2020
    Co-Authors: Varlamov A.v., Zubkov F.i., Lazareva E.v., Chernyshev A.i., Grudinin D.g.
    Abstract:

    On oxidizing substituted 1,2,4,5-tetrahydro-3H-spiro[benz-2-azepine-3,1′-cyclohexanes]with potassium permanganate under phase-transfer catalysis conditions the corresponding 4,5-dihydro derivatives are formed in quantitative yield. By the action of allyl- and benzylmagnesium halides 5-methyl-4,5-dihydro-3H-spiro[benz-2-azepine-3,1′-cyclohexane] is converted into 5-methyl-1,2,4,5- tetrahydro-1-allyl(benzyl)-3H-spiro[benz-2-azepine-3,1′-cyclohexane], and by reaction with phenoxyketene and dichlorocarbene into the corresponding 2-oxoazetidino[4,1-a]- and 1,1-dichloroaziridino[3,1-a]benz-2-azepines

  • Reactions of 4,5-dihydro-5-methyl-3H-spiro[benz-2-azepine-3-cyclohexane] N-oxide with some nucleophilic reagents
    Латвийский институт органического синтеза Латвийской академии наук Springer New York Consultants Bureau, 2020
    Co-Authors: Varlamov A.v., Chernyshev A.i., Grudinin D.g., Levov A.n., Golovtsov N.i., Borisov R.s.
    Abstract:

    4,5-Dihydro-5-methyl-3H-spiro[benz-2-azepine-3-cyclohexane] N-oxide reacted with cyanide ion and isopropyl magnesium bromide to give the corresponding 1-cyano- and 1-isopropyl-4,5-dihydro-5-methyl- 3H-spiro[benz-2-azepine-3-cyclohexane], but reaction with phenyl magnesium bromide, benzyl magnesium chloride, and nitromethane gave cyclic hydroxylamines: 1-substituted N-hydroxy-1,2,4,5-tetrahydro-5- methyl-3H-spiro[benz-2-azepine-3-cyclohexanes] which were oxidized to the corresponding nitrones

  • Synthesis of substituted and condensed tetrahydrospiro[benzo-2- azepinecyclohexanes] from 1-cyano- and 1-carbamoyl-5-methyl-4,5-dihydro-3H- spiro[benzo-2-azepine-3,1′-cyclohexanes]
    'Springer Science and Business Media LLC', 2020
    Co-Authors: Varlamov A.v., Chernyshev A.i., Grudinin D.g., Eganov A.a., Levov A.n.
    Abstract:

    Substitution of the nitrile group by hydroxylamine and hydrazine has been effected in 1-cyanodihydrospiro[benzo-2-azepine-3,1′-cyclohexane]. From the 1-cyano and 1-hydrazino derivatives tetrahydrospiro{1,2,3- and 1,2,4-triazolo[5,1-a]benzoazepine-5,1′-cyclohexanes} have been obtained. It was established that 1-carbamoyldihydrospiro[benzo-2-azepine-3,1′- cyclohexanes] are converted under the conditions of the Hoffmann reaction into spiro{diaziridino[3,1-a]benzo-2-azepine-3,1′-cyclohexane{, and is reduced by sodium borohydride to the tetrahydro derivative. ©2005 Springer Science+Business Media, Inc

Chernyshev A.i. - One of the best experts on this subject based on the ideXlab platform.

Borisov R.s. - One of the best experts on this subject based on the ideXlab platform.

  • Reactions of 4,5-dihydro-5-methyl-3H-spiro[benz-2-azepine-3-cyclohexane] N-oxide with some nucleophilic reagents
    Латвийский институт органического синтеза Латвийской академии наук Springer New York Consultants Bureau, 2020
    Co-Authors: Varlamov A.v., Chernyshev A.i., Grudinin D.g., Levov A.n., Golovtsov N.i., Borisov R.s.
    Abstract:

    4,5-Dihydro-5-methyl-3H-spiro[benz-2-azepine-3-cyclohexane] N-oxide reacted with cyanide ion and isopropyl magnesium bromide to give the corresponding 1-cyano- and 1-isopropyl-4,5-dihydro-5-methyl- 3H-spiro[benz-2-azepine-3-cyclohexane], but reaction with phenyl magnesium bromide, benzyl magnesium chloride, and nitromethane gave cyclic hydroxylamines: 1-substituted N-hydroxy-1,2,4,5-tetrahydro-5- methyl-3H-spiro[benz-2-azepine-3-cyclohexanes] which were oxidized to the corresponding nitrones

  • Stereochemistry of the [3+2] cycloaddition of acrylonitrile to the N-oxide of 5-methyl-4,5-dihydro-3H-spiro[benz-2-azepine-3,1′-cyclohexane]
    Латвийский институт органического синтеза Латвийской академии наук Springer New York Consultants Bureau, 2020
    Co-Authors: Varlamov A.v., Zubkov F.i., Chernyshev A.i., Turchin K.f., Borisov R.s.
    Abstract:

    The [3+2] cycloaddition of acrylonitrile to the N-oxide of 5-methyl-4,5-dihydro-3H-spiro[benz-2- azepine-3,1′-cyclohexane] under conditions of both kinetic and thermodynamic control proceeds without regioselectivity or stereoselectivity with the formation of eight isomeric 1-cyano- and 2-cyano-7-methyl-1,2,4,6,7,11b-hexahydro-5H-spiro [isoxazolidino[3,2-a]benz-2-azepine-5,1′-cyclohexanes], six of which were isolated in an individual state. Their structure and stereochemistry were established by 1H NMR

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