cas 7507-86-0, 2-Bromo-5-methoxybenzaldehyde

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Elaboration of the isochromane system of stephaoxocanes employing an Oxa-Pictet Spengler type cyclization
An approach to the synthesis of the isochromane moiety embodying the AC-ring system of the stephaoxocanes, by the use of an Oxa-Pictet Spengler type cyclization strategy, is reported.
Kaufman, Teodoro S.,Bernardi, Carmem R.,Cipulli, Marcos,Silveira, Claudio C.
p. 493 - 494
(2000)
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Catalytic Cyclotrimerization Pathway for Synthesis of Selaginpulvilins C and D: Scope and Limitations
A facile and unified approach to the main selaginpulvilin's framework was achieved by catalytic [2 + 2 + 2]-cyclotrimerization of a triyne with monosubtituted alkynes. The reaction proceeded with high "ortho"selectivity by using Wilkinson's catalyst (RhCl
Rycek, Lukas,Mateus, Miguel,Beytlerová, Nela,Kotora, Martin
p. 4511 - 4515
(2021/04/12)

COMPOUNDS AND COMPOSITIONS FOR USE IN TREATING SKIN DISORDERS
Provided herein is a compound of formula (XXXII) or a pharmaceutically acceptable salt, solvate, hydrate, stereoisomer thereof or a physiologically functional derivative thereof, wherein R1, R2, R3, G, A, E, n, p, and q are defined herein. Also provided herein are compositions comprising a compound of formula (XXXII), and methods of using a compound of formula (XXXII), e.g., in the treatment or prevention of skin disorders.
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Paragraph 0592; 0620-0622

(2021/08/06)

A transition metal free expedient approach for the C[dbnd]C bond cleavage of arylidene Meldrum's acid and malononitrile derivatives
A transition metal free expedient approach for the C[dbnd]C bond cleavage of electron deficient alkenes such as arylidene Meldrum's acid and malononitrile derivatives are discussed. The C[dbnd]C bond of these compound were cleaved to benzoic acid in good yield at high temperature. Most importantly, with oxone in CH3CN/H2O at 45 °C or m-CPBA in DCM or NaClO2 in THF/H2O or PIDA in THF at room temperature furnished benzaldehyde derivatives selectively in excellent yields.
Suresh, Muthiah,Kumari, Anusueya,Singh, Raj Bahadur
(2019/09/10)

Atroposelective Total Synthesis of the Fourfold ortho-Substituted Naphthyltetrahydroisoquinoline Biaryl O,N-Dimethylhamatine
A stereoselective total synthesis of O,N-dimethylhamatine, an analogue of an axially chiral naphthylisoquinoline natural biaryl product from tropical Ancistrocladus lianas, is reported. The route features a late-stage atropo-diastereoselective biaryl bond
Slack, Eric D.,Seupel, Raina,Aue, Donald H.,Bringmann, Gerhard,Lipshutz, Bruce H.
supporting information
p. 14237 - 14245
(2019/11/11)

A novel donor-π-acceptor anthracene monomer: Towards faster and milder reversible dimerization
A novel functional 2,6-substituted donor-acceptor anthracene derivative, bearing a long alkyl spacer and a polymerizable end-group, is synthesized from readily available compounds. This monomer possesses conjugated electron donor and acceptor moieties to achieve UV absorption and anthracene dimerization at higher wavelengths and under milder conditions, than anthracene and other reported anthracene derivatives. The compound was shown to absorb at higher wavelengths and dimerize much faster compared to most 9-substituted anthracenes. The fast photochemical and relatively slow thermal scission of the dimers were studied and related to the chemical structure, i.e. the 2,6-substitution.
Van Damme, Jonas,van den Berg, Otto,Brancart, Joost,Van Assche, Guy,Du Prez, Filip
p. 912 - 920
(2019/01/16)

Palladium-catalyzed ortho-C(sp2)[sbnd]H bromination of benzaldehydes via a monodentate transient directing group strategy
A facile and efficient monodentate transient directing group strategy was developed to enable the palladium-catalyzed ortho-C(sp2)[sbnd]H bromination of benzaldehydes. A broad scope of benzaldehydes were transformed into the desired products by employing 2-amino-5-chlorobenzotrifluoride as a monodentate transient directing group, demonstrating good functional group tolerance. Mild reaction conditions and no requirement for a silver salt are also features of this strategy.
Yong, Qiyun,Sun, Bing,Zhang, Fang-Lin
supporting information

(2019/11/03)

Heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis
A general and efficient method for heterocyclization involving benzylic C(sp3)-H functionalization enabled by visible light photoredox catalysis to access a wide range of structurally diverse oxygen as well as nitrogen heterocycles up to a gram scale is reported. The potential application of this new methodology is demonstrated by the total synthesis of (-)-codonopsinine and (+)-centrolobine. Herein it is proposed that selectfluor, unlike a fluorinating reagent, acts as an oxidative quencher and a hydrogen radical acceptor.
Pandey, Ganesh,Laha, Ramkrishna,Mondal, Pradip Kumar
supporting information
p. 9689 - 9692
(2019/08/15)

Rh(III)-Catalyzed Phosphine Oxide Migration Reactions: Selective Synthesis of 3-Phosphinoylindoles
3-Phosphinoylindoles are important components of biological active natural products and materials in pharmaceuticals. Herein, a new approach for the synthesis of 3-phosphinoylindoles has been established by a Rh(III)-catalyzed cyclization from readily acc
Wang, Chun-Hai,Yang, Shang-Dong
p. 2401 - 2404
(2018/09/10)

The First Kilogram Synthesis of Beclabuvir, an HCV NS5B Polymerase Inhibitor
The process development and kilogram-scale synthesis of beclabuvir (BMS-791325, 1) is described. The convergent synthesis features the use of asymmetric catalysis to generate a chiral cyclopropane fragment and coupling with an indole fragment via an alkyl
Bien, Jeffrey,Davulcu, Akin,Delmonte, Albert J.,Fraunhoffer, Kenneth J.,Gao, Zhinong,Hang, Chao,Hsiao, Yi,Hu, Wenhao,Katipally, Kishta,Littke, Adam,Pedro, Aghogho,Qiu, Yuping,Sandoval, Maria,Schild, Richard,Soltani, Michelle,Tedesco, Anthony,Vanyo, Dale,Vemishetti, Purushotham,Waltermire, Robert E.
p. 1393 - 1408
(2018/09/06)

A gold catalytic oxidation of benzyl alcohol synthesis method (by machine translation)
The present invention provides a kind of organic synthesis in the oxidation of benzyl alcohol synthesis method, the reaction formula is as follows, in the formula 1 containing different substituents is benzyl alcohol, in the formula 2 is triphenylcarbinol compound. The required reaction of gold catalyst is Ph3 PAuCl, Ph3 PAuNTf2 , HAuCl4 , NaAuCl4 , Ph3 PAuOTf, Ph3 PAuSbF6 , IPrAuCl, gold. The required reaction medium is: solvent-free, toluene, are three-toluene, 1, 2 - dichloroethane, tetrahydrofuran, acetonitrile, acetone. The reaction implementing microwave heating of reactor, the method of the invention the oxidizing agent triphenylcarbinol for commercial products, cheap, and simple experimental operation, substrate and wide range of application. (by machine translation)
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Paragraph 0034-0037; 0041; 0055-0057; 0059-0061

(2017/08/25)

Tandem Pd-catalyzed C-C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes
The first successful synthesis of 1H-2,3-benzoxazine 3-oxides has been described. The efficiency of the approach is provided by the C-C-coupling of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitroalkanes catalyzed by Pd(dba)2/JohnPhos system followed by in situ recyclization of the intermediates. Several representative transformations allowing selective modification of the nitronate as well as malonate functionalities in the resulting compounds are demonstrated.
Mikhaylov, Andrey A.,Dilman, Alexander D.,Novikov, Roman A.,Khoroshutina, Yulia A.,Struchkova, Marina I.,Arkhipov, Dmitry E.,Nelyubina, Yulia V.,Tabolin, Andrey A.,Ioffe, Sema L.
supporting information
p. 11 - 14
(2015/12/23)

Water-soluble isoindolo[2,1-a]quinoxalin-6-imines: In vitro antiproliferative activity and molecular mechanism(s) of action
Water-soluble isoindoloquinoxalin (IIQ) imines and the corresponding acetates were conveniently prepared from the key intermediates 2-(2′-aminophenyl)-2H-isoindole-1-carbonitriles obtained by a Strecker reaction between substituted 1,2-dicarbaldehydes and 1,2-phenylenediamines. Both series were screened by the National Cancer Institute (Bethesda, MD) and showed potent antiproliferative activity against a panel of 60 human tumor cell lines. Several of the novel compounds showed GI50 values at a nanomolar level on the majority of the tested cell lines. Among IIQ derivatives, methoxy substituents at positions 3 and 8 or/and 9 were especially effective in impairing cell cycle progression and inducing apoptosis in cancer cells. These effects were associated to IIQ-mediated impairment of tubulin polymerization at pharmacologically significant concentrations of tested compounds. In addition, impaired DNA topoisomerase I functions and perturbation in telomere architecture were observed in cells exposed to micromolar concentrations of IIQ derivatives. The above results suggest that IIQ derivatives exhibit multi-target cytotoxic activities.
Parrino, Barbara,Carbone, Anna,Ciancimino, Cristina,Spanò, Virginia,Montalbano, Alessandra,Barraja, Paola,Cirrincione, Girolamo,Diana, Patrizia,Sissi, Claudia,Palumbo, Manlio,Pinato, Odra,Pennati, Marzia,Beretta, Giovanni,Folini, Marco,Matyus, Peter,Balogh, Balázs,Zaffaroni, Nadia
p. 149 - 162
(2015/03/18)

Fe(III)-catalyzed trityl benzyl ether formation and disproportionation cascade reactions to yield benzaldehydes
During investigating water-compatible Lewis acids catalyzed etherifications using alcohols as alkylating reagents directly, we developed Fe(III)-catalyzed trityl benzyl ether formations irradiated by microwave. Then an in situ trityl benzyl ether formation and disproportionation cascade reaction was achieved to yield the benzaldehyde products with good functional group tolerances under neat conditions at relative higher temperatures. The substituent effects of the substrates on the etherification and disproportionation were explored by changing the substitutions on benzyl alcohols and triarylmethanols using chemical kinetic plots methods and the mechanism of the transformation was studied by crossover experiments. The etherification and disproportionation cascade process could be conveniently scaled up in laboratory without losing much efficiency.
Wang, Xiaoyu,Du, Chuan,Shi, Hui,Pang, Yadong,Jin, Shengfei,Hou, Yuqian,Wang, Yanshi,Peng, Xiaoshi,Xiao, Jianyong,Liu, Yang,Liu, Yongxiang,Cheng, Maosheng
p. 6744 - 6748
(2015/08/24)

Process for preparing 8-hydroxyclomipramine or its pharmaceutically acceptable salt
Provided are a method for synthesizing a novel intermediate, namely, 3-(3-chloro-8-methoxy-10,11-dehydro-5H-dibenzo[b,f]Azepine-5-yl)-N,N-dimethylpropan-1-amine or 8-hydroxyclomipramine using a salt thereof, or a pharmaceutically acceptable salt thereof,
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Paragraph 0063-0065

(2016/10/10)

Synthesis and antimicrobial activity of azepine and thiepine derivatives
A series of new pyridobenzazepine and pyridobenzothiepine derivatives was synthesized by Pd-catalyzed formation of C-N and C-S bonds. All synthesized compounds were tested for their in vitro antimicrobial activity. The pyridobenzazepine derivatives showed better antibacterial and antifungal activity than the corresponding dipyridoazepine analogue. Among the synthesized azepines, derivative 8 displayed potent activity against the tested bacteria (MIC ranged 39-78 μg mL-1), while azepine 12 showed promising antifungal activity (MIC ranged 156-313 μg mL-1). The synthesized thiepine derivatives exhibited weak antibacterial activity, but showed pronounced antifungal activity.
Boinovi, Nina,Novakovi, Irena,Rajai, Sladana Kosti,Opsenica, Igor M.,olaja, Bogdan A.
p. 839 - 852
(2015/08/24)

Bromination of arenes using I2O5-KBr in water
An efficient and environmentally benign bromination of various aromatic compounds using aN aqueous I2O5-KBr system at room temperature has been developed in this work. A series of aromatic compounds such as acetophenones, benzaldehydes, benzoic acids, anilines, amides, and aminopyridine have been successfully brominated in excellent regioselectivities and good yields under the typical reaction conditions. The features of KBr as brominating reagent, water as solvent, and mild conditions make this system an attractive synthetic procedure. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]
Hou, Jieping,Li, Zejiang,Jia, Xiao-Dong,Liu, Zhong-Quan
supporting information
p. 181 - 187
(2013/12/04)

Simple, copper(I)-catalyzed oxidation of benzylic/allylic alcohols to carbonyl compounds: Synthesis of functionalized cinnamates in one pot
An environmentally benign [Cu(I)]-catalyzed oxidation of activated (benzylic/allylic) alcohols to the corresponding carbonyl compounds is presented. Interestingly, the reaction was also compatible with benzylic alcohols containing ortho-bromo substituents on the aromatic ring without competing with the expected intermolecular Buchwald coupling. Significantly, the catalytic system enables the synthesis of cinnamate-esters in a sequential domino one-pot fashion via oxidation followed by Wittig-Horner protocol. Copyright
Reddy, Alavala Gopi Krishna,Mahendar, Lodi,Satyanarayana, Gedu
supporting information
p. 2076 - 2087
(2014/07/07)

NOVEL METHODS AND INTERMEDIATES FOR THE PREPARATION OF (4BS,5AR)-12-CYCLOHEXYL-N-(N,N-DIMETHYLSULFAMOYL)-3-METHOXY-5A-((1 R,5S) -3-METHYL-3,8-DIAZABICYCLO[3.2.1]OCTANE-8-CARBONYL)-4B,5,5A,6-TETRAHYDROBENZO [3,4]CYCLOPROPA[5,6]AZEPINO[1,2-A]INDOLE-9-CARBOX
The present invention provides methods and intermediates for the preparation of (1aR,12bS)-8-cyclohexyl-11-fluoro-N-((1-methylcyclopropyl)sulfonyl)-1a-((3-methyl-3,8-diazabicyclo[3.2.1]oct-8-yl)carbonyl)-1,1a,2,12b-tetrahydrocyclopropa[d]indolo[2,1-a][2]b
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Page/Page column 16; 17

(2014/02/15)

CRYSTALLINE FORM OF 6-[(4S)-2-METHYL-4-(2-NAPHTHYL)-1,2,3,4-TETRAHYDROISOQUINOLIN-7-YL]PYRIDAZIN-3-AMINE
The present disclosure generally relates to a crystalline form of 6-[(4S)-2-methyl-4-(naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine. The present disclosure also generally relates to pharmaceutical compositions comprising the crystalline form, as well of methods of using a crystalline form in the treatment of depression and other conditions and methods for obtaining such crystalline form.
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Paragraph 0072; 0129; 0130

(2014/09/30)

Regioselective electrophilic aromatic bromination: Theoretical analysis and experimental verification
Electrophilic aromatic bromination is the most common synthetic method used to prepare aryl bromides, which are very useful intermediates in organic synthesis. To understand the experimental results in electrophilic aromatic brominations, ab initio calculations are used here for a tentative analysis of the positional selectivity. The calculated results agree well with the corresponding experimental data, and the reliability of the resulting positional selectivity was verified by the corresponding experimental data.
Li, Hui-Jing,Wu, Yan-Chao,Dai, Jian-Hong,Song, Yan,Cheng, Runjiao,Qiao, Yuanyuan
p. 3401 - 3416
(2014/04/17)

Intriguing substituent effect in modified Hoveyda-Grubbs metathesis catalysts incorporating a chelating iodo-benzylidene ligand
A series of modified Hoveyda-Grubbs catalysts incorporating a chelating iodo-benzylidene ligand were prepared and characterized. The presence of electron-withdrawing ring substituents in the para position to the iodide was found to decrease the catalytic activity, revealing that dissociation of the Ru...I-Ar bond is not the rate-determining step.
Barbasiewicz, Michal,Blocki, Krzysztof,Malinska, Maura,Pawlowski, Robert
supporting information
p. 355 - 358
(2013/02/22)

Synthesis, topoisomerase-targeting activity and growth inhibition of lycobetaine analogs
The plant alkaloid lycobetaine has potent topoisomerase-targeting properties and shows anticancer activity. Based on these findings, several lycobetaine analogs were synthesized mainly differing in their substituents at 2, 8 and 9 position and their biological activities were evaluated. The topoisomerase-targeting properties and cytotoxicity of these structural analogs were assessed in the human gastric carcinoma cell line GXF251L. Performing a plasmid relaxation assay, an increased inhibition of topoisomerase I was found with N-methylphenanthridinium chlorides bearing a 8,9-methylenedioxy moiety or a methoxy group in 2-position. Furthermore, quaternized phenanthridinium derivatives bearing either a 2-methoxy or a 8,9-methylenedioxy moiety in conjunction with a 2-hydroxy or 2-methoxy group display potent topoisomerase II inhibition as shown by decatenation of kinetoplast DNA. In general, the N-methylphenanthridinium chlorides possess more potency in inhibiting topoisomerase I than topoisomerase II. All quaternized derivatives also exhibited potent inhibition of tumor cell growth in the low micromolar concentration range. Hence, N-methylphenanthridinium compounds were found to represent a promising class of compounds, potently inhibiting both, topoisomerases I and II, and may be further developed into clinically useful topoisomerase inhibitors.
Baechler, Simone A.,Fehr, Markus,Habermeyer, Michael,Hofmann, Andreas,Merz, Karl-Heinz,Fiebig, Heinz-Herbert,Marko, Doris,Eisenbrand, Gerhard
supporting information
p. 814 - 823
(2013/02/25)

Synthesis of (Z) isomers of benzoheterocyclic derivatives of combretastatin A-4: A comparative study of several methods
Several methods for the preparation of (Z) trimethoxystyrene derivatives 1 were investigated. After finding that the Wittig reaction led to unsatisfactory results, three different strategies were considered: a Suzuki coupling with a stereodefined monobromoalkene, a combination of hydrosilylation/vinylsilane hydrolysis and a palladium-catalyzed semi-hydrogenation step, using DMF/KOH as the hydrogen source. Our studies led us to prepare a series of diarylacetylene derivatives via a Sonogashira coupling reaction, and also to find out a copper-free basic cyclization leading to benzo[b]thiophenes. The final choice for the synthesis method of 1 strongly depends on the target compound but the semi-hydrogenation, which avoids the use of a toxic tin reducing agent, should be generally preferred.
Nguyen, Thi Thanh Binh,Lomberget, Thierry,Tran, Ngoc Chau,Barret, Roland
p. 2336 - 2347
(2013/03/29)

Identification of fused-ring alkanoic acids with improved pharmacokinetic profiles that Act as G protein-coupled receptor 40/free fatty acid receptor 1 agonists
The G protein-coupled receptor 40 (GPR40)/free fatty acid receptor 1 (FFA1) has emerged as an attractive target for a novel insulin secretagogue with glucose dependency. We previously identified phenylpropanoic acid derivative 1 (3-{4-[(2′,6′-dimethylbiphenyl-3-yl)methoxy]-2-fluorophenyl} propanoic acid) as a potent and orally available GPR40/FFA1 agonist; however, 1 exhibited high clearance and low oral bioavailability, which was likely due to its susceptibility to β-oxidation at the phenylpropanoic acid moiety. To identify long-acting compounds, we attempted to block the metabolically labile sites at the phenylpropanoic acid moiety by introducing a fused-ring structure. Various fused-ring alkanoic acids with potent GPR40/FFA1 activities and good PK profiles were produced. Further optimizations of the lipophilic portion and the acidic moiety led to the discovery of dihydrobenzofuran derivative 53 ((6-{[4′-(2-ethoxyethoxy)-2′,6′-dimethylbiphenyl-3-yl]methoxy} -2,3-dihydro-1-benzofuran-3-yl)acetic acid), which acted as a GPR40/FFA1 agonist with in vivo efficacy during an oral glucose tolerance test (OGTT) in rats with impaired glucose tolerance.
Negoro, Nobuyuki,Sasaki, Shinobu,Ito, Masahiro,Kitamura, Shuji,Tsujihata, Yoshiyuki,Ito, Ryo,Suzuki, Masami,Takeuchi, Koji,Suzuki, Nobuhiro,Miyazaki, Junichi,Santou, Takashi,Odani, Tomoyuki,Kanzaki, Naoyuki,Funami, Miyuki,Tanaka, Toshimasa,Yasuma, Tsuneo,Momose, Yu
supporting information; experimental part
p. 1538 - 1552
(2012/04/10)

Tricyclic isoindolines by Heck cyclization
A series of 4-formyl esters 8a-d was prepared by Michael addition of an enamine with ethyl acrylate. A subsequent condensation with 2-bromobenzylamines 3 gave rise to cyclic enamides 9aa-dd. In a Heck cyclization reaction tricyclic isoindoles 10aa-dd were formed in good yields.
Satyanarayana, Gedu,Maier, Martin E.
scheme or table
p. 1745 - 1749
(2012/03/10)

Copper-catalyzed recycling of halogen activating groups via 1,3-halogen migration
A Cu(I)-catalyzed 1,3-halogen migration reaction effectively recycles an activating group by transferring bromine or iodine from a sp2 to a benzylic carbon with concomitant borylation of the Ar-X bond. The resulting benzyl halide can be reacted in the same vessel under a variety of conditions to form an additional carbon-heteroatom bond. Cross-over experiments using an isotopically enriched bromide source support intramolecular transfer of Br. The reaction is postulated to proceed via a Markovnikov hydrocupration of the o-halostyrene, oxidative addition of the resulting Cu(I) complex into the Ar-X bond, reductive elimination of the new sp3 C-X bond, and final borylation of an Ar-Cu(I) species to turn over the catalytic cycle.
Grigg, R. David,Van Hoveln, Ryan,Schomaker, Jennifer M.
supporting information
p. 16131 - 16134,4
(2020/09/09)

Hydrogen-bonding catalysis and inhibition by simple solvents in the stereoselective kinetic epoxide-opening spirocyclization of glycal epoxides to form spiroketals
Mechanistic investigations of a MeOH-induced kinetic epoxide-opening spirocyclization of glycal epoxides have revealed dramatic, specific roles for simple solvents in hydrogen-bonding catalysis of this reaction to form spiroketal products stereoselectively with inversion of configuration at the anomeric carbon. A series of electronically tuned C1-aryl glycal epoxides was used to study the mechanism of this reaction based on differential reaction rates and inherent preferences for SN2 versus SN1 reaction manifolds. Hammett analysis of reaction kinetics with these substrates is consistent with an SN2 or SN2-like mechanism (ρ = -1.3 vs ρ = -5.1 for corresponding SN1 reactions of these substrates). Notably, the spirocyclization reaction is second-order dependent on MeOH, and the glycal ring oxygen is required for second-order MeOH catalysis. However, acetone cosolvent is a first-order inhibitor of the reaction. A transition state consistent with the experimental data is proposed in which one equivalent of MeOH activates the epoxide electrophile via a hydrogen bond while a second equivalent of MeOH chelates the side-chain nucleophile and glycal ring oxygen. A paradoxical previous observation that decreased MeOH concentration leads to increased competing intermolecular methyl glycoside formation is resolved by the finding that this side reaction is only first-order dependent on MeOH. This study highlights the unusual abilities of simple solvents to act as hydrogen-bonding catalysts and inhibitors in epoxide-opening reactions, providing both stereoselectivity and discrimination between competing reaction manifolds. This spirocyclization reaction provides efficient, stereocontrolled access to spiroketals that are key structural motifs in natural products.
Wurst, Jacqueline M.,Liu, Guodong,Tan, Derek S.
p. 7916 - 7925
(2011/07/08)

SYNTHESIS OF THE POTENT IMMUNOSUPPRESSANT AGENTS DALESCONOL A AND B
This invention relates to compounds having the structure: wherein bonds α, β, γ, δ, ω, η, χ, ε, κ, and μ are each present or absent, and R1-R18 are various substituents described herein.
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Page/Page column 62-63

(2011/09/19)

Total synthesis of plagiochin D by an intramolecular SNAr reaction
The total synthesis of plagiochin D, a macrocyclic bis(bibenzyl) compound isolated from the liverwort plagiochila acanthophylla, has been accomplished. Closure of the key 16-membered ring, which contained biphenyl ether and biaryl units, was achieved in good yield by an intramolecular SNAr reaction. The Suzuki and Wittig protocols proved to be powerful tools for the construction of a linear precursor that was crucial for ring cyclization. Copyright
Cortes Morales, Julio Cesar,Guillen Torres, Alejandro,Gonzalez-Zamora, Eduardo
scheme or table
p. 3165 - 3170
(2011/06/28)

Efficient discovery of fluorescent chemosensors based on a biarylpyridine scaffold
(Figure Presented) The discovery of several fluorescent chemosensors for Hg(II) and Ag(I) In mixed aqueous solution Is reported. The ease with which these fluorlonophores were prepared from a common core underscores the utility of conformational restriction as a signaling mechanism. In addition, for the first time, significant changes were observed In biarylpyridlne emission wavelength, allowing ratlometric detection of Hg(II) and Ag(I). Finally, on the basis of computational analyses, beneficial structural modifications were predicted for the next generation of chemosensors.
Malashikhin, Sergey A.,Baldridge, Kim K.,Finney, Nathaniel S.
supporting information; experimental part
p. 940 - 943
(2010/06/16)

Syntheses of macrocyclic bis(bibenzyl) compounds derived from perrottetin e
Macrocyclic bis(bibenzyl) compounds are natural products from liverworts and are of growing interest due to recent reports on new isolated compounds and on their remarkable biological activities. We report here on a flexible and general approach to the to
Speicher, Andreas,Groh, Matthias,Hennrich, Markus,Huynh, Anh-Minh
experimental part
p. 6760 - 6778
(2011/03/18)

Total syntheses of dalesconol A and B
(Chemical equation Presented) (Chemical equation Presented) A polycyclic collapse: Use of a carefully designed acyclic intermediate participated in a cascade reaction that formed the entire core of the polyketide-derived dalesconols in a single flask (see scheme). A number of additional and carefully controlled synthetic operations completed an expeditious synthesis of both of these highly bioactive natural products as well as structural congenors.
Snyder, Scott A.,Sherwood, Trevor C.,Ross, Audrey G.
supporting information; experimental part
p. 5146 - 5150
(2010/11/04)

An efficient regioselective NBS aromatic bromination in the presence of an ionic liquid
A simple, efficient, and rapid method was developed for high-yielding regioselective monobromination of activated aromatic compounds using NBS in combination with ionic liquid 1-butyl-1-methylimidazolium bromide ([Bmim]Br) or dioxane. The ionic liquid is recyclable and can be reused with minimal loss in the catalytic efficiency if the ionic liquid is rapidly microwaved prior to reactions.
Pingali, Subramanya R.K.,Madhav, Monika,Jursic, Branko S.
experimental part
p. 1383 - 1385
(2010/04/25)

NHC-catalyzed spiro bis-indane formation via domino stetter - Aldol - Michael and stetter - Aldol - Aldol reactions
Two novel domino NHC-catalyzed spirocyclizations are described herein, enabling the rapid construction of three new carbon - carbon bonds and a quaternary center with high diastereoselectivity. A variety of spiro bis-indane structures are assembled in a single step from simple o-phthaldialdehyde derivatives.
Sanchez-Larios, Eduardo,Holmes, Janice M.,Daschner, Crystal L.,Gravel, Michel
supporting information; experimental part
p. 5772 - 5775
(2011/03/22)

A synthesis-driven structure revision of 'plagiochin E', a highly bioactive bisbibenzyl
Recently, a bisbibenzyl named plagiochin E showing remarkable antifungal and antitumor activities was isolated from Marchantia polymorpha, a liverwort. The total synthesis of the proposed structure for plagiochin E and of two structurally and biosynthetic
Speicher, Andreas,Groh, Matthias,Zapp, Josef,Schauml?ffel, Anu,Knauer, Michael,Bringmann, Gerhard
scheme or table
p. 1852 - 1858
(2009/12/05)

CRYSTALLINE FORM OF 6-[(4S)-2-METHYL-4-(2-NAPHTHYL)-1,2,3,4-TETRAHYDROISOQUINOLIN-7-YL]PYRIDAZIN-3-AMINE
The present disclosure generally relates to a crystalline form of 6-[(4S)-2-methyl-4-(naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine. The present disclosure also generally relates to pharmaceutical compositions comprising the crystalline form, as well of methods of using a crystalline form in the treatment of depression and other conditions and methods for obtaining such crystalline form.
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Page/Page column 22; 42-43

(2009/12/28)

Nucleophilic substitution of nitro groups by [18F]fluoride in methoxy-substituted ortho-nitrobenzaldehydes-A systematic study
As model reactions for the introduction of [18F]fluorine into aromatic amino acids, the replacement of NO2 by [18F]fluoride ion in mono- to tetra-methoxy-substituted ortho-nitrobenzaldehydes was systematically investigated. Unexpectedly, the highly methoxylated precursors 2,3,4-trimethoxy-6-nitrobenzaldehyde and 2,3,4,5-tetramethoxy-6-nitrobenzaldehyde showed high maximum radiochemical yields (82% and 48% respectively). When the electrophilicity of the leaving group substituted carbon atom is expressed by its 13C NMR chemical shift a good correlation with the reaction rate at the beginning of the reaction (first min) was found (R2 = 0.89), whereas the maximum radiochemical yields correlated much poorer with this electrophilicity parameter. This may be caused by side reactions becoming influencial in the further reaction course. As possible side reactions the demethylation of methoxy groups and intramolecular redox reactions could be detected by HPLC/MS.
Shen, Bin,L?ffler, Dirk,Reischl, Gerald,Machulla, Hans-Jürgen,Zeller, Klaus-Peter
experimental part
p. 216 - 224
(2009/07/25)

Synthesis of arylbromides from arenes and Nbromosuccinimide bromosuccinimide (NBS) in acetonitrile - A convenient method for aromatic bromination
Regioselective and chemoselective electrophilic bromination of a wide series of activated arenes using N-bromosuccinimide (NBS) in acetonitrile occurs readily. Environmentally friendly conditions, large substrate scope, and ease of synthesis enhance the utility of this method over other electrophilic bromination conditions.
Zysman-Colman, Eli,Arias, Karla,Siegel, Jay S.
experimental part
p. 440 - 447
(2009/12/01)

TOTAL SYNTHESIS OF ENANTIOPURE DESOGESTREL
The present invention relates to a total synthesis of desogestrel and derivatives thereof, and to intermediate compounds of this synthesis.
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Page/Page column 25

(2009/04/25)

DIAMINOPROPANE DERIVED MACROCYCLES AS INHIBITORS OF BETA AMYLOID PRODUCTION
There is provided a series of macrocyclic diaminopropanes of Formula (I) or a stereoisomer; or a pharmaceutically acceptable salt thereof, wherein R1, R2, R3, m, n, W, X, Y, Z and L as defined herein, their pharmaceutical compositions and methods of use. These novel compounds inhibit the processing of amyloid precursor protein (APP) by β-secretase and, more specifically, inhibit the production of Aβ-peptide. The present disclosure is directed to compounds useful in the treatment of neurological disorders related to β-amyloid production, such as Alzheimer's disease and other conditions affected by anti-amyloid activity.
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Page/Page column 30

(2008/12/07)

Enantioselective total synthesis of the oral contraceptive desogestrel by a double heck reaction
A novel enantioselective total synthesis of the oral contraceptive desogestrel (2) is described, in which the tetracyclic steroid core is formed by a sequence of two consecutive Heck reactions. Conversion of the known enantiopure diketone 7 led to the chiral bicycle 6 which was used for a diastereoselective intermolecular Heck reaction with vinyliodide 5 to give 15. In the following intramolecular Heck reaction, the tetracyclic ring system was formed to give 4, from which the synthesis of desogestrel (2) was furnished.
Tietze, Lutz F.,Krimmelbein, Ilga K.
experimental part
p. 1541 - 1551
(2009/04/04)

QUINOLINONE DERIVATIVES
HIV inhibitory compounds of formula (I) including the stereoisomeric forms thereof, the pharmaceutically acceptable salts, and pharmaceutically acceptable solvates thereof; wherein R1 is cyano; R2 is H, C1-6alkyl, trifluoromethyl, amino, mono- or di-C1-6alkylamino, C1-6alkylamino wherein the C1-6alkyl group can be substituted; X1 is CH or N; R3 is phenyl or pyridyl, each unsubstituted or substituted; R4 is H, C1-6alkyl, (C1-6alkylcarbonyla mino)C1-6alkyl-, Ar, potionally substituted thienyl, furanyl, pyridyl, pyrimidyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazo lyl, oxazolyl, thiazolyl, halo, trifluoromethyl, hydroxy, C1-6alkyloxy, -OPO(OH)2, amino, aminocarbonyl, cyano, -Y1-R6, -Y1-Alk-R6, or -Y1-Alk-Y2-R7; R5 is H, halo, hydroxy or C1-6alkyloxy; or R4 and R5 form -O-CH2-O-; Y1 is O or NR8; Y2 is O or NR9; Alk is bivalent C1-6alkyl; R6 is pyrrolidinyl, piperidinyl, morpho linyl, piperazinyl, 4-C1 -6alkylpiperazinyl, 4-(C1-6alkylcarbonyl)piperazinyl, pyridyl, or imidazolyl; R7 is H, C1-6alkyl, hydroxyC1 -6alkyl, C1-6alkylcarbonyl; R8 and R9 are H or C1-6alkyl; Ar is optionally substituted phenyl; pharmaceut ical compositions comprising the above compounds (I) as active ingredient.
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Page/Page column 46

(2008/06/13)

Synthesis of novel spinosyn a analogues by Pd-mediated transformations
The concept of modern crop protection demands for a continuous supply of new or modified established pesticides to avoid the development of serious resistances. Recent reports on the insecticidal spinosyns 1 and 2 show that also this class of pest managing agents is increasingly exposed to the formation of resistances. The synthesis of new derivatives is therefore highly desirable. We describe in this paper a convergent approach towards novel enantiopure spinosyn A analogues of type 3, which is based on investigations of structure-activity relationships and employs a twofold Heck reaction as key step for the preparation of the tricyclic backbone assembly.
Tietze, Lutz F.,Brasche, Gordon,Grube, Alexander,Boehnke, Niels,Stadler, Christian
p. 8543 - 8563
(2008/04/01)

Photoinduced C-Br homolysis of 2-bromobenzophenones and Pschorr ring closure of 2-aroylaryl radicals to fluorenones
(Chemical Equation Presented) A variety of diversely substituted 2-aroylaryl radicals, generated by photoinduced homolysis of 2-bromoarylketones, is shown to undergo Pschorr cyclization to yield fluorenones in moderate to excellent yields. The photochemical results illustrate that the substituents in the two phenyl rings of the 2-bromobenzophenone skeleton exert a dramatic influence on the reactivity of the derived 2-aroylaryl radicals. The disubstitution by methoxy groups in the radical ring renders the aryl σ-radical highly electrophilic and unreactive for hydrogen abstraction and cyclization. On the other hand, the substituents in the non-radical ring that strongly stabilize the hydrofluorenyl π-radical, formed subsequent to the attack of the 2-aroylaryl radical on the non-radical ring, promote cyclization to furnish fluorenones in excellent isolated yields.
Moorthy, Jarugu Narasimha,Samanta, Subhas
p. 9786 - 9789
(2008/03/17)

Metal-catalyzed cycloisomerization of enyne functionalities via a 1,3-alkylidene migration
We report a new metal-catalyzed 6-endo-dig cyclization of cis-4,6-dien-1-yn-3-ols, which produces substituted benzene and naphthalene derivatives with structural reorganization. In this process, we observe a 1,3-alkylidene migration via cleavage of the olefin double bond of the starting substrates. The ease and reliability of this cyclization are manifested by its compatibility with a wide array of diverse substrates and several π-alkyne activators, including PtCl2, Zn(OTf)2, AuCl, and AuCl3. Copyright
Lin, Ming-Yuan,Das, Arindam,Liu, Rai-Shung
p. 9340 - 9341
(2007/10/03)

Synthesis and biological activity of allosteric modulators of GABA B receptors, Part 1. N-(Phenylpropyl)-1-arylethylamines
A series of 15 analogues of fendiline, and 34 derivatives of N-(3-phenylpropyl)-1-arylethylamine have been prepared for evaluation as positive allosteric modulators of GABAB receptors. The most active (EC50, 10 nM) was N-(3,3-diphenylpropyl)-1-(3-chloro-4-methoxyphenyl) ethylamine 6g. CSIRO 2006.
Kerr, David I. B.,Ong, Jennifer,Perkins, Michael V.,Prager, Rolf H.,Puspawati, Ni Made
p. 445 - 456
(2007/10/03)

Reversing the discovery paradigm: A new approach to the combinatorial discovery of fluorescent chemosensors
We report here a new approach to the discovery of fluorescent chemosensors in which a new signaling mechanism allows a core fluorophore to be used in a combinatorial search for new binding events, thus reversing the reigning discovery paradigm. Copyright
Mello, Jesse V.,Finney, Nathaniel S.
p. 10124 - 10125
(2007/10/03)

Novel heterocyclic compounds, method for preparing same and use thereof as medicines, in particular as antibacterial agents
The invention relates to new heterocyclic compounds of general formula (I), and their salts with a base or an acid: The invention also relates to a process for the preparation of these compounds, as well as their use as medicaments, in particular as anti-bacterial agents.
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Page/Page column 50-51

(2010/02/14)

Tandem Enyne Metathesis-Diels-Alder Reaction for Construction of Natural Product Frameworks
Enynes connected through aromatic rings are used as substrates for metathesis reactions. The reactivity of three ruthenium carbene complexes is compared. The resulting 1,3-dienes are suitable precursors of polycyclic structures via a Diels-Alder process.
Rosillo, Marta,Dominguez, Gema,Casarrubios, Luis,Amador, Ulises,Perez-Castells, Javier
p. 2084 - 2093
(2007/10/03)

Efficient synthesis of isoplagiochin D, a macrocyclic bis(bibenzyls), by utilizing an intramolecular Suzuki-Miyaura reaction
Isoplagiochin D, a highly strained macrocyclic bis(bibenzyls) isolated from the liverwort Pladiochila fruticosa, was synthesized in 10.6% overall yield for the 11 steps by using Horner-Wadsworth-Emmons and Suzuki-Miyaura protocols. Isoplagiochin D, a highly strained macrocyclic bis(bibenzyls) with two biaryl units isolated from the liverwort Pladiochila fruticosa, was prepared in 10.6% overall yield for the 11 steps by an efficient synthetic approach involving the construction of two bibenzyl and one biaryl units using Horner-Wadsworth-Emmons and Suzuki-Miyaura protocols.
Esumi, Tomoyuki,Wada, Mitsumasa,Mizushima, Eri,Sato, Norimasa,Kodama, Mitsuaki,Asakawa, Yoshinori,Fukuyama, Yoshiyasu
p. 6941 - 6945
(2007/10/03)