- Bromination of α-Diazo Phenylacetate Derivatives Using Cobalt(II) Bromide
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A method for the bromination of α-diazo phenylacetate derivatives using cobalt(II) bromide is described. This bromination reaction features a short reaction time, broad substrate scope, operational simplicity, acid-free conditions, and gram-scalability. (Figure presented.).
- Wang, Haifeng,Sun, Xiangli,Hu, Manman,Zhang, Xiaoyi,Xie, Lele,Gu, Shuangxi
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supporting information
p. 3347 - 3351
(2020/07/04)
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- Regioselective and Stereoselective Heck-Matsuda Arylations of Trisubstituted Allylic Alkenols and Their Silyl and Methyl Ether Derivatives to Access Two Contiguous Stereogenic Centers: Expanding the Redox-Relay Process and Application in the Total Synthesis of meso-Hexestrol
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Novel palladium-catalyzed redox-relay Heck arylation reactions of trisubstituted allylic alkenols were developed employing silyl and methyl ethers. The reactions proceeded under mild conditions in moderate to high yields in an excellent anti diastereoselectivity to form α,β-disubstituted methyl ketones containing two contiguous stereocenters. The new redox-relay arylations using silyl and methyl ethers of the starting alkenols demonstrate that the presence of a free hydroxyl group is not a sine qua non condition for an effective redox-relay process as previously thought. Deuterium-labeled alkenols 2-d-10a, 2-d-10b, and 2-d-10c permitted tracking the palladium-hydride reinsertion steps in the conversion of the starting free alcohols, silyl, and methyl ethers into the corresponding methyl ketone 3-d-11a, with >98% deuterium retention. Moreover, the synthetic potential of the method was demonstrated with a straightforward synthesis of the meso-hexestrol in 4 steps, in 41% overall yield from alkenol 10a.
- Frota, Carlise,Polo, Ellen Christine,Esteves, Henrique,Correia, Carlos Roque Duarte
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p. 2198 - 2209
(2018/02/23)
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- Mechanochromic Polymers That Turn Green Upon the Dissociation of Diarylbibenzothiophenonyl: The Missing Piece toward Rainbow Mechanochromism
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Mechanochromic polymers, that is, polymers sensitive to mechanical impact, promise great potential for applications in damage sensors. In particular, radical-type mechanochromic polymers, which produce colored radical species in response to mechanical str
- Ishizuki, Kuniaki,Oka, Hironori,Aoki, Daisuke,Goseki, Raita,Otsuka, Hideyuki
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supporting information
p. 3170 - 3173
(2018/02/09)
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- Pd-catalyzed divergent C(sp2)-H Activation/Cycloimidoylation of 2-Isocyano-2,3-diarylpropanoates
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A Pd-catalyzed site-selective C(sp2)-H activation/cycloimidoylation of 2-isocyano-2,3-diarylpropanoates to construct diverse cyclic imine products has been developed. Six-membered 3,4-dihydroisoquinolines containing a C3 quaternary carbon cente
- Tang, Shi,Yang, Sheng-Wen,Sun, Hongwei,Zhou, Yali,Li, Juan,Zhu, Qiang
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supporting information
p. 1832 - 1836
(2018/04/14)
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- Construction of Pyrrolo[1,2-a]indoles via Cobalt(III)-Catalyzed Enaminylation of 1-(Pyrimidin-2-yl)-1H-indoles with Ketenimines and Subsequent Base-Promoted Cyclization
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A cobalt(III)-catalyzed cross-coupling reaction of 1-(pyrimidin-2-yl)-1H-indoles with ketenimines is reported. The reaction provided 2-enaminylated indole derivatives in moderate to excellent yields with a broad substrate scope. The prepared 2-enaminylated indoles could be conveniently converted into pyrrolo[1,2-a]indoles, which are an important class of compounds in medicinal chemistry.
- Zhou, Xiaorong,Fan, Zili,Zhang, Zhiyin,Lu, Ping,Wang, Yanguang
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supporting information
p. 4706 - 4709
(2016/09/28)
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- Synthesis of α,α-disubstituted α-amino esters: Nucleophilic addition to iminium salts generated from amino ketene silyl acetals
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Alkoxycarbonyl iminium species are prepared easily by the oxidation of tetrasubstituted amino ketene silyl acetals, and subsequent nucleophilic addition of Grignard reagents to the iminium salts gives α,α- disubstituted α-amino ester derivatives in moderate to good yields, in which aryl and ethynyl substituents are readily introduced.
- Hata, Shingo,Koyama, Hiroshi,Shimizu, Makoto
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experimental part
p. 9670 - 9677
(2012/01/04)
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- Generation of iminyl copper species from α-azido carbonyl compounds and their catalytic C-C bond cleavage under an oxygen atmosphere
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Figure presented A copper-catalyzed reaction of α-azidocarbonyl compounds under an oxygen atmosphere is reported where nitriles are formed via C-C bond cleavage of a transient iminyl copper intermediate. The transformation is carried out by a sequence of denitrogenative formation of iminyl copper species from α-azidocarbonyl compounds and their C-C bond cleavage, where molecular oxygen (1 atm) is a prerequisite to achieve the catalytic process and one of the oxygen atoms of O2 was found to be incorporated into the β-carbon fragment as a carboxylic acid.
- Chiba, Shunsuke,Zhang, Line,Ang, Gim Yean,Hui, Benjamin Wei-Qiang
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supporting information; experimental part
p. 2052 - 2055
(2010/07/04)
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- TRANSLOCATOR PROTEIN LIGANDS
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The present invention relates to compounds and methods for imaging translocator protein (18 kDa) (TSPO) expression in a subject. This invention also relates to compounds and methods for the treatment of neurodegenerative disorders, inflammation or anxiety in a subject.
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Page/Page column 44-46
(2009/07/25)
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- Iminyl radicals from α-azido o-iodoanilides via 1,5-H transfer reactions of aryl radicals: New transformation of α-azido acids to decarboxylated nitriles
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(Chemical Equation Presented) The radical reaction of tributyltin hydride with o-iodo-N-methylanilides derived from α-azido acids provides an excellent access to α-(aminocarbonyl)iminyl radicals through 1,5-hydrogen transfer reaction of initially formed aryl radicals followed by β-elimination of dinitrogen from ensuing α-azido-α- (aminocarbonyl)alkyl radicals. The outcoming iminyls display a peculiar tendency to form corresponding nitriles by β-elimination of aminocarbonyl radicals.
- Bencivenni, Giorgio,Lanza, Tommaso,Leardini, Rino,Minozzi, Matteo,Nanni, Daniele,Spagnolo, Piero,Zanardi, Giuseppe
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p. 4721 - 4724
(2008/09/21)
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- Reliable and versatile synthesis of 2-aryl-substituted cinnamic acid esters
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2-Aryl-substituted phosphono acetates can be readily synthesized by a four-step sequence from the respective arenes. Succeeding Horner-Wadsworth- Emmons olefinations provide stereoselectively the 2-aryl cinnamic acid esters even when sensitive moieties are involved. Georg Thieme Verlag Stuttgart.
- Ianni, Alen,Waldvogel, Siegfried R.
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p. 2103 - 2112
(2008/02/02)
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- Diastereochemical diversity of imidazoline scaffolds via substrate controlled TMSCI mediated cycloaddition of azlactones
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(Chemical Equation Presented) We report herein a trimethylsilyl chloride mediated substrate controlled 1,3-dipolar cycloaddition for the diastereoselective synthesis of either syn- or anti-imidazolines. This method provides scaffolds with four points of diversity and control over two stereocenters.
- Sharma, Vasudha,Tepe, Jetze J.
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p. 5091 - 5094
(2007/10/03)
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- Method for treating emesis with ghrelin agonists
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The present invention relates to a method comprising administering to a patient diagnosed as being in need of treatment for nausea, emesis, or symptoms associated therewith comprising administering to a patient in need thereof a compound of formula (I) wh
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Page/Page column 5
(2010/02/15)
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- Growth hormone secretagogues
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What is disclosed are growth hormone secretagogues, and their uses, of the formula wherein R1 is C6H5CH2OCH2—, C6H5(CH2)3— or indol-3-ylmethyl; Y is pyrrolidin-1-yl, 4-C1-C6alkylpiperidin-1-yl or NR2R2; R2 are each independently a C1to C6alkyl; R3 is 2-napthyl or phenyl para-substituted by W; W is H, F, CF3, C1-C6alkoxy or phenyl; and R4 is H or CH3, or a pharmaceutically acceptable salt or solvate thereof.
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Page column 29
(2010/02/09)
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- Synthesis and biological evaluation of an orally active ghrelin agonist that stimulates food consumption and adiposity in rats
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LY444711 is an orally active ghrelin agonist that binds with good affinity and is a potent activator of the growth hormone secretagogue receptor 1a (GHS-R1a) receptor. In rat models of feeding behavior and pharmacology, LY444711 creates a positive energy
- Lugar, Charles W.,Clay, Michael P.,Lindstrom, Terry D.,Woodson, Andrea L.,Smiley, David,Heiman, Mark L.,Dodge, Jeffrey A.
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p. 5873 - 5876
(2007/10/03)
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- A novel palladium-catalyzed homocoupling reaction initiated by transmetallation of palladium enolates
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Palladium-catalyzed homocoupling reaction of aryl boronic acids has been developed using a protocol similar to the well-documented crosscoupling reaction. α-Halocarbonyl compounds are applied to initiate the reaction via oxidative addition to a palladium(0) species. The resulting palladium enolate halide can promote the double transmetallation. Reductive elimination generates the desire homocoupling product.
- Lei, Aiwen,Zhang, Xumu
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p. 2525 - 2528
(2007/10/03)
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- Research on compounds with psychotropic activity IX - synthesis of 6-p-methoxyphenylpyrrolo[2,1-d][1,5]benzothiazepines and evaluation of their affinities for BDZ and GABA receptor subtypes
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6-p-Methoxyphenylpyrrolo[2,1-d][1,5]benzothiazepin-7(6H)-one (IV), cis-7-acetoxy-6,7-dihydro-6-p-methoxyphenylpyrrolo[2,1- d][1,5]benzothiazepine (V) and some significant 7-acyloxy-6-p-methoxyphenylpyrrolo[2,1- d][1,5]benzothiazepines (VI a-g) were synthe
- Nacci,Fiorini,Garofalo,Cagnotto
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p. 545 - 557
(2007/10/02)
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- Phenoxyphenylacetates for use as potential modulators of arichidonic acid pathways
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This invention relates to new lipoxygenase inhibitors possessing anti-inflammatory and anti-allergic properties. The present new compounds are of the formula: STR1 and salts thereof; wherein Ar is phenyl, naphthyl or sulfur, oxygen or nitrogen heterocycli
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- 1-Aryl-3-azabicyclohexanes, a New Series of Nonnarcotic Analgesic Agents
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A series of 1-aryl-3-azabicyclohexanes was synthesized by hydride reduction of 1-arylcyclopropanedicarboximides.Hydroxyphenyl analogues 20, 22, and 24 were prepared by EtSNa-DMF ether cleavage of the corresponding methoxyphenyl analogues 2m, 2n, and 23, respectively, with the secondary amines 20 and 22 going through the N-formyl intermediates 19 and 21.The p-ethoxy analogue 26 was obtained by O-ethylation of 19, followed by base hydrolysis of the amide 25.The greatest analgesic potency in mouse writhing and rat paw-pain assays was observed for para-substituted compounds.Bicifadine, 1-(4-methylphenyl)-3-azabicyclohexane (2b), was the most potent member of the series and is presently undergoing clinical trials in man.Analgesic activity of 2b is limited to the (+) enantiomer 2v, which has the 1R,5S absolute configuration as determined by single-crystal X-ray analysis.The N-methyl analogue (27d) of 2b showed significant analgesic potency, whereas the N-allyl (27a), N-(cyclopropylmethyl) (27b), and N-(n-hexyl) (27c) analogues were inactive.Bicifadine (2b) showed a nonnarcotic profile different from analogous azabicycloalkane and 3-phenylpyrrolidine analgesics.
- Epstein, Joseph W.,Brabander, Herbert J.,Fanshawe, William J.,Hofmann, Corris M.,McKenzie, Thomas C.,et al.
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p. 481 - 490
(2007/10/02)
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