- Synthesis, biological evaluation, and docking studies of tetrahydrofuran-cyclopentanone-and cyclopentanol-based ligands acting at adrenergic α1- and serotonine 5-HT1A receptors
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A series of aralkylphenoxyethylamine and aralkylmethoxyphenylpiperazine compounds was synthesized and their in vitro pharmacological profile at both 5-HT1A receptors and α1-adrenoceptor subtypes was measured by binding assay and func
- Prandi, Adolfo,Franchini, Silvia,Manasieva, Leda Ivanova,Fossa, Paola,Cichero, Elena,Marucci, Gabriella,Buccioni, Michela,Cilia, Antonio,Pirona, Lorenza,Brasili, Livio
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- Catalytic and regioselective ring expansion of arylcyclobutanones with trimethylsilyldiazomethane. Ligand-dependent entry to β-ketosilane or enolsilane adducts
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Divergent reactivity is uncovered in the homologation of arylcyclobutanones with trimethylsilyldiazomethane. With Sc(OTf)3 as catalyst, enolsilanes are obtained with a high preference for methylene migration. By contrast, Sc(hfac)3 g
- Dabrowski, Jennifer A.,Moebius, David C.,Wommack, Andrew J.,Kornahrens, Anne F.,Kingsbury, Jason S.
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supporting information; experimental part
p. 3598 - 3601
(2010/11/04)
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- Reactions of methylenecyclobutanes with silver acetate and iodine
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Methylenecyclobutanes undergo an interesting rearrangement reaction in the presence of silver acetate and iodine at room temperature (20 °C) in dichloromethane to give the corresponding aryl-(1-arylcyclobutyl)methanones in good to high yields within short
- Jiang, Min,Liu, Le-Ping,Shi, Min
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p. 9599 - 9604
(2008/02/11)
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- Preparation of Alkylidenecyclobutanes and Their Transformation to 2,2-Disubstituted Cyclopentanones
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The reaction of ketones with the titanocene reagent prepared by the treatment of 1,1-bis(phenylthio)cyclobutane with the low valent titanium species Cp2Ti2 produced the corresponding alkylidenecyclobutanes. These compounds were successfully trans
- Fujiwara, Tooru,Iwasaki, Norie,Takeda, Takeshi
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p. 741 - 742
(2007/10/03)
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- Direct α-arylation of ketones: The reaction of cyclic ketone enolates with diphenyliodonium triflate
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Diphenyliodonium triflate 1a reacts with the lithium enolates of cyclic ketones 2 (ring size = 5 - 8), in the presence of stoichiometric quantities of copper cyanide, to afford the corresponding α-phenylated ketones 3 or α,α'-diphenylated ketones 4.
- Ryan, John H.,Stang, Peter J.
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p. 5061 - 5064
(2007/10/03)
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- Nitroalkene Inter /Intra Tandem Cycloadditions. 7. Application of (R)-(-)-2,2-Diphenylcyclopentanol as the Chiral Auxiliary
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Chiral enol ethers derived from (R)-(-)-2,2-diphenylcyclopentanol ((-)3) have been found to provide high levels of asymmetric induction in tandem inter /intra nitroalkene cycloadditions.The chiral auxiliary (>97percent ee) is readily prepar
- Denmark, Scott E.,Schnute, Mark E.,Marcin, Lawrence R.,Thorarensen, Atli
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p. 3205 - 3220
(2007/10/02)
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- Direct and Regiocontrolled Synthesis of α-Phenyl Ketones from Silyl Enol Ethers and Diphenyliodonium Fluoride
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The efficiacy of diphenyliodonium fluoride (1, DIF) for the phenylation of silyl enol ethers was investigated.When the silyl enol ethers of cyclopentanone, 2-methylcyclopentanone, cyclohexanone, 2-methylcyclohexanone, acetophenone, 2-pentanone, diisopropyl ketone, and pinacolone were mixed with DIF in tetrahydrofuran, either α-phenyl or α,α-diphenyl ketones were produced and isolated in yields ranging from 20 to 88percent.That the regiochemistry of α-phenylation can be controlled by an appropriate choice of silyl enol ether was demonstrated with the kinetic and thermodynamic silyl enol ethers of 2-methylcyclohexanone, the thermodynamic silyl enol ether of 2-methylcyclopentanone, and the kinetic silyl enol ether of 2-pentanone. 3,3-Dimethyl-2-(silyloxy)-1-butene gave a dehydro dimer of pinacolone with DIF in addition to α-phenylpinacolone, thus suggesting that phenylations of silyl enol ethers with DIF may proceed via radical intermediates.
- Chen, Kuanchiang,Koser, Gerald F.
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p. 5764 - 5767
(2007/10/02)
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- Diastereoselectivity in the reduction of sterically unbiased 2,2-diarylcyclopentanones
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Reduction of sterically unbiased 2-phenyl-2-(4-X-phenyl)cyclopentanones 1 (X = NO2, Br, Cl, OCH3, OH, NH2) with either sodium borohydride in methanol or lithium borohydride in tetrahydrofuran at 0°C produced diastereomeric
- Halterman, Ronald L.,McEvoy, Marjorie A.
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p. 6690 - 6695
(2007/10/02)
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- Photochemical Studies of Cyclopropenes and Cyclopentadienes. Mechanistic and Exploratory Organic Photochemistry
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The photochemistry of two vinylcyclopropenes and one cyclopentadiene was investigated.Thus, 3-phenyl-3-(1-phenylvinyl)cyclopropene, 3-phenyl-3-(2,2-diphenylvinyl)cyclopropene, and 2,5,5-triphenylcyclopentadiene were studied.The vinylcyclopropenes were designed with the vinyl moieties being the low-energy chromophores in contrast to previously studied examples where the cyclopropene ? bond is lower in energy.As with previous vinylcyclopropenes, irradiation led to cyclopentadienes and indenes. 2,5,5-Triphenylcyclopentadiene was the main photoproduct of the irradiation of the (diphenylvinyl)cyclopropene. 3-(2,2-Diphenylvinyl)indene was a lesser product that was encountered. 1,2-Diphenylcyclopentadiene, 3-(1-phenylvinyl)indene, and 3,4-diphenyl-1,2,4-pentatriene were formed from direct photolysis of the styryl cyclopropene.Interestingly, the corresponding sensitized irradiation led exclusively to 1,2-diphenylcyclopentadiene.Quantum efficiencies were determined for these reactions.Direct irradiation of 2,5,5-triphenylcyclopentadiene led to novel ring contraction to afford the (diphenylvinyl)cyclopropene.Additionally, phenyl migration was observed, leading to formation of 1,4,5-triphenylcyclopentadiene.Sensitized reaction of 2,5,5-triphenylcyclopentadiene led only to the phenyl migration product.Again quantum yields were determined.The (diphenylvinyl)cyclopropene was labeled in order to ascertain the skeletal change in the rearrangement.Similary, labeling studies were carried out with 2,5,5-triphenylcyclopentadiene, thus allowing delineation of the fate of each carbon.Additionally, studies were carried out independently to generate the 3,5,5-triphenylpentadienyl carbene.The (diphenylvinyl)cyclopropene was the major product along with 2,5,5-triphenylcyclopentadiene and 3-(2,2-diphenylvinyl)indene.
- Zimmerman, H. E.,Kreil, D.J.
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p. 2060 - 2075
(2007/10/02)
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