- Tuning Microenvironment of Quaternary Ammonium Salt and Tertiary Amine Bifunctionalized Polyacrylonitrile Fiber for Cooperatively Catalyzed Aza-Michael Addition
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A series of novel polyacrylonitrile fiber catalysts modified with different ratio of quaternary ammonium salt (QA) to tertiary amine (TA) were screened for heterogeneously catalyzed aza-Michael addition in water. The best catalyst was found to be PAN
- Yuan, Xueyu,Du, Huimin,Zhao, Jingyan,Chima, Anyaegbu Ejike,Ma, Ning,Tao, Minli,Zhang, Wenqin
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p. 832 - 843
(2020/08/10)
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- Synthesis of β-Amino Ketones using graphene oxide: a benign carbonaceous acid catalyst for Mannich reaction
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Abstract: Simple and easily preparable graphene oxide (GO) is used as a straightforward carbocatalyst for the synthesis of β-amino ketones via a 3-component Mannich reaction under mild condition. The native GO is acting as a carbonaceous solid Br?nsted acid catalyst without any special functionalization, yielding a spectrum of β-amino ketones under metal-free conditions. The present catalytic method offers a benign and simple procedure without any hazardous workup, and chromatographic purification resulted in an excellent yield of β-amino ketones. The catalyst has shown good sustainability up to 6 consecutive catalytic cycles without any significant loss in its activity. The stability of the recovered catalyst is proved by analytical techniques such as FT-IR, PXRD, SEM, and TEM. This mild solid-acid catalyst offers an alternative and sustainable approach to get synthetically essential β-amino ketones under greener conditions. Graphical abstract: [Figure not available: see fulltext.].
- Saravana Ganesan, Nagappan,Suresh, Palaniswamy
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p. 1197 - 1210
(2021/01/07)
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- Graphene oxide as a catalyst for one-pot sequential aldol coupling/aza-Michael addition of amines to chalcones through in situ generation of Michael acceptors under neat conditions
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Graphene oxide (GO) in conjunction with tetra n-butyl ammonium bromide (TBAB) was found to function as an efficient catalyst for one-pot sequential aldol coupling/aza-Michael addition of amines to chalcones in a single reaction vessel. Benzaldehydes and acetophenone were coupled in situ to produce their corresponding chalcones which underwent a subsequent aza-Michael addition under solvent-free condition. This procedure avoids the use of precious metals and the heterogeneous nature of the GO simplifies purification and isolation of the products by simple filtration of the catalyst.
- Khalili, Dariush,Lavian, Salime,Moayyed, Mohammadesmaeil
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- Ionic liquid-immobilized proline(s) organocatalyst-catalyzed one-pot multi-component Mannich reaction under solvent-free condition
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A highly efficient clean and simple methodology has been established for the one-pot Mannich reaction using ionic liquid-immobilized proline(s) organocatalyst under solvent-free conditions. The three components comprising substituted acetophenones, substituted aromatic aldehydes and substituted aromatic amines underwent Mannich reactions in the presence of 7?mol% of ionic liquid-immobilized proline(s) organocatalyst to provide β-amino carbonyl compounds in 2–3?h at room temperature with excellent yields. This methodology provides several advantages such as mild reaction conditions, short reaction time, low catalyst loading percentage, multi-component approach, transition metal-free and solvent-free synthesis. The ionic liquid-immobilized proline(s) organocatalyst was recycled and reused five times without a significant loss of its catalytic activity.
- Prabhakara,Maiti, Barnali
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p. 2381 - 2401
(2020/01/31)
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- An uncommon use of irradiated flavins: Br?nsted acid catalysis
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We present that thioacetalization of aldehydes can be induced by blue light irradiation in the presence of a catalytic amount of riboflavin tetraacetate (RFTA) under aerobic conditions. Several control experiments have suggested that the reaction is more
- Arakawa, Yukihiro,Mihara, Tomohiro,Fujii, Hiroki,Minagawa, Keiji,Imada, Yasushi
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supporting information
p. 5661 - 5664
(2020/06/09)
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- Design, and facile synthesis of 1,3 diaryl-3-(arylamino)propan-1-one derivatives as the potential alpha-amylase inhibitors and antioxidants
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Diabetes is the most prevalent metabolic disorder causing a high rate of mortality and morbidity. Recently alpha-amylase is reported to be good drug design target for the treatment of diabetes mellitus. We have designed 116 molecules based on aza-Michael
- Bashary, Roqia,Khatik, Gopal L.
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p. 156 - 162
(2018/10/20)
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- Cellulose-Supported Ionic Liquid Phase Catalyst-Mediated Mannich Reaction
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Cellulose-supported ionic liquid phase (SILP) catalyst containing a camphor sulfonate anion with a pendant ferrocenyl group was prepared and characterised with different analytical techniques such as Fourier-transform infrared, Fourier-transform Raman, and cross polarization-magic angle spinning (CP-MAS) 13C NMR spectroscopy, X-ray diffraction, scanning electron microscopy, and thermogravimetric analysis. The SILP catalyst displayed excellent catalytic activity in the synthesis of β-amino carbonyl compounds by Mannich reaction. Recycling studies revealed that SILP catalyst could be reused six times without significant decrease in catalytic activity.
- Khanapure, Sharanabasappa,Jagadale, Megha,Kale, Dolly,Gajare, Shivanand,Rashinkar, Gajanan
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p. 513 - 523
(2019/05/15)
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- Titanium tetrachloride incorporated crosslinked polystyrene copolymer as an efficient and recyclable polymeric Lewis acid catalyst for the synthesis of Β-amino carbonyl compounds at room temperature
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An efficient and eco-friendly procedure for one-pot synthesis of β-amino carbonyl compounds by three-component reaction of aromatic aldehydes, acetophenone, and aromatic amines via a Mannich type reaction using a stable tightly bound complex, titanium tetrachloride incorporated crosslinked polystyrene copolymer (PS/TiCl4), as a water tolerant, recoverable, and reusable polymeric Lewis acid catalyst in ethanol at room temperature is reported. The complex of the polystyrene and TiCl4 provides a shelf-stable acidic, water tolerant material, and it is not easily hydrolyzed by water. Our findings thus show a novel and improved modification of the Mannich type reaction in terms of mild reaction conditions, clean reaction profiles, applicability to various substrates using a simple workup procedure which makes this reaction an interesting alternative to previously applied procedures. The recyclability of the catalyst makes this protocol environmentally benign.
- Rahmatpour, Ali,Eeimen, Reza,Goodarzi, Niloofar
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p. 2915 - 2930
(2019/08/30)
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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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- Ultrasound-promoted synthesis of-Amino carbonyl compounds via a mannich reaction catalyzed by ionic liquids
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Background: Mannich reaction is one of the most important carbon-carbon bond formation reactions in organic synthesis. Traditional methods require a large amount of ungreen catalysts or much longer reaction time, which limits the scope of their application. So, a recyclable catalyst with high activity and selectivity is highly appreciated, and the highly shortened reaction time is also very appealing. Methods: An efficient and facile process to prepare a series of -Amino carbonyl compounds was found via Mannich reactions catalyzed by caprolactam-based Br?nsted acidic ionic liquids under ultrasonic irradiation. Results: [Capl][BF4] was the most effective catalyst in the Mannich reaction, and good yields was gained within 2-6 h. The activity and stability of the catalyst was maintained very well even after five times, and ultrasound can effectively shorten the reaction time and enhance the yield at ambient condition. Conclusion: A convenient procedure for Mannich reaction using acidic ILs catalyst under ultrasonic irradiation has been designed with many superiorities, such as simple manipulation, less reaction time and high yields. The Mannich reaction takes place in no presence of organic solvents such as toluene or ethanol, etc. The new synthetic method reported in this paper would make appreciable contribution to the subject of environmental friendly chemistry and it is available for industrial applications.
- Qian, Hua,Kai, Wang,Zhen, Juejie
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p. 143 - 147
(2016/03/01)
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- The zeolite ZSM-5-SO3H catalyzed aza-Michael addition of amines and sulfonamides to electron-deficient alkenes under solventfree conditions
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Aza-Micheal addition of aromatic and aliphatic amines and sulfonamides to α,β-unsaturated esters, ketones and nitriles has been developed using the zeolite ZSM-5-SO3H as catalyst under solvent-free conditions.
- Douraki, Saba Mohammadi,Massah, Ahmad Reza
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p. 1346 - 1349
(2015/11/10)
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- The zeolite ZSM-5-SO3H catalyzed aza-Michael addition of amines and sulfonamides to electron-deficient alkenes under solvent-free conditions
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Aza-Micheal addition of aromatic and aliphatic amines and sulfonamides to α,β-unsaturated esters, ketones and nitriles has been developed using the zeolite ZSM-5-SO3H as catalyst under solvent-free conditions.
- Douraki, Saba Mohammadi,Massah, Ahmad Reza
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p. 1346 - 1349
(2016/02/26)
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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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- PPh3-catalyzed Mannich reaction: A facile one-pot synthesis of β-amino carbonyl compounds under solvent-free conditions at room temperature
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PPh3 was used as an efficient catalyst for the one-pot three-component Mannich reactions of acetophenone with different aromatic amines and aromatic aldehydes under solvent-free conditions at room temperature. This method provides a novel and improved method for preparing β-amino carbonyl compounds in the absence of acidic catalyst in excellent yield. Little catalyst loading, easy accessibility of the catalyst, mild conditions, and simple work-up procedure are the main features of this protocol.
- Abedini-Torghabeh, Javad,Eshghi, Hossein,Bakavoli, Mehdi,Rahimizadeh, Mohammad
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p. 3649 - 3658
(2015/06/08)
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- Design of Supported Organocatalysts from Carboxylic Acids for the Mannich-Type Synthesis of β -Amino Carbonyl Compounds
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New supported acidic organocatalysts were prepared by the impregnation of three carboxylic acids (CF3COOH, CCl3COOH, and CH3COOH) on silica support at room temperature in diethyl ether. The catalysts were characterized by scanning electron microscopy, energy dispersion X-ray analysis (EDX), Brunauer-Emmett-Teller-surface-area-analysis (BET), thermogravitational analysis, Fourier transform infrared, and powder X-ray diffractometry analysis. These solid acids were observed as highly efficient reusable catalysts at room temperature for the selective synthesis of β-amino carbonyl compounds via Mannich-type reactions of acetophenone, arylamine and arylaldehydes using two different conditions in CH2Cl2 solution and solvent-free grinding within a short time. The more acidic two catalysts could be recycled for up to five cycles with a small loss in catalytic activity.
- Sarma, Parishmita,Saikia, Susmita,Borah, Ruli
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supporting information
p. 2810 - 2822
(2015/12/23)
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- Starch solution as an efficient and environment-friendly catalyst for one-pot synthesis of β-aminoketones and 2,3-dihydroquinazolin-4(1H)-ones in EtOH
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An efficient, practical and atom-efficient method has been developed for the preparation of β-aminoketones and 2,3-dihydroquinazoline-4(1H)-ones via multicomponent one-pot reaction in starch solution as an entirely green catalyst. The advantages of this novel protocol are high yields, short reaction time, simple methodology, easy work-up and purification, lack of toxicity and eco-friendly catalyst. Graphical Abstract: [Figure not available: see fulltext.].
- Maghsoodlou, Malek Taher,Khorshidi, Naimeh,Mousavi, Mir Rasul,Hazeri, Nourallah,Habibi-Khorassani, Sayyed Mostafa
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p. 7497 - 7508
(2015/09/29)
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- MgO nanoparticles as an efficient and reusable catalyst for aza-Michael reaction
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MgO nanoparticles were prepared by an improved sol-gel technique which appeared to have narrow size distributions. The synthesized magnesium oxide nanoparticles were used as an efficient catalyst in aza-Michael reaction for addition of amines to a series of α,β-unsaturated carbonyl compounds and nitro olefins under solvent-free conditions at room temperature to afford high yields of the β-amino carbonyl and β-nitro amines. The catalyst can be recovered and reused at least five successive runs without loss of activity. Graphical abstract: [Figure not available: see fulltext.]
- Tajbakhsh, Mahmood,Farhang, Maryam,Hosseini, Ali Asghar
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p. 665 - 672
(2014/05/20)
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- PEG 1000-based dicationic acidic ionic liquid as an efficient catalyst for mannich-type reaction in water
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GRAPHICAL ABSTRACT PEG1000-based dicationic acidic ionic liquid (PEG1000-DAIL) was found to be an efficient and recyclable catalyst for Mannich-type reaction of different ketones with various aromatic aldehydes and aromatic amines in water to give various β-arylamino ketones in good yields. The catalytic system could be easily recovered and reused for at least six runs only with slight decrease in its activity.
- Ren, Yi-Ming,Shao, Juan-Juan,Wu, Zhi-Chuan,Yang, Ren-Chun,Zhang, Ze,Tao, Ting-Xian
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supporting information
p. 2529 - 2534
(2014/08/05)
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- An environmentally benign protocol: Catalyst-free Michael addition of aromatic amines to α,β-unsaturated ketones in glycerol
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Glycerol was used as a reaction medium as well as promoter for aza-Michael addition of aromatic amines to electronic deficient α,β-unsaturated ketones. Various aromatic amines can react smoothly with chalcone, 2-cyclohexen-1-one, 2-cyclopenten-1-one, and
- Ying, Anguo,Zhang, Qunhui,Li, Hongmin,Shen, Gangfeng,Gong, Weizhong,He, Mingju
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p. 517 - 525
(2013/07/27)
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- Ionic amino acids: Application as organocatalysts in the aza-Michael reaction
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The ethyl methyl imidazolium salts of amino acids, [emim][AA], have been used as catalysts in the aza-Michael reaction. Furthermore, when chiral amino acids were used, a stereoselective reaction was achieved. The mechanism of the transformation was verified by the detection of a key intermediate by electrospray ionization mass spectroscopy (ESI-MS).
- Morimoto, Naoki,Takeuchi, Yasuo,Nishina, Yuta
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-
- Decarboxylative Mannich reactions
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p-Methoxyphenylimines obtained from enolizable aldehydes react in the absence of catalysts at room temperature with β-keto carboxylic acids through a decarboxylative Mannich reaction. The Mannich products were obtained with a high degree of anti selectivity. By use of chiral oxygen-containing aldehydes, operationally simple access to aminohydroxylated polyketide substructures is possible. The results of catalyst-free, decarboxylative Mannich reactions of enolizable imines are described. When the reaction is performed with imines obtained from chiral aldehydes, access to optically pure Mannich products is possible. Copyright
- Boehm, Maximillian,Proksch, Kerstin,Mahrwald, Rainer
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supporting information
p. 1046 - 1049
(2013/03/14)
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- Entirely green protocol for the synthesis of β-aminoketones using saccharose as a homogenous catalyst
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Saccharose was applied as an efficient and homogenous catalyst for a one-pot, three-component Mannich reaction for the formation of β-aminoketones from aromatic aldehydes, anilines, and acetophenone at ambient temperature in excellent yields. This protocol has the following advantages: mild conditions, high yields, clean reaction profiles, operational simplicity, and environmentally benign and simple work-up procedures.
- Mousavi, Mir Rasul,Hazeri, Nourallah,Maghsoodlou, Malek Taher,Salahi, Sajjad,Habibi-Khorassani, Sayyed Mostafa
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p. 411 - 414
(2013/07/19)
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- Bi(NO3)3·5H2O: An efficient and green catalyst for synthesis of 1,5-benzodiazepines and β-amino carbonyl compounds
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Bismuth nitrate pentahydrate is found to be an efficient catalyst for the synthesis of 1,5-benzodiazepines and β-amino carbonyl compounds using condensation of o-phenylenediamine with ketones and one pot three component Mannich reaction, respectively under solvent free conditions at room temperature. This method offers a simple, solvent free, room temperature, environment friendly synthesis of 1,5-benzodiazepines and β-amino carbonyl compounds. The products are isolated by column chromatography and recrystallization, respectively and were characterized by their melting point, IR and 1H NMR spectroscopy.
- Rajput, Jaspreet Kaur,Kaur, Gagandeep
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p. 6545 - 6549
(2013/07/26)
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- Solvent and catalyst free azo-Michael addition under high-speed vibration milling
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Under the high-speed vibration milling conditions, the solvent and catalyst-free azo-Michael addition of chalcone derivatives and amines was found to proceed efficiently in excellent yields at ambient temperature in short reaction time. In most cases, con
- Li, Yu Jin,Cao, Yong Wen,Xu, Feng Shuang,Fang, Wen Ming,Yu, Wu Bin,Jia, Jian Hong,Gao, Jian Rong
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p. 1252 - 1256
(2012/10/29)
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- K3PO4-catalyzed one-pot synthesis of β-amino ketones
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A new strategy which uses cheap K3PO4 as a very effective catalyst has been developed for synthesis of β-amino ketones by one-pot reaction of an aryl aldehyde, acetophenone derivative, and amine in EtOH at room temperature. Springer-Verlag 2012.
- Movassagh, Barahman,Khosousi, Sakineh
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p. 1503 - 1506
(2013/02/21)
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- Highly efficient one-pot, three-component synthesis of β-aminoketones catalyzed by Fe(O2CCF3)3
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(Chemical Equation Presented) A highly efficient one-pot, three-component synthesis of β-aminoketones was demonstrated using the cost-effective, noncorrosive, and easily available Fe(O2CCF3)3 as a catalyst for the first time. The method can be employed to synthesize a wide range of target compounds and to introduce different functional groups into the β-aminoketone skeleton. Additionally, the method consistently has the advantages of good yields, short reaction time, and simply experimental workup procedure, which makes it a useful process for the synthesis of functionalized β-aminoketones. Copyright Taylor & Francis Group, LLC.
- Zhang, Min,Xiong, Biao,Yang, Wei,Chen, Ling,Wu, Feng,Wang, Quan,Ding, Yuqiang
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experimental part
p. 2831 - 2843
(2012/07/27)
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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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- PEG-OSO3H as an efficient and recyclable catalyst for the synthesis of β-amino carbonyl compounds via the Mannich reaction in PEG-H2O
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Sulfuric acid-modified polyethylene glycol 6000 (PEG-OSO3H) was applied as an efficient and recyclable catalyst for the synthesis of β-amino carbonyl compounds via the Mannich reaction between aldehydes, aromatic ketones and aromatic amines at room temperature using PEG400-H 2O (1:1) as environment-friendly solvents. The reactions were completed in short times and mild reaction conditions with good to excellent yields.
- Wang, Xi Cun,Zhang, Li Jia,Zhang, Zhang,Quan, Zheng Jun
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experimental part
p. 423 - 426
(2012/05/20)
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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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- Guanidine-based task-specific ionic liquids as catalysts for aza-Michael addition under solvent-free conditions
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An efficient and facile protocol for aza-Michael addition of aliphatic and aromatic amines to electron-deficit alkenes using [TMG][Lac] as catalyst under solvent-free conditions was established.
- Ying, Anguo,Zheng, Ming,Xu, Haidan,Qiu, Fangli,Ge, Changhua
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experimental part
p. 883 - 890
(2012/04/17)
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- One-pot three-component Mannich-type reaction catalyzed by trifluoromethanesulfonic acid in water
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One-pot three-component Mannich-type reaction of ketones, aldehydes and amines was efficiently catalyzed by liquid trifluoromethanesulfonic acid in water at ambient temperature. The high yield of corresponding β-amino ketones compounds were achieved. The proposed method is mild, green, simple and efficient.
- Li, Gang,Wu, Hankui,Wang, Zhiyong,Wang, Xianli
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experimental part
p. 89 - 93
(2011/05/30)
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- Bis[(L)prolinato-N,O]Zn in acetic acid-water: A novel catalytic system for the synthesis of β-amino carbonyls via Mannich reaction at room temperature
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Zn[(L)proline]2 was used as an efficient catalyst for the one-pot multicomponent reactions (MCR) of different aromatic amines, aromatic aldehyde and ketones in aqueous media. This method provides a novel and improved method for obtaining stereoselective β-amino carbonyl compounds in terms of good yield. Little catalyst loading, recyclability, easy accessibility of the catalyst and aqueous media are the main features of this protocol. Moreover column chromatography and recrystallization of product are not required as the crude product itself is very pure. Powder XRD and TEM images of the catalyst were taken for the first time.
- Kidwai, Mazaahir,Jain, Arti,Poddar, Roona,Bhardwaj, Saurav
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experimental part
p. 335 - 340
(2012/05/04)
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- Highly efficient Fe(HSO4)3-catalyzed one-pot mannich-type reactions: Three component synthesis of β-amino carbonyl compounds
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Fe(HSO4)3-catalyzed three-component one-pot Mannich reaction of acetophenone with different aromatic aldehydes and aromatic amines in ethanol at ambient temperature afforded the corresponding β-aminocarbonyl compounds in very good to excellent yields. Short reaction time, excellent yield, easy work-up procedure, applicability of using various amines and aldehydes, capability of conversion of ortho-substituted aromatic amines to the corresponding Mannich base in satisfying yields, and eventually high reusability of the catalyst show the merit of this study. Copyright Taylor & Francis Group, LLC.
- Eshghi, Hossein,Alipour, Afsaneh,Damavandi, Saman
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experimental part
p. 266 - 271
(2011/06/26)
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- Aluminium dodecatungstophosphate (AlPW12O40)-An efficient catalyst for three-component Mannich reaction in water
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One-pot, three-component Mannich reactions of ketones, aldehydes and amines were efficiently catalyzed by AlPW12O40 in water at ambient temperature to give the corresponding β-amino ketones in good to excellent yields. The method has the following merits: Firstly, Catalyst AlPW12O40 is non-corrosive and environmentally benign; Secondly, loading amount of catalyst is very low, less than 1 mol %; Thirdly, water as solvent is green and safe.
- Li, Gang,Long, Ruiling,Yang, Suling,Zhang, Liping
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experimental part
p. 559 - 563
(2011/10/31)
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- SnCl45H2O-catalyzed synthesis of β-amino carbonyl compounds via a direct Mannich-type reaction
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An efficient three-component, one-pot synthesis of β-amino carbonyl compounds from aromatic ketones, aromatic aldehydes, and aromatic amines using tin tetrachloride at room temperature in ethanol is described. The advantages of the new method are good yields (62-96%), simple workup, and inexpensive catalyst. Copyright Taylor & Francis Group, LLC.
- Wang, Min,Song, Zhiguo,Liang, Yan
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experimental part
p. 1 - 6
(2011/12/22)
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- Aromatic compounds Mannich reaction using economical acidic ionic liquids based on morpholinium salts as dual solvent-catalysts
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Economical acidic ionic liquids containing an alkanesulfonic acid group in a morpholinium cation were found to be effective catalysts for the Mannich reactions of various kinds of aromatic aldehydes, acetophenone and aromatic amines at mild reaction conditions. The satisfactory results were obtained with short reaction time, good yields of the Mannich bases and simplicity in the experimental procedure. These ionic liquids could be recycled and reused for up to five times without considerable decreasing in the catalytic activity. Copyright
- Yue, Caibo
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experimental part
p. 3640 - 3647
(2010/12/25)
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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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- CeCl3·7H2O as an efficient catalyst for one-pot synthesis of β-amino ketones by three-component Mannich reaction
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Cerium trichloride heptahydrate (CeCl3·7H2O) was found to be an efficient and recyclable catalyst for the three-component direct Mannich reaction of anilines and benzaldehydes with acetophenone. This protocol has advantages of high yield, no environmental pollution, mild condition, and simple work-up procedure.
- Dai, Yan,Li, Bin Dong,Quan, Heng Dao,Lü, Chun Xu
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experimental part
p. 31 - 34
(2010/11/04)
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- Three component one pot synthesis of β-amino ketones mediated by (bromodimethyl)sulfonium bromide
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A convenient one pot three component Mannich reaction of acetophenones with aromatic aldehydes and anilines catalysed by (bromodimethyl)sulfonium bromide under solvent free conditions at ambient temperature affording the corresponding β-amino ketones in good yields is described.
- Shailaja,Manjula,Rao, B. Vittal
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experimental part
p. 482 - 486
(2010/10/19)
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- Aluminium nitrate as an efficient and reusable catalyst for the three components one-pot Mannich reaction: Synthesis of β-amino carbonyl compounds
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Three components one-pot Mannich reaction of aromatic ketones, aromatic aldehydes and aromatic amines has been efficiently catalysed by recyclable aluminium nitrate at ambient temperature to give various β-amino carbonyl compounds in high yields. By simple phase separation, aluminium nitrate could be recycled several times without distinct loss of activity.
- Wang, Min,Liang, Yan,Song, Zhiguo
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supporting information; experimental part
p. 1653 - 1656
(2011/02/21)
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- Aza-Michael addition of aliphatic or aromatic amines to α,β-unsaturated compounds catalyzed by a DBU-derived ionic liquid under solvent-free conditions
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A task-specific ionic liquid, 1,8-diazabicyclo[5.4.0]-undec-7-en-8-ium acetate has been successfully used as a catalyst for aza-conjugate addition of aliphatic or aromatic amines to various electron deficient alkenes under solvent-free conditions and at room temperature. The catalyst can be reused for six times without noticeable loss of activity.
- Ying, An-Guo,Liu, Luo,Wu, Guo-Feng,Chen, Gang,Chen, Xin-Zhi,Ye, Wei-Dong
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scheme or table
p. 1653 - 1657
(2009/06/28)
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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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- Pronounced catalytic effect of a micellar solution of sodium dodecylsulfate (SDS) upon a three-component reaction of aldehydes, amines, and ketones under neutral conditions
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A micellar solution of anionic, cationic or neutral surfactants can be used as an excellent medium for three-component Mannich reactions of aldehydes, amines, and ketones at room temperature. Sodium dodecylsulfate turned out to efficiently catalyze the reaction in neutral pure water (pH ≈ 7), and the corresponding desired β-amino ketones precipitate while the reactions proceedes. This method provides a novel and improved modification of the three-component Mannich reaction in terms of mild reaction conditions, clean reaction profile, improved yields, and excellent regio- and diastereoselectivities with a simple workup. Interesting examples of click chemistry under neutral conditions in water were observed. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.
- Jafari, Abbas Ali,Moradgholi, Fatemeh,Tamaddon, Fatemeh
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experimental part
p. 1249 - 1255
(2009/08/09)
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- Bismuth(III) chloride-catalyzed one-pot Mannich reaction: three-component synthesis of β-amino carbonyl compounds
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A simple and efficient method has been developed for the one-pot Mannich reaction of β-amino carbonyl compounds from aromatic aldehydes, aromatic ketones and aromatic amines in the presence of a catalytic amount of bismuth trichloride.
- Li, Hua,Zeng, Hong-yao,Shao, Hua-wu
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scheme or table
p. 6858 - 6860
(2010/05/03)
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- SnCl2-catalyzed three-component one-pot Mannich-type reaction: Efficient synthesis of β-aminocarbonyl compounds
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SnCl2-catalyzed three-component one-pot Mannich reaction of acetophenone or p-chloroacetophenone with different aromatic aldehydes and aromatic amines in ethanol at ambient temperature gave the corresponding β-aminocarbonyl compounds in good to excellent yields. Four new compounds are reported for the first time.
- Wang, Min,Song, Zhi-Guo,Wan, Xin,Zhao, Suang
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experimental part
p. 1205 - 1208
(2011/10/05)
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- High stereoselective Mannich reaction catalyzed by Starch sulfonic acid in water
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Starch sulfonic acid was used as efficient and highly stereoselective catalyst for the three-component Mannich reaction of aldehydes, amines, and ketones in water at ambient temperature to afford the corresponding β-amino ketones in good to excellent stereoselectivity and yields.
- Wan, Yu,Lin, Wei,Chen, Xiu-Mei,Shen, Yang,Xin, Hai-Qiang,Xu, Hua-Hong,Yuan, Rui,Pang, Li-Ling,Ma, Rui,Yue, Cai-Hui,Yin, Wei,Bo, Rong-Cheng,Wu, Hui
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experimental part
p. 456 - 461
(2010/04/23)
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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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- 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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