PEG-OSO3H as an efficient and recyclable catalyst for the synthesis of β-amino carbonyl compounds via the Mannich reaction in PEG-H2O

Sulfuric acid-modified polyethylene glycol 6000（PEG-OSO₃H） was applied as an efficient and recyclable catalyst for the synthesis ofβ-amino carbonyl compounds via the Mannich reaction between aldehydes,aromatic ketones and aromatic amines at room temperature using PEG400-H₂O（1:1） as environment-friendly solvents.The reactions were completed in short times and mild reaction conditions with good to excellent yields.     

Efficient Lewis Acids Catalyzed Aza-Michael Reactions of Enones with Carbamates

The β-amino carbonyl functionality is not only a segment of biologically important natural products but also a versatile intermediate for the synthesis of nitrogen-containing compounds.1 The development of novel synthetic methods leading to β-amino ketone, β-amino acids or their derivatives has attracted much attention in organic synthesis.2 Among the traditional methods for generating β-amino carbonyl compounds, Mannich-type reaction is one of the classical and powerful methods.3 However,…     

Facile Aldol Reaction Between Unmodified Aldehydes and Ketones in Bronsted Acid Ionic Liquids

A series of condensation reactions of unmodified ketones and aromatic aldehydes to prepare α,β-unsaturated carbonyl compounds by means of Aldol reactions in Bronsted acid ionic liquids(BAILs)was explored.1-Butyl-3-methylimidazolium hydrogen sulphate(BMImHSO4)acting as an effective media and catalyst in aldol reactions was compared with other BAILs,with the advantages of high conversion and selectivity.The product was easily isolated and the left ionic liquid can be readily recovered and reused at least 3 times with almost the same efficiency.The scope and limitation of the present method were explored and the possible catalytic mechanism was speculated.     

Sulfonated poly(4-vinylpyridine) heteropolyacid salts:A reusable green solid catalyst for Mannich reaction

Sulfonated poly（4-vinylpyridine） heteropolyacid salts acted as a heterogeneous catalyst to effectively catalyze the one-pot synthesis of β-amino carbonyl compounds via the Mannich reaction between aromatic aldehydes, aromatic ketone, and aromatic amines. In addition, the catalyst could be easily recovered by the filtration and reused six times without significant loss of catalytic activity.     

Coupling Reaction of Carbonyl Compounds Mediated by Gallium Metal in Aqueous Media

A simple and effective pinacol coupling of various aromatic aldehydes mediated by gallium in good yields has been carried out. The reaction is highly effective in water in the prurience of KOH or HCl and was strongly affected by the steric environ-ment surrounding the carbonyl group. Aliphaflc aldehydes, ke-tones and aromatic ketones appear inert under the same reac-tion conditions.     

钒取代的杂多酸催化一锅四组分Dakin-West反应合成β-乙酰氨基酮(英文)

The multicomponent condensation of an aryl aldehyde,acetyl chloride,acetonitrile,and enolizable ketone as one-pot synthesis of β-acetamido ketones in high yields was investigated using commercial,non-corrosive,and environmentally benign Keggin and Wells-Dawson heteropolyacid catalysts.The best catalyst was H5PW10V2O40.The methodology used simple experimental conditions,and the short reaction times and high yields indicate it is a useful strategy for the large scale synthesis of β-acetamido ketones.     

Solid state reactions of nitrogenous heterocyclic compounds (Ⅱ)——Solid state reactions of indole with carbonyl compounds

Solid state Michael addition reaction of indole with α,β-unsaturaled carbonyl compounds was carried out,by which a series of compounds containing three different heterocyclic groups binding to one carbon atom were obtained.In the presence of Lewis acid,indole could undergo the solid state condensation reaction with aromatic ketones and aldehydes or quinones.The solid state reaction showed higher selectivity and yield than solution reaction The structures of products were identified by IR,1H NMR,MS,elemental analysis and X-ray crystal analysis.The reaction mechanism was also proposed.     

Application of organic selenides and tellurides in organic synthesis

This paper describes the progress on the synthesis of organic selenides and tellurides and their application in organic synthesis.Low valent selenium and telluronium compounds having high reducing selectivity can be used to form carbon-hydrogen bonds as special reducing reagents.Telluronium ylides can react with aldehydes and ketones by Wittig-type condensation to produce (E)-configuration alkenes stereoselectively.α-Phenylselanyl arsonium ylides were prepared by transyl-idation reaction of arsonium ylides with phenylselanyl halides which can undergo Wittig-type reactions with carbonyl compounds to give (Z)-α-selanyl-α,β-unsaturated compounds with high stereoselectiv-ity.Zirconium,tin,boron,halogen,metal or hetero-atom were introduced in organoselenium and telluronium compounds as new difunctional group reagents.Under transition metal catalysis,the corresponding cross coupling reactions provide new methods of formation of carbon-carbon double bonds,which were used in the stereoselective synthesis of     

Reaction of Perfluoroalkanesulfinyl Chlorides with Enamines: A Facile Synthesis of α-Perfluoroalkanesulfinyl Ketones and Aldehydes

The reaction of perfluoroalkanesulfinyl chlorides with enamines was achieved in the presence of triethylamine, and α-perfluoroalkanesulfinyl carbonyl compounds were obtained in moderate to good yields after hydrolysis of the reaction intermediates with dilute hydrochloric acid.     

Iron(III) Trifluoroacetate: Chemoselective and Recyclable Lewis Acid Catalyst for Diacetylation of Aldehydes,Thioacetalization and Transthioacetalization of Carbonyl Compounds and Aerobic Coupling of Thiols

Iron(III) trifluoroacetate [Fe(CF3CO2)3] was found to be a recyclable, highly efficient and chemoselective Lewis acid catalyst for protection of a variety of carbonyl compounds as thioacetals under nearly neutral conditions. With the use of this catalyst, 1,3-dithiolanes and 1,3-dithianes were obtained in high yields from various aldehydes. Under the same conditions ketones were similarly but more slowly thioketalized. This difference in reactivity between aldehydes and ketones was successfully utilized for the selective thioacetalization of aldehydes in the presence of ketones and also for the chemoselective conversion of β-diketone into the corresponding dithioacetal. Transthioacetalization of O,O-acetals and O,O-ketals into cyclic thioacetals was also achieved by using this catalyst. Additionally, iron(III) trifluoroacetate has been found to be efficient catalyst for the addition of acetic anhydride to both aromatic and aliphatic aldehydes to afford 1,1-diacetates (gem diacetates). Aerobic dimerization of thiols was achieved by this reagent mediated by sodium iodide and air atmosphere.     

Efficient One‐Pot Synthesis of β‐Acetamido Carbonyl Compounds Using Fe3O4 Nanoparticles

A new, one‐pot condensation of aldehydes, enolizable ketones and esters, AcCl, and MeCN, in the presence of Fe₃O₄ nanoparticles (nano‐Fe₃O₄) as an efficient catalyst, for the preparation of β‐acetamido carbonyl compounds at room temperature is described.     

Efficient Synthesis of β‐Acetamido Ketones and Esters Using Aluminum Chloride as an Inexpensive and Green Catalyst

Aluminum chloride (AlCl₃) efficiently catalyzes one‐pot multicomponent condensation of enolizable ketones or alkyl acetoacetates with aldehydes, acetonitrile and acetyl chloride to afford β‐acetamido ketone or ester derivatives in high to excellent yields and in relatively short reaction times. Moreover, by this synthetic method, some novel β‐acetamido ketones and esters (i.e. one complex structure) are prepared.     

Fe3O4@ZrO2/SO42‐: A recyclable magnetic heterogeneous nanocatalyst for synthesis of β‐amino carbonyl derivatives and synthesis of benzylamino coumarin derivatives through Mannich reaction

In the present work, we developed an effective protocol for the synthesis of β‐amino carbonyl compounds and synthesis of benzylamino coumarin derivatives through Mannich type reaction in high yields. Fe₃O₄@ZrO₂/SO₄^2‐ was employed as an effective heterogeneous nanocatalyst for the Mannich reaction. This research consists of two sections. In first section, β‐amino carbonyl derivatives were synthesized under solvent‐free condition. In the other section, benzylamino coumarin compounds were synthesized at room temperature. The present approach offers several advantages such as short reaction times, low cost, easy work‐up, mild reaction conditions, high yields and ease of recovery and reusability of the catalyst without significant loss of activity.     

Novel and Efficient One Pot Condensation Reactions between Ketones and Aromatic Alcohols in the Presence of CrO3 Producing α,β‐Unsaturated Carbonyl Compounds

We report a new, effective and simple method for preparing α,β‐unsaturated carbonyl compounds by reacting ketones and aromatic alcohols at 56°C in the presence of CrO₃ (CrO₃ acts as an oxidant and also a catalyst) for around 10 h. The condensation reactions occurred effectively among a wide combination of ketones and alcohols. The procedure is simple and the yields can be high up to 98%. And a probable mechanism is proposed.     

5-雄烯-3β, 7α, 17β-三醇和5-雄烯-3β, 7β, 17β-三醇的合成

以5-雄烯二醇为原料,用微生物转化的方法合成了两个重要的神经甾体5-雄烯-3β, 7α, 17β-三醇和5-雄烯-3β, 7β, 17β-三醇。所用菌种总枝毛霉为我们自己筛选,并首次应用于5-雄烯-3β, 7α, 17β-三醇和5-雄烯-3β, 7β, 17β-三醇的合成中。     

SmI2－Mediated Addition Reaction of α－Halomethylsulfones to Carbonyl Compounds. A Convenient Synthesis of β－Hydroxysulfones

Due to the chemoselective dehalogenation by SmI2, the addition of a-halomethylsulfones to carbonyl compounds afforded ,β-hydroxysulfones. Those reactions with α-bromomethylsulfones gave the products in moderate to good yields. The SmI2-mediated addition of gem-dihalomethylsulfones to ketones also afforded α-halo-β-hydroxysulfones in moderate yields.     

An Efficient Synthesis of 1,3‐Diphenyl‐3‐phenylamino‐propan‐1‐one and its Derivatives by Mannich Reaction in the Presence of Doped Porous Carbon by Nitrogen and Sulfur (NS‐PCS) as Catalyst

Synthesis of β‐amino carbonyl compounds by Mannich reaction involves the creation of various bonds in a single action and is attracting great attention as one of the most powerful synthetic tools for the expansion of molecular convolution and versatility. Carbon spheres (CSs) combine the advantages of carbon materials with spherical colloids, which gives them several inimitable features as catalysts. In this work, the reaction between acetophenone, aromatic aldehydes, and aromatic amines has been efficiently catalyzed by porous carbon spheres which were doped by nitrogen and sulfur (NS‐PCS) at ambient temperature to give diverse β‐amino carbonyl compounds in nearly high yields.     

过无溶剂、无催化的aza-Michael加成反应合成b氨基酸衍生物

本文报道一种安全,环境有好,经济实用的合成b氨基酸衍生物的新方法。利用α,β不饱和化合物和脂肪族胺,通过无溶剂、无催化的aza-Michael加成反应,高产率的合成b氨基酸衍生物。     

An efficient and green method for the synthesis of N‐phosphoramino o‐hydroxylphenyl α‐aminophosphonic monoesters

An efficient and green method to the synthesis of N‐protected o‐hydroxylphenyl α‐amino‐alkylphosphonic monoesters is described. It consists of the three‐component Mannich‐type reaction of phosphoramides, carbonyl compounds (aldehydes or ketones), and 2‐chlorobenzo[1,3,2] diox‐aphospholes under solvent‐free and catalyst‐free conditions, followed by hydrolysis. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:596–601, 2008; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20483     

Fragmentation Mechanism of Trans—α—Aryl—β—enamino Esters

Electron impact-induced fragmentation mechanism of Trans-α-Aryl-β-enamino esters were investigated using mass-analyzed ion kinetic energy (MIKE) spectrometry and high resolution accurate mass data It was found that the main characteristic fragmentations of compounds studied were:an odd electron ion M^ -EtOH was formed by losing a neutral molecule of ethanol;and the skeletal rearrangements took place;and the ring opening reaction happened after losing a carbon monoxide;and the typical McLafferty rearrangement underwent in ester group.The cycliztion reation caused by losing neutral molecule of TsNH2 due to the ortho-effects of substituted group of gromatic ring was also observed.