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TBAH-Catalyzed One-Pot Synthesis of Symmetrical Trithiocarbonates from Alkyl Halides and Carbon Disulfide under Neat Aqueous ConditionsEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217132AbstractA novel and efficient, tetra--butylammonium hydroxide catalyzed, one-pot protocol has been developed for the synthesis of symmetrical trithiocarbonates from alkyl halides and carbon disulfide under neat aqueous conditions.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 21, 2009 Category: Chemistry Tags: short paper Source Type: journals

p-Quinols and p-Quinol Ethers from 2,4,6-TrialkylphenolsEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217127AbstractThe oxidation of 2,4,6-trialkylphenols with lead(IV) oxide and 70% perchloric acid in water-acetone or in alcohols gives -quinols or -quinol ethers, respectively. Some nonmetallic oxidants serve the same purpose.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 21, 2009 Category: Chemistry Tags: short paper Source Type: journals

Dess-Martin Periodinane Mediated Intramolecular Cyclization of Phenolic Azomethines: A Solution-Phase Strategy toward Benzoxazoles and BenzothiazolesEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217136AbstractDess-Martin periodinane (DMP), a highly versatile hypervalent iodine(V) reagent, was found to efficiently mediate the intramolecular cyclization of phenolic azomethines/Schiff bases at ambient temperature leading to the rapid and expeditious synthesis of substituted benzoxazoles and benzothiazoles. Furthermore, a solution-phase strategy has been developed by treating the reaction mixtures sequentially with Amberlyst A-26 thiosulfate resin and diisopropylaminomethyl resin (PS-DIEA), which remove excess reagent and byproducts, to give pure products. [...]© Georg Thieme Verlag Stut...
Source: Synthesis - November 21, 2009 Category: Chemistry Tags: short paper Source Type: journals

Enantioselective Organocatalytic Diels-Alder ReactionsEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217130AbstractEnantioselective organocatalytic asymmetric Diels-Alder reactions provide a facile and efficient route to optically active functionalized cyclohexenes, which can be further transformed into a variety of important organic compounds. A variety of small organic molecules such as prolines, imidazolidinones, chiral Brønsted acids, guanidines, carbenes and alkaloids can be used as different catalyst systems to induce enantioselectivity in the reaction. This review provides an overview of the history of the asymmetric organocatalyzed Diels-Alder reaction.[...]© Georg Thieme Verlag...
Source: Synthesis - November 21, 2009 Category: Chemistry Tags: review Source Type: journals

Direct Conversion of Carbon-Hydrogen into Carbon-Carbon Bonds by First-Row Transition-Metal CatalysisEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217131AbstractThis review summarizes first-row transition-metal catalysis for the conversion of carbon-hydrogen into carbon-carbon bonds. In particular, catalysis by manganese, iron, cobalt, copper, and nickel is covered. These metals are abundant in the Earth’s crust but so far they have been comparatively underutilized in carbon-hydrogen bond-functionalization reactions.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 21, 2009 Category: Chemistry Tags: review Source Type: journals

Mild and High-Yielding Synthesis of β-Keto Esters and β-KetoamidesEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217135AbstractIn the presence of sodium acetate, the reaction between 2,2,6-trimethyl-4-1,3-dioxin-4-one and secondary or tertiary alcohols (including chiral ones) or primary or secondary amines could be carried out in refluxing tetrahydrofuran, under much milder conditions than those described in the literature. In these new conditions, side products normally observed using the traditional protocol were avoided, and β-keto esters and β-ketoamides were normally obtained in quantitative yields.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | �...
Source: Synthesis - November 21, 2009 Category: Chemistry Tags: practical synthetic procedures Source Type: journals

Large-Scale Preparation of Polyfunctional Benzylic Zinc Reagents by Direct Insertion of Zinc Dust into Benzylic Chlorides in the Presence of Lithium ChlorideEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217134AbstractHighly functionalized benzylic zinc chlorides are prepared by the direct insertion of commercially available zinc dust into the corresponding benzylic chlorides in the presence of stoichiometric amount of lithium chloride. These polyfunctional zinc organometallics react with various electrophiles leading to a broad range of functionalized products.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 21, 2009 Category: Chemistry Tags: practical synthetic procedures Source Type: journals

An Alternative to Pictet-Gams Reaction Triggered by Hendrickson Reagent: Isoquinolines and β-Carbolines from AmidesEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217138AbstractThe Hendrickson reagent derived from triflic anhydride and triphenylphosphine oxide exhibited high oxophilicity and induced the intramolecular cyclization of β-arylethylamides perfectly. Thus, a one-pot protocol to access isoquinoline and β-carboline was developed involving cyclization followed by oxidative aromatization.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 21, 2009 Category: Chemistry Tags: paper Source Type: journals

Facile [2+2] Cycloaddition of DDQ to an Alkyne: Synthesis of Pyrrolyl- and Indolylbicyclo[4.2.0]octadienes from C-Ethynylpyrroles or C-EthynylindolesEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217133Abstract-Ethynylpyrroles or -indoles, which can be prepared by cross-coupling of pyrroles or indoles with haloalkynes on active surfaces, undergo [2+2]-cycloaddition reactions with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to give 2-pyrrolyl- or 3-indolylbicyclooctadienes in almost quantitative yields. The adducts are charge-transfer complexes that are paramagnetic in the solid state, and therefore represent a new family of densely functionalized pyrrole and indole derivatives potentially useful as pharmaceutical candidates, highly potent building blocks, or precursors of advanced materi...
Source: Synthesis - November 21, 2009 Category: Chemistry Tags: paper Source Type: journals

Synthesis of 5-Amino-1,10b-dihydro-2H-chromeno[3,4-c]pyridine-2,4(3H)-diones from Coumarins and Cyanoacetamides under Basic ConditionsEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217128AbstractThe reaction of various coumarins with cyanoacetamide derivatives under basic conditions (sodium ethoxide, piperidine or 2,2,6,6-tetramethylpiperidine), proceeds via an interesting process which involves skeletal rearrangement of the coumarin, a Michael addition and two cyclizations to afford 5-amino-1,10b-dihydro-2-chromeno[3,4-]pyridine-2,4(3)-diones. The same reaction in the presence of ,¢-ethane-1,2-diylbis(2-cyanoacetamide) gives the corresponding mono and bis 5-amino-1,10b-dihydro-2-chromeno[3,4-]pyridine-2,4(3)-diones.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkG...
Source: Synthesis - November 21, 2009 Category: Chemistry Tags: paper Source Type: journals

An Approach to Azabicyclo[n.3.1]alkanes by Double Mannich ReactionEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217137AbstractChlorotrimethylsilane-promoted double Mannich annulation of ketones using ,-bis(methoxymethyl)benzylamine has been explored. It has been shown that the structure of the substrate drastically influenced the outcome of the reaction. The method allows azabicyclo[.3.1]alkane derivatives ( = 2-5) to be obtained in good yields.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 21, 2009 Category: Chemistry Tags: paper Source Type: journals

A Convenient Two-Step Synthesis of 2-ArylbenzofuransEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217129AbstractA novel and convenient two-step synthesis of 2-arylbenzofurans is described which proceeds via a selective cross-pinacol-type coupling between a salicylaldehyde and an aromatic aldehyde, followed by an acid-promoted cyclization. One advantage of this method is that separation of the three possible pinacol products that can form during the cross-coupling is not necessary. This method is also applied to the synthesis of the 2-arylbenzofuran-containing natural product, homoegonol.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract �...
Source: Synthesis - November 21, 2009 Category: Chemistry Tags: paper Source Type: journals

Asymmetric Synthesis of All Stereoisomers of α-Methylthreonine Using an Organocatalytic Steglich Rearrangement Reaction as a Key StepEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217140AbstractAn efficient synthetic route to all four stereoisomers of α-methylthreonine has been established. Each type of stereoisomer has been isolated in diastereomerically pure form and with an enantiomeric excess of at least 86% ee. The key step in this multi-step synthesis is an enantioselective organocatalytic Steglich rearrangement reaction of O-acetylated azlactones. The Steglich rearrangement was also extended to other substrates.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 21, 2009 Category: Chemistry Tags: paper Source Type: journals

Synthesis of β-Arylporphyrins and Oligophenylenediporphyrins by the Suzuki-Miyaura ReactionEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217114AbstractSeveral β-aryl-substituted porphyrins were prepared in good yields by Suzuki-Miyaura cross-coupling of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,10,15,20-tetraphenylporphinatozinc(II) with various aryl bromides. Additionally, syntheses of β,β′-diporphyrins linked by biphenylene or quaterphenylene units were examined.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 21, 2009 Category: Chemistry Tags: paper Source Type: journals

Simple and Efficient Procedure for a Multigram Synthesis of Both trans- and cis-1-Amino-2-(trifluoromethyl)cyclopropane-1-carboxylic AcidEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217141AbstractA simple and efficient procedure for the multigram synthesis of both (±)-- and (±)--1-amino-2-(trifluoromethyl)cyclopropane-1-carboxylic acid was developed. The key step of the synthesis is the addition of 1-diazo-2,2,2-trifluoroethane to methyl 2-[(-butoxycarbonyl)amino]acrylate, followed by thermal decomposition of the resulting pyrazoline. Gram quantities of - and -1-amino-2-(trifluoromethyl)cyclopropane-1-carboxylic acid were easily prepared from -serine in one synthetic run.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstrac...
Source: Synthesis - November 21, 2009 Category: Chemistry Tags: paper Source Type: journals

Ring Enlargement of Carbohydrate-Derived 1,2-Oxazines to Enantiopure 5-Bromo-1,2-oxazepines and Subsequent Palladium-Catalyzed ReactionsEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217126AbstractDibromocarbene addition to -glyceraldehyde-derived 1,2oxazines and provided dibromocyclopropane intermediates - and -, which smoothly reacted with methanol under ring enlargement to furnish 5-bromo-1,2oxazepine derivatives and . Related 1,2-oxazines such as arabinose-derived compounds furnished the 1,2-oxazepine derivatives - and -with fair efficacy. The alkenyl bromide moiety of 1,2-oxazepine derivatives and was then exploited for the introduction of new substituents via palladium-catalyzed C-C bond forming processes (Sonogashira, Suzuki, Stille, and Heck reactions). These tra...
Source: Synthesis - November 21, 2009 Category: Chemistry Tags: paper Source Type: journals

Heck Reaction in Diols and Cascade Formation of Cyclic KetalsEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217139AbstractThe regioselective Heckarylation of butyl vinyl ether in alcohols is utilized for the formation of a variety of cyclic ketals. When carried out in ethylene glycol, propane-1,2-diol, or propane-1,3-diol, the palladium-catalyzed arylation afforded dioxolanes or dioxanes directly. With diols such as glycerol, 3-chloropropane-1,2-diol, and 2-methylpropane-1,3-diol, isolation of the Heck adducts and the use of an acid catalyst for the ketalization were necessary; an efficient phosphoric acid was identified. The procedure presented provides a new pathway for the synthesis of cyclic ket...
Source: Synthesis - November 21, 2009 Category: Chemistry Tags: feature article Source Type: journals

A Direct Synthesis of Racemic 1,3,4,5-TetragalloylapiitolEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217123AbstractA direct and flexible synthesis of racemic 1,3,4,5-tetragalloylapiitol is described.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 14, 2009 Category: Chemistry Tags: short paper Source Type: journals

A Practical Synthesis of 1-N-SEM-Protected 3-Iodo-7-methyl-2-piperidin-3-ylindoleEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217110AbstractA convenient procedure for the preparation of the 1-N-SEM-protected 3-iodo-7-methyl-2-piperidin-3-ylindole is described. This scaffold provides access to unique and diverse 7-methyl-substituted indole libraries.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 14, 2009 Category: Chemistry Tags: practical synthetic procedures Source Type: journals

Regioselective Hydrogenation of α,β-Unsaturated Ketones over Wilkinson’s CatalystEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217117AbstractThe reactivity of a variety of α,β-unsaturated acyclic and cyclic ketones towards regioselective hydrogenation in the presence of Wilkinson’s catalyst was determined. Hydrogenation of sterically hindered α,β-unsaturated ketones proceeded at inefficient rates, if at all.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 14, 2009 Category: Chemistry Tags: paper Source Type: journals

Synthetic Aromatic Amino Acids from a Negishi Cross-Coupling ReactionEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217124AbstractAn N,O-protected, iodinated bishomoalanine derivative, safely available from glutamic acid, reacts with aryl halides in a Negishi reaction in high yields. From the coupling product, Fmoc-protected amino acids with aromatic and heteroaromatic side chains were generated in high yields by racemization-free procedures. These monomers could be used for solid-phase peptide synthesis.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 14, 2009 Category: Chemistry Tags: paper Source Type: journals

Reductive Dehalogenation of Aryl Bromides and Chlorides and Their Use as Aryl Blocking GroupsEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217112AbstractBromo and chloro substituents serve as excellent blocking groups on aromatic rings. When a halo substituent is to an -directing group, the ortho positions can be easily functionalized, and the halo group can be subsequently removed by catalytic hydrogenation under neutral conditions. As expected, bromides are reduced more quickly than chlorides and the reaction requires the use of less catalyst. Bromides can be selectively reduced in the presence of nitro, chloro, cyano, keto, or carboxylic acid groups. [...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of c...
Source: Synthesis - November 14, 2009 Category: Chemistry Tags: paper Source Type: journals

One-Pot Condensation-Oxidation of Glyoxamide with 1,2-Diamines Providing Imidazolines and BenzimidazolesEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217120AbstractA novel method for the preparation of imidazolines and benzimidazoles bearing an amide at the 2-position, is described. The reactions of the glyoxamide with aliphatic and aromatic 1,2-diamines were found to form five-membered imidazolines and benzimidazoles by a one-pot condensation-oxidation procedure.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 14, 2009 Category: Chemistry Tags: paper Source Type: journals

A Traceless, Solid-Supported Synthesis of β-Turn Mimetics Based on the Hexahydropyrazino[1,2-a]pyrazine-1,2-dione ScaffoldEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217125AbstractThe solid-supported synthesis of a library of β-turn mimetics based on the three-component Petasis condensation and 2,5-diketopiperazine formation is reported. The eight-step sequence starts from optically pure ()-piperazine-2-carboxylic acid dihydrochloride, which is first converted into an orthogonally protected, resin-bound amino derivative. The subsequent transformations lead to compounds having the common hexahydropyrazino[1,2-]pyrazine-1,2-dione core and diverse side chains, which mimic the β-turn structure. This synthetic route includes protection of the initial ...
Source: Synthesis - November 14, 2009 Category: Chemistry Tags: paper Source Type: journals

A Facile Chiral Pool Synthesis of (S)-6-Nitroindoline-2-carboxylic Acid from l-PhenylalanineEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217122Abstract()-6-Nitroindoline-2-carboxylic acid, a substructure occurring in numerous biologically active natural products, was synthesized with moderate yield (53%) and high enantiomeric excess (>99.5%) starting from the nitration of -phenylalanine, which is a commercially available chiral pool compound, followed by successively bromination and intramolecular cyclization. The route was carried out in gram quantities and it is suitable for industrial application due to its convenient reaction conditions and low cost.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table...
Source: Synthesis - November 14, 2009 Category: Chemistry Tags: paper Source Type: journals

Single-Step Conversion of Electron-Deficient Aldehydes into the Corresponding Esters in Aqueous Alcohols in the Presence of Iodine and Sodium NitriteEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217121AbstractThe direct conversion of aldehydes into their corresponding esters in the presence of iodine and sodium nitrite in aqueous alcohols is reported. In all these reactions, alcohol serves as reactant and also as reaction medium. Almost quantitative yields were obtained with aldehydes containing electron-withdrawing substituents and heterocyclic aldehydes.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 14, 2009 Category: Chemistry Tags: paper Source Type: journals

Efficient One-Pot Synthesis of Spirooxindole Derivatives by Ethylenediamine Diacetate Catalyzed Reactions in WaterEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217116AbstractA simple and efficient one-pot synthetic approach was used for the preparation of biologically interesting spirooxindole derivatives by means of three-component reactions of isatins, malononitrile, and 1,3-dicarbonyl compounds catalyzed by ethylenediamine diacetate (EDDA) in an aqueous medium. This method is of great value because of its environmentally benign character, high yield, and easy handling.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 14, 2009 Category: Chemistry Tags: paper Source Type: journals

Radical Conjugate Addition of Aryl-Tethered β-Alkoxyacrylates: Formal Synthesis of (±)-Frenolicin B and (±)-epi-Frenolicin BEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217118AbstractThe radical conjugate addition of aromatic-tethered -stannyl ketyl radicals to β-alkoxyacrylates is demonstrated for the preparation of benzopyran-γ-lactone-fused tricyclic systems. This method is then applied to the stereodivergent formal synthesis of the kinase inhibitor (±)-frenolicin B and (±)--frenolicin B.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 14, 2009 Category: Chemistry Tags: paper Source Type: journals

Pd/C and NaBH4 in Basic Aqueous Alcohol: An Efficient System for an Environmentally Benign Oxidation of AlcoholsEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
We report the oxidation of a wide range of alcohols using an environmentally benign and economical process. The use of Pd/C heterogeneous catalysts along with NaBHin aqueous ethanol or methanol and either KCO or KOH as base at room temperature under molecular oxygen or air give the corresponding oxidation products. This protocol is versatile since it is capable of oxidizing alcohols to its desired carbonyl or carboxyl counterpart. Room temperature reaction in aqueous system and recyclability of the catalyst are among the advantages of this manipulation. These advantages make the process safe and cheaper rendering it favora...
Source: Synthesis - November 14, 2009 Category: Chemistry Tags: paper Source Type: journals

Regioselective, One-Pot Syntheses of Symmetrically and Unsymmetrically Halogenated 2′,6′-BispyrazolylpyridinesEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
Synthesis 2009; 2009: e9-e9DOI: 10.1055/s-0029-1217119© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | FREE: Full text (Source: Synthesis)
Source: Synthesis - November 13, 2009 Category: Chemistry Tags: addenda and errata Source Type: journals

Synform issue 2009/9Email this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
Synthesis 2009; 2009: A76-A85DOI: 10.1055/s-0029-1218257© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparati...
Source: Synthesis - November 13, 2009 Category: Chemistry Tags: synform Source Type: journals

A Practical Method for O-Acylation of N-Hydroxythiazole-2(3H)-thionesEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217102AbstractO-Acylation of 4- and 4,5-substituted -hydroxythiazole-2(3)-thiones occurred in solutions of acetone upon treatment with solid KCO and a variety of neat acyl chlorides (primary, secondary, and tertiary alkyl, aryl; 60-87% yield; ∼10 g scale).[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 7, 2009 Category: Chemistry Tags: practical synthetic procedures Source Type: journals

Synthesis of 1,4-Disubstituted 1,2,3-Triazoles by Use of Copper(I) and Amino Acids Ionic Liquid Catalytic SystemEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217111AbstractAn efficient and green one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from aryl iodides and alkyl chlorides, sodium azide, and terminal alkynes catalyzed by copper(I) and amino acid ionic liquid (AAIL) in [BMIM]BF was developed. The reactions proceeded smoothly to generate the corresponding products in high yields. In addition, CuI, AAIL, and [BMIM]BF could be recovered for six consecutive trials without significant loss of activity.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 7, 2009 Category: Chemistry Tags: paper Source Type: journals

An Expeditious Method for the Preparation of 2-Hydroxy-1,4-dioxane and Its Use in Reductive Alkylation of AminesEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217101AbstractSelective oxidation of diethylene glycol by a ruthenium(VIII) species, obtained in situ from ruthenium(III) chloride-sodium periodate in the presence of a catalytic quantity of water, affords a monoaldehyde in the form of the internal acetal 2-hydroxy-1,4-dioxane. This compound was used in reductive alkylations of selected primary and secondary amines, demonstrating its utility in the preparation of target structures with the 2-(2-hydroxyethoxy)ethylamino unit.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 7, 2009 Category: Chemistry Tags: paper Source Type: journals

Practical Synthesis of α-Perfluoroalkyl Cyclic Imines and AminesEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217104AbstractA convenient and simple approach for the preparation of α-CFand α-CF substituted pyrrolines, tetrahydropyridines, tetrahydroazepine is described. Claisen condensation of N-protected cyclic amides with esters of perfluorocarboxylic acids followed by deprotection and decarboxylation in acidic media leads to the desired products. Reduction of these imines permits to obtain 5-, 6-, and 7-membered cyclic amines with α-CFor α-CF group in good to moderate overall yields.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstr...
Source: Synthesis - November 7, 2009 Category: Chemistry Tags: paper Source Type: journals

Simple and Convenient Method for the Synthesis of 2-Substituted Glutaconaldehyde Salts and 2-Substituted Glutaconaldehyde DerivativesEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217105AbstractConvenient and scalable syntheses of 2-substituted glutaconaldehyde salts were accomplished from the corresponding pyridinium salts. Glutaconaldehyde salts were additionally converted into aminopentadienal derivatives.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 7, 2009 Category: Chemistry Tags: paper Source Type: journals

Intramolecular 1,3-Dipolar Cycloaddition of Alkenylnitrones of the 4H-Imidazole Series: Synthesis of a New Nitroxide pH-Sensitive Spin ProbeEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217109AbstractA new method was used for the preparation of a pH-sensitive spin probe involving an intramolecular 1,3-dipolar cycloaddition - reductive isoxazolidine ring-opening - oxidation reaction sequence. 2-(2-Allyloxyphenyl)-5-R-4,4-dimethyl-4-imidazole-3-oxides (R = Me, NMe), prepared from 3-hydroxylamino-3-methylbutan-2-one, undergo intramolecular 1,3-dipolar cycloaddition upon heating in toluene. Treatment of the cycloadducts with low-valence titanium (LVT) reagent resulted in reductive cleavage of the N-O bond of the isoxazolidine ring to give 3′-hydroxymethyl-5,5-di...
Source: Synthesis - November 7, 2009 Category: Chemistry Tags: paper Source Type: journals

An Expedient Three-Component Synthesis of Tertiary BenzylaminesEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217108AbstractA Mannich-like zinc-mediated three-component reaction of aromatic halides, amines, and paraformaldehyde is described. This procedure, which involves the in situ formation of arylzinc reagents, allows the straightforward synthesis of a range of functionalized tertiary benzylamines.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 7, 2009 Category: Chemistry Tags: paper Source Type: journals

Diethyl [Nitro(diazo)methyl]phosphonate: Synthesis and Reactivity towards AlkenesEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217103AbstractA novel and convenient synthesis of diethyl [nitro(diazo)methyl]phosphonate and its reactions with various alkenes are described. The reactivity of diethyl [nitro(diazo)methyl]phosphonate is shown to be dependent on the structure of the alkene. A number of cyclopropyl α-nitrophosphonates were obtained.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 7, 2009 Category: Chemistry Tags: paper Source Type: journals

Total Synthesis of (±)-Petasitolone and (±)-FukinoneEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
Synthesis 2009; 2009: e8-e8DOI: 10.1055/s-0029-1217106© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | FREE: Full text (Source: Synthesis)
Source: Synthesis - November 6, 2009 Category: Chemistry Tags: addenda and errata Source Type: journals

Paternò-Büchi Reactions of Silyl Enol Ethers and EnamidesEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217095Abstract3-(Silyloxy)oxetanes are obtained by irradiating mixtures of aromatic aldehydes and silyl enol ethers in benzene as the solvent. The reactions occur with high simple diastereoselectivity and, when R is chiral, with high facial diastereoselectivity. Under similar conditions, but in acetonitrile rather than benzene as the preferred solvent, the Paternò-Büchi reaction of -acyl enamines (enamides) gives the corresponding protected 3-aminooxetanes. The -products are obtained with significant simple diastereoselectivity.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connect...
Source: Synthesis - November 4, 2009 Category: Chemistry Tags: practical synthetic procedures Source Type: journals

Synthesis of Racemic and Enantiomerically Pure Acetylenic ω-Keto Esters Derived from 2-Methyl-1,3-cycloalkanediones and 2-Methylcycloalkanones RespectivelyEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217043AbstractRacemic and enantiomerically pure alkynyl esters tethered, respectively, to 2-methyl-1,3-cycloalkanediones and 2-methylcycloalkanones were readily obtained starting from common intermediates, which were available on large scale.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 4, 2009 Category: Chemistry Tags: practical synthetic procedures Source Type: journals

An Improved Procedure for the Preparation of [Bis(2,2,2-trifluoroethyl)phosphono]acetic AcidEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217086AbstractA different and improved procedure for the preparation of [bis(2,2,2-trifluoroethyl)phosphono]acetic acid in just one step from bis(2,2,2-trifluoroethyl) phosphonate is described. The protocol employs a Michaelis-Becker reaction between commercially available bis(2,2,2-trifluoroethyl) phosphonate and bromoacetic acid, furnishing [bis(2,2,2-trifluoroethyl)phosphono]acetic acid in 50-54% yield.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 4, 2009 Category: Chemistry Tags: practical synthetic procedures Source Type: journals

Michael Addition-Lactonization Reaction of Electron-Deficient Alkynes with N-(Diphenylmethylene)glycinates: An Efficient Synthesis of 3-Amino-2-pyrone DerivativesEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217098AbstractA mild and efficient process for the synthesis of 3-amino-2-pyrone derivatives has been developed. This approach is based on the Michael addition of -(diphenylmethylene)glycinates to various alkynyl ketones, followed by lactonization using 10 mol% sodium hydroxide as catalyst. Aromatic and aliphatic alkynyl ketones were converted into the corresponding 3-amino-2-pyrone derivatives in moderate to high yields. When methyl propiolate was submitted to the reaction, α,β-dehydroamino acids were formed in good yields.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet con...
Source: Synthesis - November 4, 2009 Category: Chemistry Tags: paper Source Type: journals

Palladium-Catalyzed One-Pot Synthesis of 4-Aryl-1H-1,2,3-triazoles from anti-3-Aryl-2,3-dibromopropanoic Acids and Sodium AzideEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217097Abstract4-Aryl-1-1,2,3-triazoles were synthesized from 3-aryl-2,3-dibromopropanoic acids and sodium azide by a one-pot method using ,-dimethylformamide as solvent in the presence of tris(dibenzylideneacetone)dipalladium(0) [Pd(dba)] and Xantphos.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 4, 2009 Category: Chemistry Tags: paper Source Type: journals

Expedient Reductive Amination of Aldehyde Bisulfite AdductsEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217050AbstractA novel, one-pot protocol for the direct reductive amination of aldehyde bisulfite adducts is reported. Bisulfite adducts of aliphatic and aromatic aldehydes, on treatment with an organic base under non-aqueous conditions liberate the aldehyde in situ, which then undergoes efficient reductive amination with amines in the presence of sodium triacetoxyborohydride.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 4, 2009 Category: Chemistry Tags: paper Source Type: journals

Total Synthesis of gem-Difluoromethylenated Analogues of PironetinEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217099AbstractThe straightforward synthesis of four -difluoromethylenated analogues of pironetin is described. Our synthesis features the efficient construction of the key intermediates through the indium-mediated -difluoropropargylation of aldehydes with the fluorine-containing building block.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 4, 2009 Category: Chemistry Tags: paper Source Type: journals

[5+3] Cycloaddition of 3-Oxidopyrylium: A Novel Route to Functionalized Cyclooctanoids from FuransEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
We report a facile and efficient synthesis of highly functionalized cyclooctanoid derivatives by employing a dimerization reaction of 3-oxidopyrylium ylides. Different substituents are introduced on the dimer and the stereochemical outcome of the resultant cyclooctanoids is unambiguously established by single-crystal X-ray analysis.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 4, 2009 Category: Chemistry Tags: paper Source Type: journals

Stereoselective Synthesis and Biological Studies of the C2 and C3 Epimer and the Enantiomer of Pachastrissamine (Jaspine B)Email this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217096AbstractThe synthesis of the C2 and C3 epimer and also the enantiomer of jaspine B from -glucose is reported. The cytotoxicity of these isomers along with jaspine B and its C2 epimer on MCF7 cells has been correlated with commercially available anticancer drug Epirubicin.[...]© Georg Thieme Verlag Stuttgart ˙ New YorkGet connected:Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - November 4, 2009 Category: Chemistry Tags: paper Source Type: journals

A Convenient Synthesis of New Types of Benzodiazepine Derivatives: 2-Alkylsulfanyl-3H-4,5-dihydro-1,3-benzodiazepin-4-ones and 2-Alkylsulfanyl-3H-4,5-dihydro-1,3-benzodiazepine-4-thionesEmail this article to a colleague. Save this article to My Clippings. Discuss or comment on this article.
SynthesisDOI: 10.1055/s-0029-1217100AbstractAn efficient method for preparing 2-alkylsulfanyl-3-4,5-dihydro-1,3-benzodiazepin-4-ones and 2-alkylsulfanyl-3-4,5-dihydro-1,3-benzodiazepine-4-thiones under mild conditions has been developed. Thus, 2-(2-isocyanophenyl)acetamides and 2-(2-isocyanophenyl)thioacetamides, easily available from respective 1-isocyano-2-methylbenzenes, were converted into the corresponding isothiocyanates on treatment with sulfur in the presence of a catalytic amount of selenium, which were then reacted with an equimolar amount to sodium hydride to give 2-(sodiosulfanyl)-3-4,5-dihydro-1,3-benzodiazepi...
Source: Synthesis - November 4, 2009 Category: Chemistry Tags: paper Source Type: journals