- Synthesis method of montelukast sodium intermediate
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The invention is applicable to the technical field of medicine synthesis, and provides a synthesis method of a montelukast sodium intermediate. The method comprises the following steps of: generatinga compound II from halogenated benzene under the action
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Paragraph 0067; 0068
(2021/03/03)
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- Exploring boron applications in modern agriculture: A structure-activity relationship study of a novel series of multi-substitution benzoxaboroles for identification of potential fungicides
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Several boron-containing small molecules have been approved by the US FDA to treat human diseases. We explored potential applications of boron-containing compounds in modern agriculture by pursuing multiple research and development programs. Here, we report a novel series of multi-substitution benzoxaboroles (1–36), a compound class that we recently reported as targeting geranylgeranyl transferase I (GGTase I) and thereby inhibiting protein prenylation (Kim et al., 2020). These compounds were designed, synthesized, and tested against the agriculturally important fungal pathogens Mycosphaerella fijiensis and Colletotrichum sublineolum in a structure–activity relationship (SAR) study. Compounds 13, 28, 30, 34 and 36 were identified as active leads with excellent antifungal MIC95 values in the range of 1.56–3.13 ppm against M. fijiensis and 0.78–3.13 ppm against C. sublineolum.
- Liu, Chunliang,Steere, Luke,McGregor, Cari,Frederick, Brittany H.,Pastoor, Timothy,Zhou, Yasheen,Liu, C. Tony,Cai, Yan,Zhou, Haibo,Xu, Musheng,Wang, Jiangong,Kim, Sang Hu,Whitesell, Luke,Cowen, Leah E.,Zhang, Yong-Kang
-
supporting information
(2021/05/19)
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- BORON CONTAINING COMPOUNDS AND THEIR USES
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The present disclosure contemplates novel boron-containing compounds and their uses as active agents that exhibit pesticidal activity such as antimicrobial, insecticidal, arachnicidal, and/or anti parasitic activity. An agrochemical composition containing such a compound and its use in, animal health, agriculture, or horticulture is also contemplated. A method for promoting plant performance and/or controlling, reducing, preventing, ameliorating, or inhibiting microbes, insects, arachnids, and/or parasites on or in an animal, a plant, a plant part, plant propagation material, and/or harvested fruits or vegetables is also contemplated.
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Paragraph 0224-0225
(2020/03/29)
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- Benzoxaborole Catalyst for Site-Selective Modification of Polyols
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The site-selective modification of polyols bearing several hydroxyl groups without the use of protecting groups remains a significant challenge in synthetic chemistry. To address this problem, novel benzoxaborole derivatives were designed as efficient catalysts for the highly site-selective and protecting-group-free modification of polyols. To identify the effective substituent groups enhancing the catalytic activity and selectivity, a series of benzoxaborole catalysts 1a–k were synthesized. In-depth analysis for the substituent effect revealed that 1i–k, bearing multiple electron-withdrawing fluoro- and trifluoromethyl groups, exhibited the greatest catalytic activity and selectivity. Moreover, 1i-catalyzed benzoylation, tosylation, benzylation, and glycosylation of various cis-1,2-diol derivatives proceeded with good yield and site-selective manner.
- Kusano, Shuhei,Miyamoto, Shoto,Matsuoka, Aki,Yamada, Yuji,Ishikawa, Ryuta,Hayashida, Osamu
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supporting information
p. 1598 - 1602
(2020/02/11)
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- Rh-Catalyzed Asymmetric Hydrogenation of α,β- and β,β-Disubstituted Unsaturated Boronate Esters
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A highly enantioselective hydrogenation of α,β-unsaturated boronate esters catalyzed by Rh-(S)-DTBM-Segphos complex has been developed. Both (Z)-α,β- and β,β-disubstituted substrates can be successfully hydrogenated to afford chiral boronates with excellent enantioselectivities, up to 98 % ee. Furthermore, the obtained chiral boronate esters, as important versatile synthetic intermediates are successfully transformed to the corresponding chiral alcohols, amines and other important derivatives with maintained enantioselectivities.
- Hou, Guohua,Shen, Xin,Yan, Qiaozhi,Zi, Guofu
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- Spatial anion control on palladium for mild C-H arylation of arenes
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C-H arylation of arenes without the use of directing groups is a challenge, even for simple molecules, such as benzene. We describe spatial anion control as a concept for the design of catalytic sites for C-H bond activation, thereby enabling nondirected C-H arylation of arenes at ambient temperature. The mild conditions enable late-stage structural diversification of biologically relevant small molecules, and site-selectivity complementary to that obtained with other methods of arene functionalization can be achieved. These results reveal the potential of spatial anion control in transition-metal catalysis for the functionalization of C-H bonds under mild conditions.
- Dhankhar, Jyoti,González-Fernández, Elisa,Dong, Chao-Chen,Mukhopadhyay, Tufan K.,Linden, Anthony,?ori?, Ilija
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supporting information
p. 19040 - 19046
(2020/11/13)
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- Unexpected reactivity of cyclic perfluorinated iodanes with electrophiles
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We have found that cyclic perfluorinated iodanes react with electrophiles (E+ = Br, Cl, F, I) to afford perfluorinated E-RF compounds. This reactivity is unexpected since cyclic perfluorinated iodanes are considered as electrophilic reagents that normally react with nucleophiles (e.g. Nu- = SR, OR) to afford Nu-RF products. The utility of this new transformation is demonstrated for a [18F]CF3CF2-containing compound which was prepared from [18F]XeF2 obtained from cyclotron produced [18F]fluoride.
- Gruber, Stefan,Ametamey, Simon M.,Schibli, Roger
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supporting information
p. 8999 - 9002
(2018/08/21)
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- SILICON-BASED CROSS COUPLING AGENTS AND METHODS OF THEIR USE
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Compositions and methods using silicon-based cross-coupling agents in the formation of carbon-carbon and carbon-nitrogen bonds are described.
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Paragraph 0087
(2016/02/10)
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- Compounds of the menthane series. Synthesis of unsaturated primary alcohols with the o- and p-menthane skeletons
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Precursors to terpene alcohols of the o- and p-menthane series (o-cimen-7-ol and o- and p-cimen-9-ols) were synthesized, and their reduction with lithium in ethylenediamine was studied. The reduction of o- and p-cimen-9-ols in the presence of isopropyl alcohol selectively afforded the corresponding 1,4-dihydro derivatives. Under analogous conditions, o-cimen-7-ol was converted into a mixture of unsaturated hydrocarbons. The reduction with lithium in ethylenediamine in the absence of isopropyl alcohol in all cases gave mixtures of menthene alcohols.
- Fedorov,Fedorova,Sheverdov,Pavlov,Eremkin
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p. 806 - 812
(2016/07/30)
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- Synthesis of Mavatrep: A Potent Antagonist of Transient Receptor Potential Vanilloid-1
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The process development of Mavatrep (1), a potent transient receptor potential vanilloid-1 (TRPV1) antagonist, is described. The two key synthetic transformations are the synthesis of (E)-6-bromo-2-(4-(trifluoromethyl)styryl)1H-benzo[d]imidazole (4) and the Suzuki coupling of 4 with 3,3-dimethyl-3H-benzo[c][1,2]oxaborol-1-ol (5). Compound 1a was prepared in four chemical steps in 63% overall yield.
- Wells, Kenneth M.,Mehrman, Steven J.,Abdel-Magid, Ahmed F.,Ferraro, Caterina,Scott, Lorraine,Zhong, Hua Marlon,Teleha, Christopher A.,Ballentine, Scott,Li, Xun,Russell, Ronald K.,Spink, Jan M.,Diamond, Craig,Youells, Scott,Zhang, Yongzheng,Tsay, Fuh-Rong,Cesco-Cancia, Sergio,Manzo, Stephen M.,Beauchamp, Derek A.
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p. 1774 - 1783
(2015/12/01)
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- An enantioselective formal synthesis of montelukast sodium
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A formal synthesis of the antiasthma drug montelukast sodium is described, wherein the key chiral diol intermediate was accessed with greater convergence of the C-C bond-forming steps as compared to previous routes. Improved synthetic efficiency was achie
- Bollikonda, Satyanarayana,Mohanarangam, Saravanan,Jinna, Rajender Reddy,Kandirelli, Venkata Kiran Kumar,Makthala, Laxman,Sen, Saikat,Chaplin, David A.,Lloyd, Richard C.,Mahoney, Thomas,Dahanukar, Vilas Hareshwar,Oruganti, Srinivas,Fox, Martin E.
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p. 3891 - 3901
(2015/06/02)
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- Benzo[d]imidazole transient receptor potential vanilloid 1 antagonists for the treatment of pain: Discovery of trans-2-(2-{2-[2-(4-Trifluoromethyl-phenyl)-vinyl]-1H-benzimidazol-5-yl}-phenyl)-propan-2-ol (Mavatrep)
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Reported herein is the design, synthesis, and pharmacologic characterization of a class of TRPV1 antagonists constructed on a benzo[d]imidazole platform that evolved from a biaryl amide lead. This design composes three sections: a 2-substituted 5-phenyl headgroup attached to the benzo[d]imidazole platform, which is tethered at the two position to a phenyl tail group. Optimization of this design led to the identification of 4 (mavatrep), comprising a trifluoromethyl-phenyl-vinyl tail. In a TRPV1 functional assay, using cells expressing recombinant human TRPV1 channels, 4 antagonized capsaicin-induced Ca2+ influx, with an IC50 value of 4.6 nM. In the complete Freund's adjuvant- and carrageenan-induced thermal hypersensitivity models, 4 exhibited full efficacy, with ED80 values of 7.8 and 0.5 mg/kg, respectively, corresponding to plasma levels of 270.8 and 9.2 ng/mL, respectively. On the basis of its superior pharmacologic and safety profile, 4 (mavatrep) was selected for clinical development for the treatment of pain.
- Parsons, William H.,Calvo, Raul R.,Cheung, Wing,Lee, Yu-Kai,Patel, Sharmila,Liu, Jian,Youngman, Mark A.,Dax, Scott L.,Stone, Dennis,Qin, Ning,Hutchinson, Tasha,Lubin, Mary Lou,Zhang, Sui-Po,Finley, Michael,Liu, Yi,Brandt, Michael R.,Flores, Christopher M.,Player, Mark R.
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p. 3859 - 3874
(2015/05/27)
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- Structure-reactivity relationship of trifluoromethanesulfenates: Discovery of an electrophilic trifluoromethylthiolating reagent
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A family of electrophilic trifluoromethanesulfenates was prepared. Structure-reactivity relationship studies showed that the substituted groups on the aryl ring of the trifluoromethylthiolating reagent did not have an obvious influence on their reactivities. A simplified electrophilic trifluoromethylthiolating reagent 1c was then identified that can react with a wide range of nucleophiles such as Grignard reagents, arylboronic acids, alkynes, indoles, β-ketoesters, oxindoles, and sodium sulfinates under mild reaction conditions. A variety of functional groups were tolerated under these conditions.
- Shao, Xinxin,Xu, Chunfa,Lu, Long,Shen, Qilong
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p. 3012 - 3021
(2015/03/30)
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- Synthesis of Multisubstituted Triphenylenes and Phenanthrenes by Cascade Reaction of o-Iodobiphenyls or (Z)-β-Halostyrenes with o-Bromobenzyl Alcohols through Two Sequential C-C Bond Formations Catalyzed by a Palladium Complex
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o-Bromobenzyl alcohol has been developed as a novel annulating reagent, bearing both nucleophilic and electrophilic substituents, for the facile synthesis of polycyclic aromatic hydrocarbons. A palladium/electron-deficient phosphine catalyst efficiently coupled o-iodobiphenyls or (Z)-β-halostyrenes with o-bromobenzyl alcohols to afford triphenylenes and phenanthrenes, respectively. The present cascade reaction proceeded through deacetonative cross-coupling and sequential intramolecular cyclization. An array of experimental data suggest that the reaction mechanism involves the equilibrium of 1,4-palladium migration.
- Iwasaki, Masayuki,Araki, Yasuhiro,Iino, Shohei,Nishihara, Yasushi
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p. 9247 - 9263
(2015/09/28)
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- PREPARATION OF PRECURSORS FOR LEUKOTRIENE ANTAGONISTS
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The present invention relates to an improved process for the preparation of a compound having formula (I). The compound having formula (I) is the backbone diol precursor/intermediate used to produce montelukast sodium. Montelukast sodium is a leukotriene
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Page/Page column 20; 21
(2014/06/11)
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- Synthesis of dihydroisobenzofurans via palladium-catalyzed sequential alkynylation/annulation of 2-bromobenzyl and 2-chlorobenzyl alcohols under microwave irradiation
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The palladium-catalyzed synthesis of dihydroisobenzofurans has been performed by sequential Sonogashira cross-coupling/cyclization reactions between terminal alkynes and 2-(hydroxymethyl)bromoand chlorobenzenes in methanol as solvent at 130 °C under microwave irradiation. A 4,4'-dichlorobenzophenone oxime-derived chloro-bridged palladacycle is an efficient pre-catalyst to perform this tandem process using 2-dicyclohexylphosphanyl-2',4',6'-triisopropylbiphenyl (Xphos) as ancillary ligand and potassium hydroxide as base in the absence of a copper cocatalyst. Under these conditions, functionalized 2-bromo- and 2-chlorobenzaldehydes are also suitable partners in the domino process affording phthalans in good yields. All the reactions can be performed under air and employing reagentgrade chemicals under low loading conditions (1 mol% Pd).
- Buxaderas, Eduardo,Alonso, Diego A.,Njera, Carmen
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supporting information
p. 3415 - 3421
(2015/01/09)
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- The design, synthesis and validation of recoverable and readily reusable siloxane transfer agents for Pd-catalyzed cross-coupling reactions
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The development of competent, recoverable and reusable 1-oxa-2- silacyclopentene (siloxane) transfer agents for Pd-catalyzed cross-coupling reactions (CCRs) of organolithium reagents with aryl and alkenyl iodides has been achieved. Drawbacks of the first-generation siloxane-transfer agent (1), relating to facile recovery for potential recycling, have been addressed.
- Martinez-Solorio, Dionicio,Hoye, Adam T.,Nguyen, Minh H.,Smith, Amos B.
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supporting information
p. 2454 - 2457
(2013/07/05)
-
- SILICON-BASED CROSS COUPLING AGENTS AND METHODS OF THEIR USE
-
Compositions and methods using silicon-based cross-coupling agents in the formation of carbon-carbon and carbon-nitrogen bonds are described.
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Page/Page column 40
(2014/01/08)
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- Palladium-catalyzed annulation of o-iodobiphenyls with o-bromobenzyl alcohols: Synthesis of functionalized triphenylenes via C-C and C-H bond cleavages
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Treatment of o-iodobiphenyls with o-bromobenzyl alcohols in the presence of cesium carbonate under palladium catalysis affords a series of highly substituted triphenylenes. The reaction involves two C-C bond formations and C-C and C-H bond cleavages. A combination of palladium and an electron-deficient phosphine ligand proves to be effective for both decarbonylative cross-coupling and intramolecular cyclization.
- Iwasaki, Masayuki,Iino, Shohei,Nishihara, Yasushi
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supporting information
p. 5326 - 5329
(2013/11/06)
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- BORON CONTAINING POLYBASIC BACTERIAL EFFLUX PUMP INHIBITORS AND THERAPEUTICS USES THEREOF
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Disclosed herein are polybasic bacterial efflux pump inhibitors containing boronic acid functionality and theft methods of synthesis, methods of use, and pharmaceutical compositions. Some embodiments include methods of treating or preventing a bacterial infection by co-administering to a subject infected with bacteria or at risk of infection with bacteria the efflux pump inhibitor with another anti-bacterial agent
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Page/Page column 62
(2012/08/28)
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- A domino palladium-catalyzed C-C and C-O bonds formation via dual O-H bond activation: Synthesis of 6,6-dialkyl-6 H -benzo[ c ]chromenes
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An efficient Pd-catalyzed domino reaction of α,α-dialkyl-(2- bromoaryl)methanols to 6,6-dialkyl-6H-benzo[c]chromenes is presented. Their formation can be explained via a five membered Pd(II)-cycle that efficiently involves a domino homocoupling with the second molecule, β-carbon cleavage, and finally intramolecular Buchwald-Hartwig cyclization. This domino process effectively involves breaking of five σ-bonds (2C-Br, 2O-H, and a C-C) and formation of two new σ-bonds (C-C and C-O). This mechanistic pathway is unprecedented and further illustrates the power of transition metal catalysis.
- Mahendar, Lodi,Krishna, Jonnada,Gopi Krishna Reddy, Alavala,Venkat Ramulu, Bokka,Satyanarayana, Gedu
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p. 628 - 631
(2012/03/11)
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- BORON-CONTAINING SMALL MOLECULES AS ANTIPROTOZOAL AGENTS
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This invention provides, among other things, novel compounds useful for treating protozoal infections, pharmaceutical compositions containing such compounds, as well as combinations of these compounds with at least one additional therapeutically effective
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Page/Page column 137-138
(2011/02/24)
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- Synthesis and SAR of acyclic HCV NS3 protease inhibitors with novel P4-benzoxaborole moieties
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We have synthesized and evaluated a new series of acyclic P4-benzoxaborole-based HCV NS3 protease inhibitors. Structure-activity relationships were investigated, leading to the identification of compounds 5g and 17 with low nanomolar potency in the enzymatic and cell-based replicon assay. The linker-truncated compound 5j was found to exhibit improved absorption and oral bioavailability in rats, suggesting that further reduction of molecular weight and polar surface area could result in improved drug-like properties of this novel series.
- Li, Xianfeng,Zhang, Suoming,Zhang, Yong-Kang,Liu, Yang,Ding, Charles Z.,Zhou, Yasheen,Plattner, Jacob J.,Baker, Stephen J.,Bu, Wei,Liu, Liang,Kazmierski, Wieslaw M.,Duan, Maosheng,Grimes, Richard M.,Wright, Lois L.,Smith, Gary K.,Jarvest, Richard L.,Ji, Jing-Jing,Cooper, Joel P.,Tallant, Matthew D.,Crosby, Renae M.,Creech, Katrina,Ni, Zhi-Jie,Zou, Wuxin,Wright, Jon
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supporting information; experimental part
p. 2048 - 2054
(2011/04/24)
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- Lipase-mediated resolution of substituted 2-aryl-propanols: Application to the enantioselective synthesis of phenolic sesquiterpenes
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A comprehensive study of the lipase-mediated resolution of substituted 2-aryl-propanols is reported. The latter alcohols were submitted to the irreversible acetylation catalyzed either by PPL, CRL, or lipase PS. The enantioselectivity of these transformations was dependent on the type of lipase used. The type of substituents and particularly their position on the aromatic ring strongly affected the selectivity of the reaction. The experiments described prove that PPL is the more versatile lipase catalyzing the acetylation with an enantiomeric ratio (E) value that ranges from 1 up to 144, depending on the substrate used. Conversely, the same transformations were catalyzed by CRL and lipase PS with an enantiomeric ratio value, which is always less than 5. The remarkable behavior of PPL was exploited in the large scale resolution of some substituted 2-aryl-propanols whose enantiomeric forms are relevant building blocks in the enantioselective synthesis of phenolic sesquiterpenes. By these means, the synthesis of (S)-turmeronol B and the formal syntheses of (R)-curcumene, (R)-curcuphenol, (R)-xanthorrhizol, and (R)-curcuhydroquinone were accomplished.
- Serra, Stefano
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experimental part
p. 619 - 628
(2011/07/08)
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- Synthesis and spin trapping properties of 1,1-dimethyl-3-(trifluoromethyl)- 1H-isoindole N-oxide
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We have achieved an efficient synthesis of 1,1-dimethyl-3-(trifluoromethyl) -1H-isoindole N-oxide (2) in 39% yield by seven steps from 2-bromobenzoic acid (3). This compound serves as a spin trap reagent, giving a strong and stable ESR signal of the radic
- Hatano, Bunpei,Miyoshi, Katsunori,Sato, Haruna,Ito, Tomohiro,Ogata, Tateaki,Kijima, Tatsuro
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supporting information; experimental part
p. 5399 - 5401
(2010/11/02)
-
- ortho-Effect on the acid-catalyzed hydration of 2-substituted α-methylstyrenes
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α-Methylstyrene and nine ortho-substituted analogs have been synthesized and the kinetics of their acid-catalyzed hydration in aqueous solutions of sulfuric acid at 25°C have been investigated. The kinetic acidity function HS has been constructed from the dependence of the observed rate constants kobs on the sulfuric acid concentration. The catalytic rate constants of the acid-catalyzed hydration kortho have been calculated as well. The identical shape of the kinetic acidity functions for ortho- and para-derivatives confirms what the consistent mechanism A-SE2 of the acid-catalyzed hydration has already proved for the corresponding paraderivatives. The A-SE2 mechanism involves a rate-determining proton transfer of the hydrated proton to the substrate. From the dependence of the catalytic rate constants of the ortho-derivatives on the catalytic rate constants of the para-derivatives, it is seen that the logarithm of the catalytic rate constant for hydrogen as a substituent is markedly out of the range of the other substituents and, simultaneously, that the ortho-derivatives react significantly slower than the corresponding para-derivatives. In correlation with the substitent constants σp+, a reaction constant of ρ+= -1.45 have been found. The constant is, in absolute value, considerably smaller than that for para-derivatives (ρ+ = -3.07). In parallel, the steric effects are enforced more significantly for the monoatomic substituents (slope of the Charton's constants 3.92) than for substituents including more atoms (slope of the Charton's constants 2.09). A small value of the reaction constant ρ+ has been elucidated due to the lower conjugation between the reaction centre and the benzene ring as a consequence of the geometric twist of the reaction centre out of the main aromatic plane accompanied by fading mesomeric interaction between the reaction centre and the substituents attached to the benzene ring. The isopropyl group in the carbocation is twisted less out of the aromatic plane for the monoatomic substituents and, therefore, also a small difference in the bulk of substituents has considerable steric influence on the conjugation between the carbocation and the benzene ring bearing substituents. On the contrary, the isopropyl group in the carbocations with polyatomic substituents is twisted to such a degree that changes in the bulk of substituents affect the resonant stabilization negligibly. Similar conclusions were also deduced from the correlations of the substitution constants σI and σR+.
- Prusek, Ondrej,Bures, Filip,Pytela, Oldrich
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experimental part
p. 85 - 99
(2009/06/06)
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- Benzimidazole Modulators of VR1
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The invention is directed to compounds of Formula (I): to pharmaceutical compositions containing such compounds and to methods of treatment using them.
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Page/Page column 171-172
(2008/06/13)
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- CYCLOALKANOPYRIDINE DERIVATIVE
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Provided are cycloalkanopyridine derivatives of formula [I]: [wherein the symbols are the same as those stated in the description]. The compounds act as a nociceptin receptor antagonist, and are useful as medicines for diseases associated with a nociceptin receptor, for example, as a reliever against tolerance to a narcotic analgesic; a reliever against dependence on or addiction to a narcotic analgesic; an analgesic enhancer; an antiobesitic or appetite suppressor; a treating or prophylactic agent for cognitive impairment and dementia/amnesia; an agent for treating developmental cognitive abnormality; a remedy for schizophrenia; an agent for treating neurodegenerative diseases; an anti-depressant or treating agent for affective disorder; a treating or prophylactic agent for diabetes insipidus; a treating or prophylactic agent for polyuria; or a remedy for hypotension.
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Page/Page column 58
(2010/11/24)
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- ALPHA ARYL OR HETEROARYL METHYL BETA PIPERIDINO PROPANAMIDE COMPOUNDS AS ORL1-RECEPTOR ANTAGONIST
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This invention provides the compounds of formula (I): or a pharmaceutically acceptable ester of such compound, or a pharmaceutically acceptable salt thereof, wherein Ri and R2 independently represent a hydrogen atom or the like; R3 represents a hydrogen atom, or the like; R4 represents a hydrogen atom or the like; (formula II) represents one of the following or the like; R5 represents an aryl group having from 6 to 10 ring atoms or the like; X represents an oxygen atom, or the like; Y represents an oxgen atom or the like and n represents an integer 0, 1 or 2. These compounds have ORL1-receptor antagonist activity; and therefore, are useful to treat diseases or conditions such as pain, various CNS diseases etc.
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Page/Page column 141
(2010/02/14)
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- Effect of benzylic methyl groups on kinetic basicity of amine ligand in o-boron substituted N,N-dimethylbenzylamines
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Rates of the dissociation of the intramolecular B-N coordination bond in two series of phenylborane derivatives, the boronate and diethylborane complexes, with -CHMeNMe2 or -CMe2NMe2 group at the o-position were determined
- Toyota, Shinji,Asakura, Mitsuhiro,Futawaka, Tadahiro,Oki, Michinori
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p. 1879 - 1885
(2007/10/03)
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- INTRAMOLECULAR CYCLIZATION OF 2'-OLEFINIC SIDE-CHAINS ON ANODICALLY OXIDIZED 4-PHENYLPHENOLS. THE EFFECT OF OLEFIN SUBSTITUENTS ON CARBON-CARBON BOND FORMATION
-
The anodic oxidation of 4-(2'-alkenylphenyl)phenols in acetonitrile/methanol affords spirodienones arising from cyclization of the olefinic side-chain to the 4-position of the phenol and reaction of the resulting benzylic cation with methanol.The efficiency of this carbon-carbon bond-forming reaction is dependent upon the olefinic substituents.
- Morrow, Gary W.,Chen, Ying,Swenton, John S.
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p. 655 - 664
(2007/10/02)
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- Substituted 1,3-dihydrospiro(isobenzofuran)s
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Novel substituted 1,3-dihydrospiro[isobenzofuran]s and methods of preparing the same are described. These compounds are useful as antidepressants, tranquilizers, analgetic agents and intermediates therefor.
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