- Synthesis of Potent and Selective HDAC6 Inhibitors Bearing a Cyclohexane- or Cycloheptane-Annulated 1,5-Benzothiazepine Scaffold
-
Selective inhibitors of histone deacetylase 6 (HDAC6) are an emerging class of pharmaceuticals due to the involvement of HDAC6 in different pathways related to neurodegenerative diseases, cancer, and immunology. Herein, the synthesis of ten new benzohydro
- De Vreese, Rob,Galle, Lisa,Depetter, Yves,Franceus, Jorick,Desmet, Tom,Van Hecke, Kristof,Benoy, Veronick,Van Den Bosch, Ludo,D'hooghe, Matthias
-
-
Read Online
- Preparation and characterization of magnetic graphene nanocomposite containing Cu(proline)2 as catalyst for asymmetric aldol reactions
-
A new catalyst has been prepared via immobilization of Cu(proline)2 complex onto the surface of magnetic graphene. The fabricated nanocatalyst was characterized by Fourier-transform infrared (FT-IR) spectroscopy, powder X-ray diffraction (PXRD) analysis, vibrating-sample magnetometry (VSM), scanning electron microscopy (SEM), energy-dispersive X-ray (EDX) spectroscopy, transmission electron microscopy (TEM), inductively coupled plasma (ICP) techniques, and elemental analysis. Its catalytic performance was investigated in the aldol reaction using a mild and ecofriendly procedure. The synthesized nanocomposite, which contains Cu(II) center as Lewis acid, was found to be an efficient catalyst for asymmetric aldol reactions, affording corresponding aldol products in high yield and excellent enantiomeric excess (> 90?%). The examined catalyst was prepared from low-cost, easily available starting materials and can be readily isolated by magnetic decantation for recycling and reuse in consecutive reactions without significant loss of activity.
- Kooti,Kooshki,Nasiri
-
p. 2641 - 2656
(2019/02/14)
-
- 1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane: An efficient and high oxygen content oxidant in various oxidative reactions
-
Several oxidative approaches namely thiocyanation of aromatic compounds, epoxidation of alkenes, amidation of aromatic aldehydes, epoxidation of α β-unsaturated ketones, oxidation of sulfides to sulfoxides and sulfones, bayer-villeger reaction, bromination and iodation of aniline and phenol derivatives oxidative esterification, oxidation of pyridines and oxidation of secondary, allylic and benzyllic alcohols were carried out using 1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane as the potential solid oxidant which can be stored for several months without any loss in its activity. All of the procedures were accomplished via mild reaction conditions and the products were afforded in high yields and short reaction times.
- Khosravi, Kaveh,Naserifar, Shirin
-
supporting information
p. 6584 - 6592
(2018/10/05)
-
- Synthesis of oxazolidin-2-ones and imidazolidin-2-ones directly from 1,3-diols or 3-amino alcohols using iodobenzene dichloride and sodium azide
-
A general and efficient method for the synthesis of oxazolidin-2-ones and imidazolidin-2-ones directly from 1,3-diols and 3-amino alcohols has been developed using the same reagent combination of iodobenzene dichloride (PhICl2) and sodium azide (NaN3).
- He, Tian,Gao, Wen-Chao,Wang, Wei-Kun,Zhang, Chi
-
supporting information
p. 1113 - 1118
(2014/04/03)
-
- Chemoselective, iron(ii)-catalyzed oxidation of a variety of secondary alcohols over primary alcohols utilizing H2O2 as the oxidant
-
A mild, iron-based catalyst system is presented that selectively oxidizes secondary alcohols to the corresponding hydroxy ketones in the presence of primary alcohols within 15 minutes at room temperature, utilizing H 2O2 as the oxidant.
- Lenze, Matthew,Bauer, Eike B.
-
p. 5889 - 5891
(2013/07/19)
-
- Catalyst-free selective oxidation of alcohols to carbonyls using trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane as an efficient oxidant
-
A simple and efficient method for the selective oxidation of alcohols to ketones using trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane at room temperature is developed. The reactions were smoothly proceeded under catalyst-free conditions to provide ketones in quantitative yields within short reaction times. Also, this method is compatible with many functional groups including aldehydes, olefins, halogens, amines and esters. Graphical Abstract: [Figure not available: see fulltext.]
- Azarifar, Davood,Najminejad, Zohreh,Khosravi, Kaveh
-
p. 979 - 983
(2013/09/23)
-
- Direct asymmetric aldol reactions inspired by two types of natural aldolases: Water-compatible organocatalysts and ZnII complexes
-
In this article the utility of water-compatible amino-acid-based catalysts was explored in the development of diastereo- and enantioselective direct aldol reactions of a broad range of substrates. Chiral C2-symmetrical proline- and valine-based
- Paradowska, Joanna,Pasternak, Monika,Gut, Bartosz,Gryzlo, Beata,Mlynarski, Jacek
-
scheme or table
p. 173 - 187
(2012/02/04)
-
- Lewis base catalysis by thiourea: N -bromosuccinimide-mediated oxidation of alcohols
-
In recent times, (thio)urea derivatives have become synonymous with hydrogen bonding owing to their extensive applicability as small molecule organocatalysts. In this paper, another activation mode by thiourea derivatives, namely via Lewis base catalysis, is disclosed for the NBS-mediated oxidation of alcohols. The mild reaction conditions employed here is suitable for chemoselective oxidation of secondary alcohol in the presence of primary alcohol.
- Tripathi, Chandra Bhushan,Mukherjee, Santanu
-
experimental part
p. 1592 - 1598
(2012/03/11)
-
- Direct asymmetric α-hydroxymethylation of ketones in homogeneous aqueous solvents
-
A chiral prolinamide-based zinc complex promotes the aldol reaction of ketones with aqueous formaldehyde, giving the corresponding adducts in good yields and high ees. The efficient direct aldol reaction of formaldehyde with ketones in homogeneous aqueous
- Pasternak, Monika,Paradowska, Joanna,Rogozińska, Maria,Mlynarski, Jacek
-
scheme or table
p. 4088 - 4090
(2010/08/19)
-
- PHENYL SUBSTITUTED CYCLOALKYLAMINES AS MONOAMINE REUPTAKE INHIBITORS
-
Phenyl-substituted cyclohexylamine derivatives and method for their synthesis and characterization are disclosed. Use of these compounds to treat/prevent neurological disorders as well as methods for their synthesis are set forth herein. Exemplary compoun
- -
-
Page/Page column 54
(2009/01/24)
-
- Highly efficient and selective oxidation of secondary alcohols to ketones under organic solvent and transition metal free conditions
-
The aqueous HBr/H2O2 was found to be highly efficient and green catalytic system for the selective oxidation of the secondary alcohols to ketones in excellent yields under organic solvent free conditions. The results of the oxidation of the secondary alcohols with solid alternatives of the aqueous hydrogen peroxide like SPC or SPB are also described.
- Jain, Suman L.,Sharma, Vishal B.,Sain, Bir
-
p. 6841 - 6847
(2007/10/03)
-
- IBX/n-Bu4NBr/CH2Cl2-H2O: A new mild system for selective oxidation of secondary alcohols
-
A new alternative system for the chemoselective oxidation of secondary hydroxyl group to ketone with IBX/n-Bu4NBr in CH2Cl 2-H2O has been developed. Under the reaction conditions, the secondary hydroxyl group was highly chemoselectively oxidized to the corresponding ketone, in moderate to good yields at rt, in the presence of primary hydroxyl group within the same molecule.
- Kuhakarn, Chutima,Kittigowittana, Krisada,Pohmakotr, Manat,Reutrakul, Vichai
-
p. 8995 - 9000
(2007/10/03)
-
- Design, Pharmacokinetic, and Pharmacodynamic Evaluation of a New Class of Soft Anticholinergics
-
Purpose. To design and evaluate a new class of soft anticholinergics with subtype selectivity. Methods. A new class of soft anticholinergics was designed based on the "inactive metabolite" approach. Four compounds were synthesized. The potency and soft na
- Huang, Fenglei,Browne, Clinton E.,Wu, Whei-Mei,Juhasz, Attila,Ji, Fubao,Bodor, Nicholas
-
p. 1681 - 1689
(2007/10/03)
-
- Cathodic cyclisation of N-(oxoalkyl)pyridinium salts - Formation of tricyclic indolizidine and quinolizidine derivatives in aqueous medium
-
The cathodic cyclisation of N-(oxoalkyl)pyridinium salts, derived from 4-methylpyridine and cyclic ketones, afforded functionalised tricyclic indolizidine and quinolizidine derivatives in high yields. Through systematic variation of the ring size of the k
- Heimann, Jens,Schaefer, Hans J.,Froehlich, Roland,Wibbeling, Birgit
-
p. 2919 - 2932
(2007/10/03)
-
- Aldol Synthesis with an Aqueous Solution of Formalin
-
With an aqueous solution of formalin, aldol reaction of trimethylsilyl enol ether proceeds moderately using tetrabutylammonium fluoride (TBAF). Furthermore, catalytic asymmetric hydroxymethylation with trimethoxysilyl enol ether using water tolerant (R)-B
- Ozasa, Nobuko,Wadamoto, Manabu,Ishihara, Kazuaki,Yamamoto, Hisashi
-
p. 2219 - 2221
(2007/10/03)
-
- Lewis base-promoted aldol reaction of dimethylsilyl enolates in aqueous dimethylformamide: Use of calcium chloride as a Lewis base catalyst
-
In the presence of CaCl2, dimethylsilyl (DMS) enolates smoothly reacted with aldehydes under mild conditions to give aldol adducts in good to high yields. The catalytic activities of various metal and tetrabutylammonium salts have revealed that CaCl2 works as a Lewis base catalyst to activate DMS enolates. The CaCl2-promoted reaction proceeded even in the presence of water or in pure water. This catalytic system was applicable to the aldol reaction with aqueous aldehydes such as formalin. Copyright
- Miura, Katsukiyo,Nakagawa, Takahiro,Hosomi, Akira
-
p. 536 - 537
(2007/10/03)
-
- Direct asymmetric α-hydroxylation of 2-hydroxymethyl ketones
-
A direct α-hydroxylation of racemic 2-hydroxymethyl ketones with the Sharpless epoxidation catalyst resulted in α,β-dihydroxy ketones in high ee (up to 97%) and in moderate to good isolated yield (up to 58%).
- Paju, Anne,Kanger, T?nis,Pehk, T?nis,Lopp, Margus
-
p. 7321 - 7326
(2007/10/03)
-
- Highly diastereoselective aldol synthesis from α-iodo ketones in aqueous media
-
Highly diastereoselective aldol synthesis from α-iodo ketones was promoted under aqueous conditions by a distannane system, (n-Bu3Sn)2, n-Bu2SnF2 and HMPA. Aqueous solutions of acetaldehyde, formaldehyde and piv
- Shibata, Ikuya,Kawasaki, Masatsugu,Yasuda, Makoto,Baba, Akio
-
p. 689 - 690
(2007/10/03)
-
- Preparation, Characterization, and Synthetic Uses of Lanthanide(III) Catalysts Supported on Ion Exchange Resins
-
Lanthanide(III) catalysts supported on ion exchange resins (Ln-resins) were prepared from Dowex, Amberlite, Amberlyst, and other cation exchange resins. The amount of lanthanides on resin supports was measured through EDTA titration. The results indicated that the lanthanides in aqueous solution exchanged with almost all the cations (H+ or Na+) on the resins to form stable ionic complexes between the lanthanides(III) and the resins. The effects of resin types, resin sizes, and lanthanide salts were investigated with a reaction of indole and hexanal in aqueous solution and with an aldol reaction of benzaldehyde and silyl enol ether in organic solvents. The study found that among ion exchange resins tested Amberlyst XN-1010 and Amberlyst 15 complexed with lanthanides(III) were the most effective catalysts. In addition, the selective Ln-resins were utilized to catalyze acetalization of aldehydes, aldol reaction of formaldehyde or benzaldehyde in aqueous solution, nucleophilic addition to an imine, allylation of an aldehyde, an aza Diels-Alder (DA) reaction, and a ring-opening reaction of an epoxide. Furthermore, glycosylation of alcohol using glucosyl fluoride as a donor was also promoted with the Ln-resin. Thus, this work demonstrated potential uses of lanthanide(III) catalysts supported on ion exchange resins in routine organic reactions.
- Yu, Libing,Chen, Depu,Li, Jun,Wang, Peng George
-
p. 3575 - 3581
(2007/10/03)
-
- Indium trichloride catalysed Mukaiyama aldol reaction in water
-
In the presence of a catalytic amount of indium(III) chloride (InCl3) (20 mol%), aldehydes react smoothly with ketone trimethylsilyl enol ethers in water to afford the corresponding aldol adducts in good yields.
- Loh, Teck-Peng,Pei, Jian,Cao, Guo-Qiang
-
p. 1819 - 1820
(2007/10/03)
-
- Rare Earth Metal Complexes as Water-Tolerant Lewis Acid Catalysts in Organic Synthesis
-
Rare earth metal triflates are stable in aqueous media and can act as Lewis acid catalysts in several carbon-carbon bond forming reactions. This article describes some of these reactions; aldol and Mannich-type reactions in aqueous solution, and Friedel-Crafts acylations and Fries rearrangement in organic solvents. The reactions proceeded smoothly in the presence of a catalytic amount of the triflate under mild conditions. Moreover, the catalysts could be recovered after the reactions were completed and could be reused.
- Kobayashi,Hashiya,Ishitani,Moriwaki,Nagayama
-
p. 193 - 202
(2007/10/03)
-
- Lanthanide Triflates as Water-Tolerant Lewis Acids. Activation of Commercial Formaldehyde Solution and Use in the Aldol Reaction of Silyl Enol Ethers with Aldehydes in Aqueous Media
-
Lanthanide trifluoromethanesulfonates (triflates), especially ytterbium triflate (Yb(OTf)3), were found to be stable Lewis acids in water.In the presence of a catalytic amount of lanthanide triflate, formaldehyde in water solution (commercial formaldehyde
- Kobayashi, Shu,Hachiya, Iwao
-
p. 3590 - 3596
(2007/10/02)
-
- Expeditious and Efficient Annulation Protocol for the Synthesis of α,β-Unsaturated δ-Lactones from β-Keto Esters
-
β-Keto esters 6a-e are transformed into β-keto alcohols 7a-e, which are homologated to phosphonates 9a-e.Intramolecular Horner-Wadsworth-Emmons reaction affords δ-lactones 10a-d in excellent overall yields. Key words: δ-Lactones; β-Keto esters; Intramolecular; Phosphonates; Horner-Wadsworth-Emmons
- Nangia, A.,Rao, P. Bheema
-
p. 2375 - 2378
(2007/10/02)
-
- Fluoromethylated and hydroxymethylated derivatives of N-methyl-D-aspartate receptor antagonist 1-[1-(2-thienyl)cyclohexyl]piperidine
-
Derivatives with fluoromethyl and hydroxymethyl groups on the cyclohexyl ring of 1-[1-(-2-thienyl)cyclohexyl]piperidine (TCP), a noncompetitive antagonist of N-methyl-D-aspartate (NMDA) receptor, were tested in a radioligand binding assay to evaluate thei
- Tsukiyama,Hashimoto,Katayama,Nishikawa,Tobe,Maeda
-
p. 1581 - 1584
(2007/10/02)
-
- Lanthanide Trifluoromethanesulfonates as Stable Lewis Acids in Aqueous Media. Yb(OTf)3 Catalyzed Hydroxymethylation Reaction of Silyl Enol Ethers with Commercial Formaldehyde Solution
-
Silyl enol ethers smoothly react with commercial formaldehyde solution to give the corresponding hydroxymethylated adducts in high yields by the promotion of a catalytic amount of ytterbium(III) triflate (Yb(OTf)3), which is a stable Lewis acid in aqueous
- Kobayashi, Shu
-
p. 2187 - 2190
(2007/10/02)
-
- Efficient synthesis of α-(hydroxymethyl) ketones not available through aldol-type processes
-
An efficient synthesis of α-(hydroxymethyl) ketones from β-keto esters has been developed, which is experimentally simple, amenable to large scale production and provides products of high purity without resort to chromatography in most cases. The method is a useful alternative and complement to condensation processes.
- Hitchcock,Perron,Martin,Albizati
-
p. 1059 - 1061
(2007/10/02)
-
- WATER-PROMOTED ORGANIC REACTIONS. ALDOL REACTION OF SILYL ENOL ETHERS WITH CARBONYL COMPOUNDS UNDER ATMOSPHERIC PRESSURE AND NEUTRAL CONDITIONS.
-
As a consequence of the hydrophobic effect, the reaction between silyl enol ethers and aldehydes are shown to proceed without a catalyst in aqueous solution and neutral conditions providing crossed-aldol products with a syn selectivity, as under pressure, that is the reverse in comparison with the acid catalysed reaction.With α,β-unsaturated aldehydes, 1,2- and 1,4-addition were observed, whereas with α,β-unsaturated ketones, only 1,4-addition occured.
- Lubineau, Andre,Meyer, Elsa
-
p. 6065 - 6070
(2007/10/02)
-
- Chemoselective reduction of β-keto-esters to β-keto-alcohols
-
Chemoselective reduction of the ester group in keto-esters was studied.Treatment of potassium (or lithium) enolate anions of β-keto-esters with aluminium hydride reduced the ester group chemoselectvely to give β-keto-alcohols in moderate yield.Similar reactions of γ- and δ-keto-esters were not chemoselective, yielding a mixture of the diol and the keto-alcohol.Keywords - chemoselective reduction; aluminium hydride; β-keto-ester; β-keto-alcohol; potassium hydride; enolate anion.
- Isobe, Kimiaki,Mohri, Kunihiko,Sano, Hiromichi,Taga, Juni-ichi,Tsuda, Yoshisuke
-
p. 3029 - 3032
(2007/10/02)
-
- FURTHER STUDIES ON THE UTILITY OF SODIUM HYPOCHLORITE IN ORGANIC SYNTHESIS. SELECTIVE OXIDATION OF DIOLS AND DIRECT CONVERSION OF ALDEHYDES TO ESTERS
-
Sodium hypochlorite in acetic acid solution selectively oxidizes secondary alcohols to ketones in the presence of primary alcohols and converts aldehydes to methyl esters in the added presence of methanol.
- Stevens, Robert V.,Chapman, Kevin T.,Stubbs, Cheryl A.,Tam, Weyton W.,Albizati, Kim F.
-
p. 4647 - 4650
(2007/10/02)
-
- Thermally induced crossed aldol condensations
-
A relatively efficient, noncatalytic method for effecting crossed aldol condensations between cyclic ketones and aldehydes and between cyclic 1,3-diones and methyl vinyl ketone is reported.
- Findlay, John A.,Desai, Dixit N.,Macaulay, John B.
-
p. 3303 - 3304
(2007/10/02)
-