- Regiospecific Oxidation of Methyl Groups in Dimethylanisoles
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Dimethylanisoles in which one of the methyl groups is meta and the other is ortho or para are regiospecifically oxidized in high yield to the corresponding ortho- and para-substituted aldehydes by copper(II) and peroxydisulfate.Subsequent oxidation of the
- Hauser, Frank M.,Ellenberger, Suzanne R.
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- Selective Electrochemical Oxygenation of Alkylarenes to Carbonyls
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An efficient electrochemical method for benzylic C(sp3)-H bond oxidation has been developed. A variety of methylarenes, methylheteroarenes, and benzylic (hetero)methylenes could be converted into the desired aryl aldehydes and aryl ketones in moderate to excellent yields in an undivided cell, using O2 as the oxygen source and lutidinium perchlorate as an electrolyte. On the basis of cyclic voltammetry studies, 18O labeling experiments, and radical trapping experiments, a possible single-electron transfer mechanism has been proposed for the electrooxidation reaction.
- Li, Xue,Bai, Fang,Liu, Chaogan,Ma, Xiaowei,Gu, Chengzhi,Dai, Bin
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supporting information
p. 7445 - 7449
(2021/10/02)
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- Volatiles from the xylarialean fungus Hypoxylon invadens
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The volatiles emitted by agar plate cultures of the xylarialean fungus Hypoxylon invadens were investigated by use of a closed loop stripping apparatus in combination with GC-MS. Several aromatic compounds were found that could only be identified by comparison to all possible constitutional isomers with different ring substitution patterns. For the set of identified compounds a plausible biosynthetic scheme was suggested that gives further support for the assigned structures.
- Dickschat, Jeroen S.,Wang, Tao,Stadler, Marc
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p. 734 - 746
(2018/04/16)
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- Chemoselective oxidation and deprotection of para-methoxybenzylic position with (diacetoxyiodo)benzene in acetic-trifluoroacetic acid
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(Diacetoxyiodo)benzene in the presence of acetic–trifluoroacetic acid in THF has been developed for the chemoselective para-methoxybenzylic C–H bond oxidation to provide aryl carbonyl compounds at room temperature. The reaction condition is also applicable for the chemoselective deprotection of para-methoxybenzyl (PMB) ether in the presence of benzyl ether.
- Lin, Chun-Yu,Yang, Ping-Shin,Chou, Pang-Yu,Ong, Chi Wi
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p. 365 - 367
(2018/01/01)
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- A 4-methoxy-2-methyl-benzyl cyanide synthesis method
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The invention relates to a synthesis method for 4-methoxy-2-methyl benzyl cyanide. The synthesis method takes 3, 4-dimethylphenol which is cheap and simple and easy to purchase as the raw material, and comprises six steps: methylation, oxidation, Witting reaction, alkene ether hydrolysis, oximation and dehydration. The synthesis method uses the simple and cheap raw material, is simple to operate, is easy for industrial production, has short production cycle, only needs purification in the last step of the six so as to obtain high-quality 4-methoxy-2-methyl benzyl cyanide, and avoids using extremely toxic substances like NaCN and KCN, thus filling the blank home and abroad.
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- Synthesis of novel structurally simplified estrogen analogues with electron-donating groups in ring A
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A library of 25 novel estrogen analogues were prepared in five to eight steps from mostly commercially available substituted anisoles via bromination, formylation, Corey-Fuchs reaction, elimination, and Sonogashira reaction. Georg Thieme Verlag Stuttgart.
- Tietze, Lutz F.,Vock, Carsten A.,Krimmelbein, Ilga K.,Nacke, Linda
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experimental part
p. 2040 - 2060
(2009/12/27)
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- BICYCLIC DERIVATIVES AS PPAR MODULATORS
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The present invention is directed to compounds represented by the following structural formula, Formula (I), and stereoisomers, pharmaceutically acceptable salts, solvates and hydrates thereof, wherein: (a) R2 is selected from the group consisting of C0-C8 alkyl and C1-4- heteroalkyl; (b) X is selected from the group consisting of a single bond, O, S, S(O)2 and N; (c) U is an aliphatic linker wherein one carbon atom of the aliphatic linker is optionally replaced with O, NH or S, and wherein such aliphatic linker is optionally substituted with from one to four substituents each independently selected from R30; (d) Y is selected from the group consisting of C, O, S, NH and a single bond; and (e) E is C(R3)(R4)A or A.
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Page/Page column 60
(2008/06/13)
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- FUSED HETEROCYCLIC DERIVATIVES AS PPAR MODULATORS
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The present invention is directed to compounds represented by the following structural formula, Formula I: wherein (a) X is selected from the group consisting of a single bond, O, S. S(O)2 and N; (b) U is an aliphatic linker; (c) Y is selected from the group consisting of C, O, S, NH and a single bond; (d) E is C(R3) (R4)A or A and wherein (i) A is selected from the group consisting of carboxyl, tetrazole, C1-C6 alkylnitrile, carboxamidek, sulfonamide and acylsulfonamide; (e) B is selected from the group consisting of S, O, C, and N; (f) Z is selected from the group consisting of N and C; with the proviso that when B is C then Z is N.
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- Cycloalkyl alkanoic acids as integrin receptor antagonists derivatives
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The present invention relates to a class of compounds represented by the Formula I or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of the Formula I, and methods of selectively inhibiting or antagonizing the αvβ3 and/or αvβ5 integrin.
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- De novo design, synthesis, and evaluation of novel nonsteroidal phenanthrene ligands for the estrogen receptor
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Although there are many estrogen receptor antagonists with improved tissue selectivity profiles compared with tamoxifen, optimal tissue selectivity has not yet been demonstrated. As such there is still a need for additional diversity and new chemical scaf
- Schmidt, Jonathan M.,Mercure, Julie,Tremblay, Gilles B.,Pagé, Martine,Kalbakji, Aida,Feher, Miklos,Dunn-Dufault, Robert,Peter, Markus G.,Redden, Peter R.
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p. 1408 - 1418
(2007/10/03)
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- NAPTHTHALENE DERIVATIVES WHICH INHIBIT THE CYTOKINE OR BIOLOGICAL ACTIVITY OF MACROPHAGE MIGRATION INHIBITORY FACTOR (MIF)
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Where Y, R1-R8 and R101-R108 are as defined in the specification. Compounds of formula (II) and methods of inhibiting the cytokine or biological activity of Macrophage Migrating Inhibitory Factor (MIF) comprising contacting MIF with a compound of formula (I) are provided. The invention also relates to methods of treating diseases or conditions where MIF cytokine or biological activity is implicated comprising administration of compounds of formula (I), either alone or as part of a combination therapy.
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- Non-steroidal estrogen receptor ligands
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Novel non-steroidal estrogen receptor ligands and methods of synthesis are disclosed. The novel molecules are intended for use in therapeutic preparations for the treatment of estrogen receptor related disease states. The compounds specified are tetra-cyc
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- Some evidence in favour of an electron transfer mechanism in the TiO2 photosensitized oxidation of benzyl derivatives in aqueous media
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The structure and/or distribution of products from the TiO2-sensitized photooxidation of some benzyl derivatives in aerated and/or deaerated aqueous media and in the presence of Ag2SO4 are reported. The results suggest that the single electron transfer process from the substrate to the photogenerated hole, previously proposed in CH3CN, should also be operative on gradually going from aqueous CH3CN to pure water.
- Ranchella, Michele,Rol, Cesare,Sebastiani, Giovanni V.
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p. 311 - 315
(2007/10/03)
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- TiO2-catalyzed photooxygenation of methylaromatic compounds in the presence of Ag2SO4 in CH3CN
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Methylaromatic compounds have been photooxygenated in CH3CN, at room temperature, in the presence of TiO2 and Ag2SO4, to form benzaldehydes and, in some cases, benzoic acids, in yields up to 50%.
- Baciocchi,Rosato,Rol,Sebastiani
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p. 5437 - 5440
(2007/10/02)
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- Ring-Substituted y1,2-Bis(4-hydroxyphenyl)ethylenediamine>dichloroplatinum(II) Complexes: Compounds with a Selective Effect on the Hormone-Dependent Mammary Carcinoma
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dichloroplatinum(II) complexes with one substituent in the 2-position (CH3, CF3, F, Br, I: meso- and dl-1-PtCl2, meso-(3-5)-PtCl2, meso-(7 and 8)-PtCl2) or two substituents in the 2,6-position (CH3, Cl: meso-2-PtCl2, meso- and dl-6-PtCl2) in both benzene rings were synthesized and tested for estrogenic and toxic activities.Two complexes (meso-6-PtCl2 and meso-7-PtCl2) possess both effects.In comparative tests on estrogen receptor positive and negative mammary tumors in cell culture (MCF 7, ER+ and MDA-MB 231, ER-) and in animals (MXT, ER+ and MXT, ER-, mouse), meso-6-PtCl2 shows a selective effect on the estrogen receptor positive mammary carcinoma.A further increase of efficacy was achieved with the water-soluble (sulfato)platinum(II) derivative (meso-6-PtSO4).On the DMBA-induced hormone dependent mammary carcinoma of the SD rat, meso-6-PtSO4 is significantly more active than its ligand (meso-6) and cisplatin.
- Karl, Johann,Gust, Ronald,Spruss, Thilo,Schneider, Martin R.,Schoenenberg, Helmut,et al.
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- SUBSTITUENT EFFECTS ON THE PHOTOCHEMISTRY OF o-TOLUALDEHYDES
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The effect of 4-oxy and 4,5-dioxy substituents on the photochemical conversion of 2-methylbenzaldehydes to o-quinodimethanes (o-QDMs) has been studied.The presence of a 4-methoxy, or a 4 and 5-methoxy substituent prevented the photochemical formation of the o-QDM whereas 4-acetoxy and 4,5-diacetoxy-2-methylbenzaldehyde and the corresponding mesylates and tosylates were successfully converted to the o-QDMs.
- Charlton, James L.,Koh, Kevin
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p. 5595 - 5598
(2007/10/02)
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- Synthesis of 4-Hydroxy-2-methylbenzoic Acid and Its Higher Homologues
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Synthesis of 4-hydroxy-2-methylbenzoic acid (1a) and its higher homologues such as 4-hydroxy-2-methylphenylacetic acid (1b), 3-(4-hydroxy-2-methylphenyl)propanoic acid (1c) and 4-(4-hydroxy-2-methylphenyl)butanoic acid (1d) are described.
- Sen, P. K.,Pal, Panchanan,Goswami, Shyamaprosad,Chattopadhyay, Gautam
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p. 679 - 682
(2007/10/02)
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- Ortho Metalation Directed by α-Amino Alkoxides
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The addition of aromatic aldehydes to certain lithium dialkylamides in benzene or tetrahydrofuran gave α-amino alkoxides which were ortho lithiated with excess n-butyllithium.Subsequent alkylation and hydrolysis provided ortho-substituted aromatic aldehydes via a one-pot reaction.The ortho metalation of α-amino alkoxides derived from 1- and 2-naphthaldehyde and various substituted benzaldehydes was examined.When N,N,N'-trimethylethylenediamine was used as the amine component of the α-amino alkoxide, metalation could be carried out at lower temperatures.This rate increase is due to an intramolecular TMEDA-like assisted metalation.The synthetic utility of this ortho metalation, including how varying the amine component of the α-amino alkoxide affects the regiochemistry and metalation rate, is discussed.
- Comins, Daniel L.,Brown, Jack D.
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p. 1078 - 1083
(2007/10/02)
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- Organoiron Complexes in Organic Synthesis. Part 27. Synthesis and Reactivity of Tricarbonyliron Derivatives of 1,2-Disubstituted 4-Alkoxycyclohexadienylium Cations
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The synthesis, and reactions with stable enolate nucleophiles, of 1,2-disubstituted 4-alkoxycyclohexadienylium(tricarbonyl)iron complexes (3a), (3b), (3c), and (3d) is described.Only the 1,2-dimethyl-4-isopropoxycyclohexadienylium complex (3b) was found to react with nucleophiles with sufficiently high regioselectivity to allow a useful method of preparation of 3,4,4-trisubstituted cyclohexenones.
- Pearson, Anthony J.,Perrior, Trevor R.,Griffin, David A.
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p. 625 - 631
(2007/10/02)
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- Indirect Electrooxidation (an Ex-Cell Method) of Alkylbenzenes by Recycle Use of (NH4)2Ce(NO3)6 in Various Solvent Systems
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Indirect electrooxidation (an ex-cell method) of the side chain of alkylbenzenes has been performed by recycle use of (NH4)2Ce(NO3)6 (CAN) in various solvent systems.The side-chain oxidation of p-methoxytoluene (1) with CAN in methanol proceeds smoothly, yielding anisaldehyde (3, 94percent), while use of aqueous methanol or acetic acid resulted in a mixture of 3 and the dimeric product 4 (19-35percent) along with complex products (28-47percent).Electrooxidation of the recovered cerium(III) salts was perfomed smoothly in methanol by passing 1.1-1.2 F/mol of electricity to give a reddish methanol solution of CAN, which can be used for the next oxidation of 1.The repeated use of CAN over 10 times produced the desired 3 in over 90percent yields.Similarly, the oxidation of alkylbenzenes, bearing p-methoxy group, gave the corresponding side-chain-oxidized products.In contrast, p-tert-butyltoluene (9e) could be oxidized by heating with CAN in aqueous 50percent acetic acid at 85-90 deg C to give p-tert-butylbenzaldehyde in over 90percent yield.The regeneration of CAN after the oxidation of 9e was also accomplished by electrolysis in the aqueous 50percent acetic acid system.The reaction mechanisms in connection with the nature of CAN in various solvent systems are discussed.
- Torii, Sigeru,Tanaka, Hideo,Inokuchi, Tsutomu,Nakane, Shoji,Akada, Mitsuo,et al.
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p. 1647 - 1652
(2007/10/02)
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- Metalation of o-Halostyrene Oxides. Preparation of Benzocyclobutenols
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o-Bromo- and o-iodostyrene oxides are converted in fair to good yield to benzocyclobutenols upon treatment with n-BuLi and MgBr2 in THF or ether at -78 deg C, followed by warming to room temperature.The reaction involves initial halogen-lithium exchange followed either by MgBr2-initiated opening of the epoxide function to a haloalkoxide or rearrangement of the epoxide function to a ketone or aldehyde followed by cyclization.Benzocyclobutenol formation was not successful in the case of o-halostilbene oxides.
- Akguen, Eyup,Glinski, Margaret B.,Dhawan, Kasturi L.,Durst, Tony
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p. 2730 - 2734
(2007/10/02)
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- Preparation of Benzocyclobutenols from o-Halostyrene Oxides
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Reaction of several o-bromo- and o-iodostyrene oxides, dissolved in THF at -78 deg C containing a suspension of MgBr2, with n-BuLi gave benzocyclobutenols in 50-83 percent yield.
- Dhawan, Kasturi L.,Gowland, Barbara D.,Durst, Tony
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p. 922 - 924
(2007/10/02)
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