- Electrochemical Generation of Hypervalent Bromine(III) Compounds
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In sharp contrast to hypervalent iodine(III) compounds, the isoelectronic bromine(III) counterparts have been little studied to date. This knowledge gap is mainly attributed to the difficult-to-control reactivity of λ3-bromanes as well as to their challenging preparation from the highly toxic and corrosive BrF3 precursor. In this context, we present a straightforward and scalable approach to chelation-stabilized λ3-bromanes by anodic oxidation of parent aryl bromides possessing two coordinating hexafluoro-2-hydroxypropanyl substituents. A series of para-substituted λ3-bromanes with remarkably high redox potentials spanning a range from 1.86 V to 2.60 V vs. Ag/AgNO3 was synthesized by the electrochemical method. We demonstrate that the intrinsic reactivity of the bench-stable bromine(III) species can be unlocked by addition of a Lewis or a Br?nsted acid. The synthetic utility of the λ3-bromane activation is exemplified by oxidative C?C, C?N, and C?O bond forming reactions.
- Francke, Robert,Mohebbati, Nayereh,Sokolovs, Igors,Suna, Edgars
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supporting information
p. 15832 - 15837
(2021/06/14)
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- Synthesis of the Proposed Structure of Afzeliindanone
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A synthesis of the proposed structure of afzeliindanone was achieved by using an alkyne [2+2+2]-cyclotrimerization as a key step. The data for the synthetic material were found not to match those for the natural material, indicating a structural misassignment.
- Rita, Rita,Rahman, Mohamed Husaini Bin Abdul,Chong, Sherilyn Shi Min,Bates, Roderick W.
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supporting information
p. 1479 - 1481
(2020/09/21)
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- Concise Synthesis of Lamellarin Alkaloids by C-H/N-H Activation: Evaluation of Metal Catalysts in Oxidative Alkyne Annulation
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The performance of various transition-metal catalysts was explored in the step-economical synthesis of naturally occurring lamellarin alkaloids by C-H/N-H activation. The oxidative alkyne annulation proceeded efficiently by using sustainable ruthenium(II) catalysis, which set the stage for a concise synthesis of lamellarin D, lamellarin H and derivatives thereof.
- Mei, Ruhuai,Zhang, Shou-Kun,Ackermann, Lutz
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supporting information
p. 1715 - 1718
(2017/11/27)
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- Three white lignan and simplify structure, its preparation process and its pharmaceutical composition and use thereof
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Disclosed a saucernetin structurally simplified substance and the preparation method and pharmaceutical composition and use thereof. In particular, it relates to a compound of general formula (I) shown as formula (I) or an isomer thereof and a salt thereo
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Paragraph 0081
(2017/01/17)
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- ISOINDOLINE COMPOSITIONS AND METHODS FOR TREATING NEURODEGENERATIVE DISEASE
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Isoindoline sigma-2 receptor antagonist compounds, pharmaceutical compositions comprising such compounds, and methods for inhibiting Abeta- associated synapse loss or synaptic dysfunction in neuronal cells, modulating an Abeta-associated membrane trafficking change in neuronal cells, and treating cognitive decline associated with Abeta pathology are provided.
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Paragraph 0546; 0550
(2015/09/23)
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- Palladium-catalyzed synthesis of benzofurans via C-H activation/oxidation tandem reaction and its application to the synthesis of decursivine and serotobenine
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A new palladium-catalyzed method for the synthesis of benzofurans by reaction of 2-hydroxystyrenes and iodobenzenes via a C-H activation/oxidation tandem reaction has been unprecedentedly discovered. By using this strategy, the overall synthetic efficienc
- Guo, Lei,Zhang, Fengying,Hu, Weimin,Li, Lei,Jia, Yanxing
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supporting information
p. 3299 - 3302
(2014/03/21)
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- The first total synthesis of tarennane, a potent antioxidant chalcone constituent from tarenna attenuate or Magnolia officinalis
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The convergent total synthesis of tarennane has been accomplished in six steps starting from commercially available phloroglucinol and guaiacol; the key step of the synthesis relies on a highly regioselective Heck reaction applying iodophenol and PdCl2(PPh3)2.
- Yang, Jincheng,Yang, Tao,Luo, Youfu,He, Jun,Shi, Jianyou,Peng, Aihua
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scheme or table
p. 258 - 263
(2012/04/18)
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- Green and efficient method for the iodination of phenols in water
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In this article, green conversion of phenols to the corresponding iodide derivatives is reported. The reactions were conducted in water, using potassium iodide as the source of iodine and potassium ferrate as the oxidizing agent. The selected phenols were successfully iodinated in good to excellent yields in mild and non-toxic reaction conditions. Copyright Taylor & Francis Group, LLC.
- Tajik, Hassan,Dadras, Akbar,Hosseini, Abolfazl
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experimental part
p. 258 - 261
(2011/06/26)
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- Regioselective iodination of phenol and analogues using N-iodosuccinimide and p-toluenesulfonic acid
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Mild and highly regioselective monoiodination of phenol and analogues is achieved in high to excellent yields at room temperature with a combination of stoichiometric p-toluenesulfonic acid and N-iodosuccinimide.
- Bovonsombat, Pakorn,Leykajarakul, Juthamard,Khan, Chiraphorn,Pla-on, Kawin,Krause, Michael M.,Khanthapura, Pratheep,Ali, Rameez,Doowa, Niran
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scheme or table
p. 2664 - 2667
(2009/08/09)
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- Synthesis of (S)-imperanene by using allylic substitution
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(Chemical Equation Presented) Synthesis of (S)-imperanene (1) was studied by using copper-assisted allylic substitution of ArCH=CHCH(L)CH2Ar (L: leaving group) and (i-PrO)Me2SiCH2MgCl. Preliminary substitution between PhCH=CHCH(L)Me (L = AcO, PivO, MeOCO2, (2-Py)CO2) and Bu copper reagents derived from BuMgX (X = Br, Cl) and CuBr·Me2S or CuCl in 1:1-40:1 ratios suggested acetate 28 as the best substrate. To prepare 28, kinetic resolution of racemic (E)-TMSCH=CHCH(OH)CH2Ar2 (Ar2 = (p-TBSO)(m-MeO)C6H3) carried out by using the asymmetric epoxidation with (-)-DIPT afforded the corresponding epoxy alcohol and (S)-allylic alcohol. After separation by chromatography, these products were converted to (S,E)-Bu3SnCH=CHCH(OH)CH2Ar2, which upon palladium-catalyzed coupling with Ar2-I followed by acetylation gave 28 (95-98% ee). Substitution of 28 with (i-PrO)Me 2SiCH2MgCl and CuBr·Me2S in a 4:1 ratio at 0°C proceeded cleanly to produce 29 with 100% inversion in 92% yield. Finally, Tamao oxidation furnished 1.
- Takashima, Yuji,Kobayashi, Yuichi
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experimental part
p. 5920 - 5926
(2009/12/26)
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- The synthesis of multiply 13C-labelled plant and mammalian lignans as internal standards for LC-MS and GC-MS analysis
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The syntheses of multiply 13C-labelled derivatives of the two mammalian lignans, enterolactone and enterodiol, and two of their plant lignan precursors, secoisolariciresinol and matairesinol, are described. Three 13C atoms were incorporated into each lignan using potassium [ 13C]cyanide as the source for all of the 13C atoms. The compounds were prepared for use as internal standards in the LC-MS and GC-MS analysis of lignans. Copyright
- Fryatt, Tara,Botting, Nigel P.
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p. 951 - 969
(2007/10/03)
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- Efficient halogenation of aromatic systems using N-halosuccinimides in ionic liquids
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A simple, rapid and highly regioselective green protocol has been developed for the halogenation of aromatic systems with N-halosuccinimides using room temperature ionic liquids (ILs) as novel and recyclable reaction media to produce the corresponding halogenated aromatic compounds in high to quantitative yields. N-Halosuccinimides show enhanced reactivity in ionic liquids thereby reducing the reaction times dramatically and improving the yields substantially.
- Yadav,Reddy,Reddy,Basak,Narsaiah
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- New series of morpholine and 1,4-oxazepane derivatives as dopamine D 4 receptor ligands: Synthesis and 3D-QSAR model
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Since the identification of the dopamine D43 receptor subtype and speculations about its possible involvement in schizophrenia, much work has been put into development of selective D4 ligands. These selective ligands may be effective antipsychotics without extrapyramidal side effects. This work describes the synthesis of a new series of 2,4-disubstituted morpholines and 2,4-disubstituted 1,4-oxazepanes with selectivity for the dopamine D4 receptor. A 3D-QSAR analysis using the GRID/GOLPE methodology was performed with the purpose to get a better understanding of the relationship between chemical structure and biological activity. Inspection of the coefficient plots allowed us to identify that regions which are important for affinity are situated around the two benzene ring systems, a p-chlorobenzyl group, and the aliphatic amine belonging to the morpholine or 1,4-oxazepane system. In addition, the size of the morpholine or 1,4-oxazepane ring seems to be important for affinity.
- Audouze, Karine,Nielsen, Elsebet ?stergaard.,Peters, Dan
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p. 3089 - 3104
(2007/10/03)
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- Enhanced radical-scavenging activity of naturally-oriented artepillin C derivatives
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More than two-fold augmentation in the radical-scavenging activity of artepillin C could be achieved via altering the O-H bond dissociation enthalpy of artepillin C by means of structural modifications. The Royal Society of Chemistry.
- Manda, Sushma,Nakanishi, Ikuo,Ohkubo, Kei,Uto, Yoshihiro,Kawashima, Tomonori,Hori, Hitoshi,Fukuhara, Kiyoshi,Okuda, Haruhiro,Ozawa, Toshihiko,Ikota, Nobuo,Fukuzumi, Shunichi,Anzai, Kazunori
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p. 626 - 628
(2008/09/20)
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- Disubstituted morpholine, oxazepine or thiazepine derivatives, their preparation and their use as dopamine D4 receptor antagonists
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The present invention relates to compounds of formula (I), any of it enantiomers, or any mixture thereof, or a pharmaceutically acceptable acid addition salt thereof, wherein R1, R2, R3, R4, R11, R12, R13, R14and R15each independently are hydrogen, alkyl, alkoxy, halogen, trifluoromethyl, nitro, cyano, amino, acyl, alkylamino, dialkylamino, aminocarbonyl, or acylamino; R5 is hydrogen, alkyl, alkoxyalkyl, or phenylalkyl; X is —CH2—Z—, Z—CH2—, NH—CO—, —CO—NH—, or —CH═CH—; wherein Z is O, S, CH2, or NH; Y is O, —CH2—W—, —W—CH2—; wherein W is O, or S; and n is 0, 1 or 2. The compounds are useful in the treatment of psychotic disorders.
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