- Designing a novel tetradentate polyoxometalate eco-catalyst for the synthesis of β-aminocyclohexanone derivatives in water
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The synthesis of a series of known β-aminocyclohexanones has been accomplished using pentaerythrityl tetramethyl imidazolium phosphotungstate (C(MIM-PTA)4) as a new tetradentate acidic catalyst. It was prepared via condensation of pentaerythrityl tetrabromide with methyl imidazole. Then, bulky anion H2PW12O401? was substituted with Br? in the structure. This tetradentate catalyst provides designable cations and anions. Anions have two types of acids, acidic protons, and metals with Lewis acidity. In order to test the efficient catalytic behavior of the tetradentate catalyst, a controlled reaction was performed using benzaldehyde, aniline and cyclohexanone. Imine from the condensation of benzaldehyde and aniline was observed in the absence of ionic catalyst instead of desired products. Thus, this reaction would be attractive because of the time, energy, and raw material saving considerations because of the absence of isolation of intermediates and stereospecificity. The catalyst shows high catalytic activity such that after four recycles the product was obtained with high yield and purity. This reaction was performed at room temperature. Although high temperature could improve the reaction rate, it contributes to side reactions and oxidation of aldehyde and amine. The catalyst was characterized by elemental analysis, FT-IR spectroscopy, 1H NMR, 13C NMR, and TGA.
- Mozafari, Roya,Heidarizadeh, Fariba,Azaroon, Maedeh
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p. 40261 - 40266
(2019/01/03)
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- Tartaric acid-zinc nitrate as an efficient brnsted acid-assisted lewis acid catalyst for the mannich reaction
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Tartaric acid-zinc nitrate has been found to be an efficient Brnsted acid-assisted Lewis acid catalytic system for the facile synthesis of β-amino carbonyl compounds through the one-pot Mannich reaction of aldehydes, aromatic amines and ketones in ethanol at room temperature. Remarkable enhancement of reactivity by tartaric acid (Br?nsted acid) was observed in these reactions in the presence of anhydrous zinc nitrate (Lewis acid), due to coordination of the tartaric acid ligand to zinc ions increasing the acidity of the system. This procedure shows some advantages such as mild reaction conditions, short reaction times and high yields.
- Dong, Hao Donga,Liu, Qing,Tian, Yuanyu,Qiao, Yingyun
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p. 463 - 466
(2018/10/15)
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- H3PW12O40 anchored on graphene-grafted silica-coated MnFe2O4 as magnetic catalyst for Mannich reaction
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In this study, a three-component nanocomposite consisted of graphene, manganese ferrite and phosphotungstic acid (PTA) has been prepared. This composite, which is designated as Graphene/MnFe2O4@PTA, was synthesized through anchoring of PTA–imidazolium ionic liquid on magnetic graphene sheets. The structural and magnetic properties of the fabricated nanocomposite were studied by employing FT-IR, SEM, EDX, TEM, ICP, VSM, P-XRD and BET techniques. The synthesized magnetic nanocomposite was examined as an efficient and recyclable acidic catalyst for Mannich reaction under solvent-free conditions. The products of this reaction, which are an important class of potentially bioactive compounds, were obtained with good to excellent yields, and the catalyst could be readily recycled without any significant loss of its activity.
- Kooti,Kooshki,Nasiri,Sedeh, A. Naghdi
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p. 943 - 953
(2018/03/01)
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- H3PW12O40 supported on functionalized polyoxometalate organic-inorganic hybrid nanoparticles as efficient catalysts for three-component Mannich-type reactions in water
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Two new types of catalyst were synthesized by the immobilization of H3PW12O40 (HPW12) on the surface of organic-inorganic polyoxometalate nanoparticles of H6Cu2[PPDA]6[SiW9Cu3O37]·12H2O (HybPOM) (PPDA = p-phenylenediamine) and Go/Fe3O4/HybPOM nanoparticles. These catalysts were characterized by thermogravimetric analysis (TGA), Fourier transform infrared (FT-IR) spectroscopy, scanning electron microscopy (SEM), energy dispersive X-ray analysis (EDX) and alternating gradient force magnetometry (AGFM). The IR spectroscopy as well as XRPD reveal that HPW12 were immobilized on the support. The potentiometric titration with n-butylamine reveal that the catalysts can be classified as strong acids. The results show that the particles are mostly spherical in shape and have an average size in the range of 20-50 nm. The catalytic activities of the catalysts were probed through one-pot three-component Mannich-type reactions of aldehydes, amines and ketones in water at room temperature. The catalysts were re-used at least five times without any loss of their high catalytic activity.
- Khoshnavazi, Roushan,Bahrami, Leila,Havasi, Forugh,Naseri, Elham
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p. 11510 - 11521
(2017/02/26)
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- Bismuth Perfluoroalkylphosphinates: New Catalysts for Application in Organic Syntheses
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Commercially available BiPh3was treated with perfluoroalkylphosphinic acids [for example, (C2F5)2P(O)OH] to generate novel, highly Lewis acidic bismuth(III) perfluoroalkylphosphinates of the type PhxBi[RF2PO2]3?x(x=0, 1, 2) (RF=-C2F5, -C4F9). The first bismuth(V) perfluoroalkylphosphinate, Ph3Bi[(C2F5)2PO2]2, was synthesized from Ph3BiCl2and Ag[(C2F5)2PO2]. Examples for the successful application of the catalytically active bismuth(III) and bismuth(V) phosphinates in carbon–carbon bond forming reactions, such as Friedel–Crafts acylation and alkylation, Diels–Alder, Strecker and Mannich reaction, are presented.
- Solyntjes, Sven,Neumann, Beate,Stammler, Hans-Georg,Ignat'ev, Nikolai,Hoge, Berthold
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p. 1568 - 1575
(2017/02/10)
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- Br?nsted-Lewis dual acidic ionic liquid immobilized on mesoporous silica materials as an efficient cooperative catalyst for Mannich reactions
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Novel mesoporous silica supported ILs have been prepared and successfully applied as a heterogeneous catalyst in Mannich reactions. The excellent recyclability of the supported catalyst, mild reaction conditions, good to excellent yields, low catalyst loading, and operational simplicity are the important features of this methodology.
- Wang, Hong Bo,Yao, Nan,Wang, Long,Hu, Yu Lin
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supporting information
p. 10528 - 10531
(2017/10/03)
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- Surfactant-like Br?nsted acidic ionic liquid as an efficient catalyst for selective Mannich reaction and biodiesel production in water
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Abstract: The current study deals with the applications of a surfactant-like Br?nsted acidic ionic liquid (IL) 1-dodecyl-3-methylimidazolium hydrogen sulfate ([DMIm]HSO4) for Mannich reaction at room temperature. The reaction was efficiently preceded in water as solvent without using any harmful and expensive organic additives. Our findings showed that the reaction is selective for cyclohexanone and no Mannich product was observed when cyclopentanone was used as starting material. Density functional theory (DFT) calculations were performed to provide an evidence about the nature of reactivity of the cyclohexanone/cyclopentanone. The activity of the catalyst was also tested for biodiesel production of fatty acids with methanol and ethanol at mild thermal condition without applying additional water removal steps such as using additives or performing special methodologies like azeotropic distillation. In both reactions, the IL can be recycled and reused several times with relatively constant efficiency. Graphical Abstract: [Figure not available: see fulltext.]
- Vafaeezadeh, Majid,Karbalaie-Reza, Mina,Hashemi, Mohammad Mahmoodi,Soleimany, Kasra Qasempour
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p. 907 - 914
(2017/02/26)
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- Sulfonic acid supported on magnetic nanoparticle as an eco-friendly, durable and robust catalyst for the synthesis of β-amino carbonyl compounds through solvent free Mannich reaction
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A simple, efficient and environmentally benign solid acid catalyst was prepared by anchoring a propyl sulfonic acid on the surface of silica-coated magnetic nanoparticles by low cost precursors. The catalyst has been then engaged in the efficient β-amino carbonyl compounds production via three component Mannich reaction under solvent free reaction condition at room temperature. After the completing the reaction, the catalyst was readily separated by external magnet and reused for 10 successive rounds of reaction, without any significant loss in catalytic efficiency. The solid acidic system presented reusable strategy for the efficient synthesis of β-amino carbonyl compounds, simplicity in operation, and green aspects by avoiding toxic conventional catalysts under solvent-free condition.
- Kabiri Esfahani, Farhad,Zareyee, Daryoush,Shokuhi Rad, Ali,Taher-Bahrami, Sima
-
-
- Different ligand titanocenes complex crystal and its preparation of β - amino carbonyl compound in the application
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The invention discloses an isoligand cyclopentadiene-titanium coordination compound crystal and application thereof in preparing beta-amino carbonyl compounds. The structural formula of the cyclopentadiene-titanium coordination compound crystal is disclosed in the specification, and the cyclopentadiene-titanium coordination compound crystal is prepared from salicylic acid chelate and 3-thiophenic acid. The isoligand cyclopentadiene-titanium coordination compound crystal has the advantages of low price, no toxicity and high stability for air and water. The synthesis method has the advantages of cheap and accessible raw materials, simple and feasible synthesis steps, easy product after-treatment and high yield, and can implement gram-level preparation of the coordination compound. When being used as a cocatalyst for catalyzing the three-component Mannich reaction of cyclohexanone to prepare the beta-amino carbonyl compounds, the isoligand cyclopentadiene-titanium coordination compound crystal has the characteristics of high catalytic activity, high reaction selectivity, high product yield, no need of any solvent, simple operation process and high atom economy.
- -
-
Paragraph 0022-0029
(2017/12/28)
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- An environmentally friendly, photocontrollable and highly recyclable catalyst for use in a one-pot three-component Mannich reaction
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An environmentally friendly, photocontrollable and highly recyclable catalyst (ZrOPPAZOSO3H) has been synthesized by the immobilization of 4-[4-(6-phosphonic acid-hexanoxyl)phenylazo]benzenesulfonic acid onto zirconium phosphonate. This catalyst was characterized by Fourier transform infrared, scanning electron microscopy, X-ray powder diffraction, nitrogen adsorption-desorption and UV-vis analyses. The catalytic activity of ZrOPPAZOSO3H was investigated towards the one-pot three-component Mannich-type reaction of benzaldehyde, aniline and cyclohexanone in water at room temperature, and gave excellent yields. Interestingly, the catalytic activity could be regulated by photoirradiation. Furthermore, upon completion of the reaction, the product could be readily separated by extraction, and the water phase reused in the next run. Lastly, the catalyst could be readily recovered by centrifugation and reused up to six times without any discernible impact on its activity.
- Tang, Qian,Quan, Hong-Jiang,Liu, Song,Liu, Lan-Tao,Chow, Cheuk-Fai,Gong, Cheng-Bin
-
-
- Mesoporous silica nanoparticles (MSNs) as an efficient and reusable nanocatalyst for synthesis of β-amino ketones through one-pot three-component Mannich reactions
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Mesoporous silica nanoparticles (MSNs) proved efficient and reusable in the catalytic synthesis of β-amino ketones, through three-component Mannich reaction of ketones, aromatic aldehydes and aromatic amines under solvent-free conditions. Simple reaction conditions coupled with simple work-ups, makes this methodology a superior option for the synthesis of such β-amino ketones.
- Nasresfahani, Zahra,Kassaee, Mohammad Zaman,Nejati-Shendi, Mohammad,Eidi, Esmaiel,Taheri, Qazale
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p. 32183 - 32188
(2016/04/26)
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- Polyelectrolyte Br?nsted acid catalyzed three-component Mannich reactions accelerated by emulsion
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An effective polyelectrolyte Br?nsted acid (polyacrylic acid) catalyzed three-component Mannich reaction accelerated by emulsion has been developed. The results demonstrated that the polyacrylic acid (PAA) provided the best catalytic activity in water because of the formation of emulsions during the reaction. This newly developed simple catalyst could be recycled at least five times without any loss of activity.
- Chen, Xi,Sun, Huaming,Luo, Yanlong,Jian, Yajun,Wu, Ya,Zhang, Weiqiang,Gao, Ziwei
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p. 39343 - 39347
(2016/05/24)
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- Polyacrylic acid heterogeneous catalytic preparation of β-amino carbonyl compounds method
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The invention discloses a method for preparing a beta-amino carbonyl compound through polyacrylic acid heterogeneous catalysis. Under the polyacrylic acid catalysis condition, aldehyde, arylamine, cyclohexanone or acetone reacts directly to obtain the beta-amino carbonyl compound. Solvents are not needed to be added, used catalysts are cheap, non-toxic, stable to air, simple to operate, mild in reaction condition, short in reaction time and high in atom economy, a product is only needed to be dissolved and separated from a reactor with ethyl acetate after the reaction is finished, the catalysts can be repeatedly used, and experimental results show that the catalytic activity of the catalysts is still high after the catalysts are repeatedly used for five times, the yield of the product is basically unchanged, and the method has a wide application prospect in synthesis of the beta-amino carbonyl compound.
- -
-
Paragraph 0010-0021
(2020/05/05)
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- Graphene oxide catalytic preparation of β-amino carbonyl compounds method
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The invention discloses a method for preparing a beta-amido carbonyl compound through the catalysis of graphene oxide. The method comprises the following step of: directly compounding aromatic aldehyde, aromatic amine and aliphatic ketone under the catalytic action of the graphene oxide by taking water as a solvent to obtain the beta-amido carbonyl compound. According to the method, the used solvent is green and environment-friendly, and a used catalyst is low-cost, nontoxic and stable in the water and air. The preparation method disclosed by the invention is simple, convenient, moderate in reaction condition, short in reaction time and high in beta-amido carbonyl compound yield, and the catalyst, namely the graphene oxide, can be recycled after reaction is finished.
- -
-
Paragraph 0011-0014
(2019/02/04)
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- A magnetic solid sulfonic acid modified with hydrophobic regulators: An efficient recyclable heterogeneous catalyst for one-pot aza-Michael-type and Mannich-type reactions of aldehydes, ketones, and amines
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Two convenient green protocols for the synthesis of β-amino ketones have been developed which involve one-pot aza-Michael-type and Mannich-type reactions of a series of aldehydes, ketones, and amines in the presence of a catalytic amount of the magnetic solid sulfonic acid catalyst, Fe3O4@SiO2@Me&Et-PhSO3H, at room temperature. The catalyst can be reused four times without loss of activity.
- Movassagh, Barahman,Tahershamsi, Leili,Mobaraki, Akbar
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p. 1851 - 1854
(2015/03/30)
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- Diaryliodonium salts as efficient Lewis acid catalysts for direct three component Mannich reactions
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Diaryliodonium(iii) salts, as highly active and versatile Lewis acid catalysts for the direct three component Mannich reaction under solvent free conditions, have been investigated. The Mannich products were isolated in good to excellent yields in a very clean manner. Additionally, the catalyst could be recycled without significant loss of its catalytic activity. This journal is
- Zhang, Yanxia,Han, Jianwei,Liu, Zhen-Jiang
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p. 25485 - 25488
(2015/03/30)
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- H5CoW12O40@nanosilica: A green, bifunctional, heterogeneous nanocatalyst for one-pot three-component Mannich reaction in water
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Abstract 12-Tungestocobaltic acid, H5CoW12O40, was immobilized on nanosilica from rice husk ash to produce H5CoW12O40@nanosilica as a bifunctional nanocatalyst. The TEM result showed that the particles are mostly spherical in shape, and that they have an average size of approximately 10 nm. The catalytic activity of this catalyst was investigated in Mannich reaction of various aldehydes, ketones, and amines in water. This rapid procedure afforded structurally diverse β-amino ketones in high to excellent yields. Short reaction time, simple work-up procedure, elimination of toxic solvents, and low catalyst loading are the advantages of this procedure.
- Rafiee, Ezzat,Kahrizi, Masoud
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p. 2833 - 2839
(2015/04/27)
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- One-pot three-component Mannich reaction in water catalyzed by eco-friendly, hydrophobic and recyclable sulfonic acid based nanosilica (SBA-15-Ph-PrSO3H)
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A mild, effective and green method for the Mannich reaction of aromatic aldehydes, aromatic amines and ketones has been accomplished in good to excellent yields using hydrophobic SBA-15-Ph-PrSO3H in water at room temperature. This new method consistently has the advantages of excellent yields, short reaction times, and non-toxic nature and reusability of the catalyst. Additionally, utilization of water as a green solvent, simple reaction conditions, isolation, and purification make this manipulation interesting from an environmental perspective. the Partner Organisations 2014.
- Zareyee, Daryoush,Alizadeh, Hamidreza
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p. 37941 - 37946
(2014/11/07)
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- One-pot three-component Mannich reaction in water catalyzed by eco-friendly, hydrophobic and recyclable sulfonic acid based nanosilica (SBA-15-Ph-PrSO3H)
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A mild, effective and green method for the Mannich reaction of aromatic aldehydes, aromatic amines and ketones has been accomplished in good to excellent yields using hydrophobic SBA-15-Ph-PrSO3H in water at room temperature. This new method consistently has the advantages of excellent yields, short reaction times, and non-toxic nature and reusability of the catalyst. Additionally, utilization of water as a green solvent, simple reaction conditions, isolation, and purification make this manipulation interesting from an environmental perspective. This journal is
- Zareyee, Daryoush,Alizadeh, Hamidreza
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p. 37941 - 37946
(2015/02/19)
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- Bronsted acid-surfactant-combined catalyst for the Mannich reaction in water
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A series of Bronsted acid-surfactant-combined catalysts (BASCs) functionalised with different acids have been synthesized and applied to catalyze the three-component Mannich reaction with aldehyde, acetone and amine at 25 °C in water. The effects of cation tail length and ions of the ionic liquid and the recyclability of the catalysts and BASC acidity (H0) were investigated. The results demonstrated that the 3-(N,N- dimethyloctylammonium) propanesulfonic acid toluene sulfate ([DOPA][Tos]) provide the best catalytic activity because of the formation of emulsions during the reaction. The catalytic procedure was simple and the catalyst could be recycled 9 times by simple separating processes without noticeably decreasing the catalytic activity. The Royal Society of Chemistry 2014.
- Chang, Tao,He, Leqin,Bian, Li,Han, Haiyan,Yuan, Mingxia,Gao, Xiaorui
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p. 727 - 731
(2014/01/06)
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- Modification of poly(vinyl chloride) with pendant metal complex for catalytic applications
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Poly(vinyl chloride) was modified to develop an alternative support for the preparation of polymer-supported catalysts. Commercially available poly(vinyl chloride) was synthetically modified to a polymer containing pendant primary amino groups. The Schiff-base of salicylaldehyde and the amino polymer were prepared and were used as the ligands in the synthesis of a polymer-supported copper complex. The polymer-supported ligand and catalysts were characterized by various physical methods. The polymer with the pendant copper complex was able to catalyze the one-pot three-component Mannich reaction between aldehydes, ketones and anilines under mild and environmentally friendly conditions. The catalyst can be recovered by simple filtration and is reusable.
- Krishnan, Gopalakrishnapanicker Rajesh,Sreeraj, Modiyuzhathil K.,Sreekumar, Krishnapillai
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p. 736 - 741
(2013/08/23)
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- SnTUD-1: A solid acid catalyst for three component coupling reactions at room temperature
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A novel wormhole structured mesoporous material containing tin, SnTUD-1, was prepared by a direct hydrothermal synthesis method using triethanolamine (TEA) as an organic inexpensive mesoporous structure directing agent. XRD and N2 sorption studies of SnTUD-1 confirmed the amorphous mesoporous nature of SnTUD-1, which possessed a large surface area of 555 m2 g-1 and a pore diameter of 7.4 nm. HR-TEM further ascertained the disordered pores in their morphology and the presence of nano-domains of SnO2 species. The nature of the Sn4+ ion co-ordination with the silica matrix was evaluated by using different techniques including diffuse reflectance UV-Vis, FTIR, 29Si MAS NMR and XPS. SnTUD-1 had an interesting Lewis acidity as measured by FTIR of pyridine adsorption which provided excellent activities in one-pot three-component Mannich-type reactions of ketones with aldehydes and amines at room temperature.
- Pachamuthu, Muthusamy Poomalai,Shanthi, Kannan,Luque, Rafael,Ramanathan, Anand
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supporting information
p. 2158 - 2166
(2013/09/24)
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- Diastereoselective three-component Mannich reaction catalyzed by silica-supported ferric hydrogensulfate
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A highly anti-diastereoselective three-component Mannich reaction of aromatic amines and aromatic aldehydes with cyclohexanone in the presence of silica-supported ferric hydrogensulfate has been developed. The best selectivity was obtained where there were electron-donating groups on both aldehyde and amine. Selectivity decreases when electron-withdrawing groups are present on the aldehyde; in these cases selectivity is improved if an electron-donating group is present on the amine.
- Eshghi, Hossein,Rahimizadeh, Mohammad,Hosseini, Mohsen,Javadian-Saraf, Aida
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p. 197 - 203
(2013/07/27)
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- Nafion-H: A recyclable and diastereoselective solid acid catalyst for three-component mannich reaction
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One-pot, three-component Mannich reactions of ketones, aldehydes and amines are efficiently catalyzed by heterogeneous Nafion-H at ambient temperature to give the corresponding β-amino ketones compounds in good to excellent yields. The catalyst can be easily recovered and reused without any decrease of activity for at least four times. Diastereoselective products can be obtained in Mannich reaction of aliphatic ketone. Pleiades Publishing, Ltd., 2012.
- Suling, Yang,Gang, Li,Yunling, Long
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p. 689 - 693
(2013/02/23)
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- An efficient synthesis of β-aminoketone compounds through three-component Mannich reaction catalyzed by calcium chloride
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Various β-aminoketones were synthesized in a three-component reaction of ketones, aldehydes, and amines in the presence of calcium chloride as catalyst in ethanol in high yields as compared to other synthetic methods. The advantages of this new method are a short reaction time (2 h), high yields, easy workup, convenience, low cost, and eco-friendly protocol. Springer-Verlag 2011.
- Kulkarni, Pramod,Totawar, Balaji,Zubaidha, Pudukulathan K.
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experimental part
p. 625 - 629
(2012/07/14)
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- One-pot three-component Mannich reaction catalyzed by iodine under solvent-free conditions
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One-pot three-component Mannich reactions of ketones with aromatic aldehydes and aromatic amines are effectively catalyzed by molecular iodine at room temperature under solvent-free conditions to afford the corresponding β-amino carbonyl compounds with moderate to excellent yields. The method has the following advantages: no use of solvent, mild condition, high reaction speed and small quantity of catalyst.
- Gang, Li,Ruiling, Long,Jiangli, Yang
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experimental part
p. 397 - 400
(2011/08/03)
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- H3PW12O40 supported on silica-encapsulated γ-Fe2O3 nanoparticles: A novel magnetically- recoverable catalyst for three-component Mannich-type reactions in water
-
A new type of magnetically-recoverable catalyst was synthesized by the immobilization of H3PW12O40 on the surface of silica-encapsulated γ-Fe2O3 nanoparticles. This catalyst was characterized by transmission electron microscopy (TEM), a laser particle size analyzer, infrared spectroscopy (IR) and inductively coupled plasma atomic emission spectroscopy (ICP-AES). The results show that the particles are mostly spherical in shape and have an average size of approximately 94 nm. The characterization data derived from IR spectroscopy reveal that H3PW12O40 on the support exists in the Keggin structure. The acidity of the catalyst was measured by a potentiometric titration with n-butylamine. To our surprise, this very strong solid acid catalyst showed an excellent distribution of acid sites, suggesting that the catalyst possesses a higher number of surface active sites compared to its homogeneous analogues. The activity of the catalyst was probed through one-pot three-component Mannich-type reactions of aldehydes, amines and ketones in water at room temperature. The excellent conversions show that the catalyst has strong and sufficient acidic sites, which are responsible for its catalytic performance. After the reaction, the catalyst/product separation could be easily achieved with an external magnetic field, and more than 95% of the catalyst could usually be recovered. The catalyst was reused at least five times without any loss of its high catalytic activity.
- Rafiee, Ezzat,Eavani, Sara
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experimental part
p. 2116 - 2122
(2011/10/09)
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- 2-pyrrolidinecarboxylic acid ionic liquid as a highly efficient organocatalyst for the asymmetric one-pot Mannich reaction
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A. novel one-pot: three-component asymmetric Mannich reaction using [EMIm][PrO] (1) as a catalyst has been developed. By employing this new reaction system, a variety of optically active ss-amino carbonyl compounds were synthesized in up to 99% yield with up to >99 dr and >99% ee. The reaction conditions have been optimized and the mechanism for the asymmetric induction is discussed.
- Zheng, Xin,Qian, Yun-Bo,Wang, Yongmei
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experimental part
p. 515 - 522
(2010/04/24)
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- Cerium chloride (CeCl3·7H2O) as a highly efficient catalyst for one-pot three-component Mannich reaction
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We have demonstrated the use of CeCl3·7H2O as highly efficient catalyst for one-pot threecomponent Mannich reaction to afford β-amino carbonyl compounds in good to excellent yield within shorter period of reaction time. The process is mild, efficient, environmentally benign with the use of little amount of catalyst.
- Kidwai, Mazaahir,Jahan, Anwar
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experimental part
p. 2175 - 2179
(2011/10/09)
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- Utilization of biocatalytic promiscuity for direct Mannich reaction
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A lipase-catalyzed direct Mannich reaction of arylamines with aromatic aldehydes and ketones including cyclohexanone, butanone and 1-hydroxy-2- propanone was developed under EtOH/H2O system in a "one-pot" strategy. A series of experiments on the promiscuous activity of lipases were performed to optimize the biocatalytic process, and a wide scope of substrates was expanded with good yields.
- He, Ting,Li, Kun,Wu, Ming-Yu,Feng, Xing-Wen,Wang, Na,Wang, Hai-Yang,Li, Chao,Yu, Xiao-Qi
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experimental part
p. 189 - 194
(2011/01/13)
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- Cs2.5H0.5PW12O40 catalyzed diastereoselective synthesis of β-amino ketones via three component Mannich-type reaction in water
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A series of insoluble salts of Keggin heteropoly compounds were prepared and used as catalysts for the Mannich-type reaction of benzaldehyde, aniline, and cyclohexanone in water. Among them, Cs2.5H0.5PW 12O40 showed excellent catalytic activity. Effects of surfactant, catalyst loading and temperature were studied to introduce the best reaction condition. The optimized reaction conditions were extended to Mannich reaction of various aldehydes, ketones, and amines in water. This rapid procedure afforded structurally divers β-amino ketones with major anti diastereoselectivity. Additionally, four new compounds were reported. The catalyst was recovered and reused for subsequent runs.
- Rafiee, Ezzat,Eavani, Sara,Nejad, Fereshte Khajooei,Joshaghani, Mohammad
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experimental part
p. 6858 - 6863
(2010/09/18)
-
- Synthesis and structure of an air-stable hypervalent organobismuth (III) perfluorooctanesulfonate and its use as high-efficiency catalyst for Mannich-type reactions in water
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An air-stable hypervalent organobismuth (III) perfluorooctanesulfonate was synthesized and characterized by spectroscopic and X-ray crystallographic techniques, and found to exhibit high catalytic efficiency towards one-pot Mannich-type reaction of ketones with aromatic aldehydes and aromatic amines in water. This catalyst also shows good recyclability and reusability. This catalytic system would provide a simple, efficient and 'green' avenue towards the synthesis of β-amino ketones.
- Zhang, Xiaowen,Yin, Shuangfeng,Qiu, Renhua,Xia, Jun,Dai, Weili,Yu, Zhenying,Au, Chak-Tong,Wong, Wai-Yeung
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experimental part
p. 3559 - 3564
(2010/01/18)
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- Three component mannich reaction and 1,5-benzodiazepine synthesis catalyzed by a tetranitrile-silver complex
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This manuscript describes the first example of silver ion complex of a dendritic tetranitrile ligand catalyzed one-pot three component Mannich reaction and 1,5-benzodiazepine synthesis. The catalyst can be separated from the products by a change in the solvent. The catalyst is reusable.
- Krishnan, Gopalakrishnapanicker Rajesh,Sreerekha, Radhakrishnan,Sreekumar, Krishnapillai
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experimental part
p. 17 - 21
(2010/04/23)
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- Novel one-pot Cu-nanoparticles-catalyzed Mannich reaction
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Recyclable heterogeneous Cu-nanoparticles efficiently catalyzed the one-pot three-component Mannich reaction of ketones, aromatic aldehydes and amines in methanol. This method provides a novel and improved method for obtaining β-amino carbonyl compounds in terms of good yield with little catalyst loading.
- Kidwai, Mazaahir,Mishra, Neeraj Kumar,Bansal, Vikas,Kumar, Ajeet,Mozumdar, Subho
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body text
p. 1355 - 1358
(2009/06/28)
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- One-pot, three-component Mannich-type reaction catalyzed by functionalized ionic liquid
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A three-component Mannich-type reaction of aromatic aldehydes, aromatic amines, and ketones was catalyzed by a novel functionalized ionic liquid, 3-(N,N-dimethyldodecylammonium)propanesulfonic acid hydrogen sulfate ([DDPA][HSO4]) at room temperature to give various β-amino carbonyl compounds in good yields. The catalyst could be reused at least six times without noticeably reducing catalytic activity.
- Fang, Dong,Gong, Kai,Zhang, Dai-Zhen,Liu, Zu-Liang
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experimental part
p. 1325 - 1329
(2010/05/19)
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- Carbohydrate-based tolylsulfonyl hydrazines: Effective catalysts for the Mannich reaction and the syntheses of bisindolylalkanes in water
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Three carbohydrate-based tolylsulfonyl hydrazines were used to catalyze the three-component Mannich reaction, as well as the adduct reaction of aldehyde and indole to prepare bisindolylalkanes in water. Moderate to good yields were achieved. The results demonstrate that carbohydrate derivatives can be employed as effective catalysts in water, and an environmentally benign methodology was developed to synthesize bioactive bisindolylalkanes and the β-amino carbonyl framework. CSIRO 2008.
- Wu, Peng,Wan, Yiqian,Cai, Jiwen
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p. 359 - 363
(2008/09/19)
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- Quaternary ammonium salt gemini surfactants containing perfluoroalkyl tails catalyzed one-pot Mannich reactions in aqueous media
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A newly prepared quaternary ammonium salt (QAS) gemini fluorosurfactants efficiently catalyze one-pot Mannich reactions of aldehydes, amines and ketones in aqueous media at ambient temperature to afford corresponding β-aminocarbonyl compounds in good to excellent yields. In addition, the gemini fluorosurfactant catalysts were recovered and reused for three times with little loss of their catalytic activities.
- Shen, Wei,Wang, Li-Min,Tian, He
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p. 267 - 273
(2008/12/20)
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- An efficient and mild bismuth triflate-catalysed three-component Mannich-type reaction
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In the presence of a catalytic amount of Bi(OTf)3·4H 2O, aldehydes together with amines react with silyl enolates to afford the corresponding Mannich-type adducts smoothly. A wide variety of silyl enolates derived from ketones, as well as esters and thioesters, react rapidly to afford the β-amino ketones or the β-amino esters in high yields (up to 94%). The Royal Society of Chemistry.
- Ollevier, Thierry,Nadeau, Etienne
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p. 3126 - 3134
(2008/04/01)
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- Stereoselective synthesis of β-amino ketones via direct Mannich-type reaction catalyzed with silica sulfuric acid
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At room temperature, the direct Mannich-type reaction of a variety of in situ generated aldimines using aldehydes and anilines with ketones in a three-component reaction was efficiently catalyzed by silica sulfuric acid (SSA) in EtOH. This rapid reaction afforded the corresponding β-amino ketones in good yields with excellent stereoselectivities and catalyst was recyclable.
- Wu, Hui,Shen, Yang,Fan, Li-yan,Wan, Yu,Zhang, Pu,Chen, Cai-fa,Wang, Wen-xiang
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p. 2404 - 2408
(2007/10/03)
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- Basic functionalized ionic liquid catalyzed One-pot mannich-type reaction: Three component synthesis of β-Amino carbonyl compounds
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Three-component Mannich-type reaction of cyclohexanone, aromatic aldehydes, and aromatic amines was catalyzed by a basic functionalized ionic liquid, 1-butyl-3-methylimidazolium hydroxide ([bmim][OH]), at room temperature to give various β-amino carbonyl compounds in high yields. The ionic liquid, which is environmentally friendly, can be recycled at least 5 times without significant loss of activity.
- Gong, Kai,Fang, Dong,Wang, Hua-Lan,Liu, Zu-Liang
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p. 1195 - 1198
(2008/03/27)
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- Mannich-type reactions in a colloidal solution formed by sodium tetrakis(3,5-trifluoromethylphenyl)borate as a catalyst in water
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Sodium tetrakis(3,5-trifluoromethylphenyl)borate [NaBAr4F] efficiently catalyzed the one-pot, three-component Mannich reaction of ketones with aromatic aldehydes and different anilines in water at an ambient temperature and afforded the corresponding β-amino carbonyl compounds in good to excellent yields.
- Chang, Chi-Tsing,Liao, Bei-Sih,Liu, Shiuh-Tzung
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p. 9257 - 9259
(2008/02/10)
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- A heterogeneous silica-supported scandium/ionic liquid catalyst system for organic reactions in water
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(Figure Presented) Several carbon-carbon bond-forming reactions are catalyzed by a silica-supported scandium triflate catalyst combined with an ionic liquid. The combination of these two components creates a hydrophobic reaction environment in water (see scheme; blue: water, yellow: substrate, orange: ionic liquid).
- Gu, Yanlong,Ogawa, Chikako,Kobayashi, Juta,Mori, Yuichiro,Kobayashi, Shu
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p. 7217 - 7220
(2007/10/03)
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- Synthesis of β-amino carbonyl compounds via a Zn(OTf)2-catalyzed cascade reaction of anilines with aromatic aldehydes and carbonyl compounds
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A Zn(OTf)2-catalyzed cascade reaction of anilines with aromatic aldehydes and carbonyl compounds was described. This one-pot three-component reaction afforded the corresponding β-amino carbonyl compounds, β-amino esters, and β-amino ketones in good to excellent yields. The reaction was also applied for the liquid-phase synthesis of β-amino carbonyl compound library using PEG as a support.
- Yang, Yun-Yun,Shou, Wang-Ge,Wang, Yan-Guang
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p. 10079 - 10086
(2007/10/03)
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- Mannich-type reactions of aromatic aldehydes, anilines, and methyl ketones in fluorous biphase systems created by rare earth (III) perfluorooctane sulfonates catalysts in fluorous media
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Rare earth (III) perfluorooctane sulfonates (RE(OPf)3) catalyze the three-component Mannich-type reactions of different ketones with various aromatic aldehydes and aromatic amines in fluorous media to give various β-arylamino ketones in good yields. By simple separation of the fluorous phase containing only catalyst, reaction can be repeated several times.
- Yi, Wen-Bin,Cai, Chun
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p. 1515 - 1521
(2008/09/16)
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- Highly efficient one-pot three-component Mannich reaction in water catalyzed by heteropoly acids
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Heteropoly acids efficiently catalyzed the one-pot, three-component Mannich reaction of ketones with aromatic aldehydes and different amines in water at ambient temperature and afforded the corresponding β-amino carbonyl compounds in good to excellent yields and with moderate diastereoselectivity. This method provides a novel and improved modification of the three-component Mannich reaction in terms of mild reaction conditions and clean reaction profiles, using very a small quantity of catalyst and a simple workup procedure.
- Azizi, Najmodin,Torkiyan, Lalleh,Saidi, Mohammad R.
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p. 2079 - 2082
(2007/10/03)
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- HCl-catalyzed stereoselective Mannich reaction in H2O-SDS system
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HCl-catalyzed Mannich reaction of cyclic ketone, aromatic aldehyde, and aromatic amine proceeded smoothly in water in the presence of SDS to afford the corresponding β-amino ketone with high anti selectivity.
- Akiyama, Takahiko,Matsuda, Keiichiro,Fuchibe, Kohei
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p. 322 - 324
(2007/10/03)
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- Molecular iodine-catalyzed imine activation for three-component nucleophilic addition reactions
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β-Amino ketones and α-amino nitriles were synthesized from silyl enol ethers and trimethylsilyl cyanides, via a three-component nucleophilic addition reaction with aromatic aldehydes and amines; the reaction was found to be significantly accelerated by molecular iodine under neutral conditions.
- Lee, Byoung Se,Mahajan, Suresh,Janda, Kim D.
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p. 1325 - 1327
(2007/10/03)
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- Solvent-free imino-aldol three-component couplings on a conveniently-prepared and reusable phosphoric acid-silica gel support
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A new solvent-free procedure for the synthesis of β-amino carbonyl compounds in generally moderate to excellent yields has been developed. Three-component Mannich-type couplings between aldehydes (aromatic, aliphatic, alicyclic, and heterocyclic), aromatic amines and silyl enol equivalents proceeded smoothly on a conveniently prepared and reusable phosphoric acid-silica gel solid support.
- Lock, Sandra,Miyoshi, Norikazu,Wada, Makoto
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p. 1308 - 1309
(2007/10/03)
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- Synthesis of Peroxy-Containing Acetylenic Alcohols and Ethers Derived from γ-Amino Ketones
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A series of peroxy-containing tertiary alcohols were prepared by the reactions of lithium peroxy acetylenides with γ-amino ketones. The reactions of the intermediate lithium peroxy alcoholates with alkyl iodides in the presence of hexamethylphosphoramide yielded the corresponding peroxy ethers. The thermal stability of the compounds synthesized was evaluated by thermal analysis.
- Dikusar,Kozlov,Popova,Moiseichuk,Yuvchenko
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p. 591 - 595
(2007/10/03)
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