- Synthesis, characterization and crystal structure of (2Z)-3-[(4- methylphenyl)amino]-1-phenylbut-2-en-1-one
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The compound (2Z)-3-[(4-methylphenyl)amino]- 1-phenylbut-2-en-1-one was synthesized by the condensation reaction of benzoylacetone with p-methylaniline and structurally characterized by 1H NMR, 13C NMR, IR, mass spectrometry, element
- Patil, Siddappa A.,Gonzalez-Flores, Diego,Medina, Phillip A.,Vohs, Jason K.,Dever, Seth,Popp, Joshua,Stentzel, Michael,Pineda, Leslie W.,Montero, Mavis L.,Fahlman, Bradley D.
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- A Reusable CNT-Supported Single-Atom Iron Catalyst for the Highly Efficient Synthesis of C?N Bonds
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C?N bond formation is regarded as a very useful and fundamental reaction for the synthesis of nitrogen-containing molecules in both organic and pharmaceutical chemistry. Noble-metal and homogeneous catalysts have frequently been used for C?N bond formatio
- Baell, Jonathan B.,Ding, Qifeng,Huang, Fei,Huang, He,Xu, Mingjie,Yu, Yang,Zhang, Lihui,Zheng, Jian-Guo
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supporting information
(2020/03/24)
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- Nano-SiO2 catalyzed synthesis of β-enaminones under solvent free conditions
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Nano-SiO2 efficiently catalyzed the synthesis of β-enaminones using direct condensation of various (cyclic and acyclic) β-diketones with aromatic and aliphatic amines under solvent-free conditions. This eco-friendly catalyst can be recovered and reused without significant loss of activity. This methodology provides a simple synthetic route to enaminones in excellent yields at room temperature. Graphical abstract: [Figure not available: see fulltext.]
- Alinezhad, Heshmatollah,Tajbakhsh, Mahmood,Sarkati, Malihe Norouzi,Zare, Mahboobe
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p. 1591 - 1596
(2016/08/16)
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- Solvent-free synthesis of β-enamino ketones and esters catalysed by recyclable iron(III) triflate
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A novel application of highly stable Fe(OTf)3 as an efficient catalyst for the synthesis of a variety of β-enamino ketones and esters under solvent-free conditions is described. Notably, this protocol of a "green synthesis", which produced β-enamino ketones and esters by the reaction of a variety of β-dicarbonyl compounds and primary amines, exhibits attractive properties including high yields, short reaction periods, lower loading of catalyst and chemo- and regio-selectivity. In addition, the catalyst was easily recovered from the reaction system and readily reused with minimal loss of activity.
- Feng, Cheng-Liang,Chu, Ning-Ning,Zhang, Shu-Guang,Cai, Jin,Chen, Jun-Qing,Hu, Hua-You,Ji, Min
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p. 1097 - 1103
(2014/05/20)
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- Zinc triflate catalysed synthesis of β-enamino ketones(esters) under solvent-free conditions
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An efficient and mild procedure is described for the synthesis of a series of β-enamino ketones(esters) from 1,3-dicarbonyl compounds and aliphatic and aromatic amines using zinc triflate as the catalyst.
- Feng, Chengliang,Zhang, Shuguang,Cai, Jin,Chen, Junqing,Hu, Huayou,Ji, Min
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p. 626 - 629
(2013/11/06)
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- Formic acid: A low-cost, mild, ecofriendly, and highly efficient catalyst for the rapid synthesis of β-enaminones
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β-Enaminones have been synthesized by the condensation reaction of b-diketones with various anilines in the presence of a catalytic amount of formic acid, mild and highly efficient acid catalyst in methanol. These condensation reactions proceed smoothly in short reaction times with near-quantitative yields. Copyright
- Patil, Siddappa A.,Medina, Phillip A.,Gonzalez-Flores, Diego,Vohs, Jason K.,Dever, Seth,Pineda, Leslie W.,Montero, Mavis L.,Fahlman, Bradley D.
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p. 2349 - 2364
(2013/07/26)
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- Silica supported Fe(HSO4)3 as an efficient, heterogeneous and recyclable catalyst for synthesis of β-enaminones and β-enamino esters
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A series of β-substituted enaminones were prepared through the one-pot reaction of β-dicarbonyl compounds with various amines in the presence of silica ferric hydrogensulfate under solvent free conditions at room temperature. The reactions proceed smoothl
- Eshghi, Hossein,Seyedi, Seyed Mohammad,Safaei, Elham,Vakili, Mohammad,Farhadipour, Abolghasem,Bayat-Mokhtari, Mohtaram
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p. 430 - 436
(2012/10/30)
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- Synthesis and characterisation of bis(β-ketoaminato) complexes of cobalt(ii)
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Condensation of 1-phenyl-1,3-butanedione with various substituted anilines affords N-aryl substituted β-ketoamines PhC(O)CHC(CH3)Naryl, which, when deprotonated and reacted with Co(OAc)2·4H 2O yields a series of bis(β-keto
- Robson, Kiyoshi C. D.,Phillips, Cory D.,Patrick, Brian O.,McNeil, W. Stephen
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experimental part
p. 2573 - 2578
(2010/05/15)
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- Solid-state synthesis of β-enamino ketones from solid 1,3-dicarbonyl compounds and ammonium salts or amines
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A facile amination of solid 1,3-dicarbonyl compounds with ammonium salts or amines in solid state has been achieved by mechanochemical grinding in the presence of KHSO4 and SiO2. Most of the reactions proceed smoothly at room temperature under solid-state conditions and give their corresponding β-imino derivatives in high yields. The method has the advantage of simple manipulation and mild conditions. Georg Thieme Verlag Stuttgart.
- Xu, Shi-Liang,Li, Cheng-Ping,Li, Jing-Hua
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experimental part
p. 818 - 822
(2009/07/18)
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- A mild method for the synthesis of β-enaminones and β-enamino esters using KH2P04 as catalyst
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β-Enaminones and β-enamino esters have been produced by the direct condensation of amines with β-diketones and β-ketoesters using KH2P04 as catalyst under mild, solvent-free conditions.
- Xu, Feng,Lv, Hong-Xia,Wang, Jin-Ping,Tian, You-Ping,Wang, Jian-Jun
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experimental part
p. 707 - 710
(2009/10/02)
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- Enamination of β-dicarbonyl compounds with amines
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Enamination of a wide variety of primary amines was successfully described with excellent chemoselectivity in the presence of catalytic amounts of β-cyclodextrin in water under mild conditions. Aliphatic amines also reacted efficiently to produce the corresponding enaminones.
- Khodaei,Khosropour,Cardel
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scheme or table
p. 217 - 221
(2009/04/06)
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- A novel enamination of β-dicarbonyl compounds catalyzed by Bi(TFA)3 immobilized on molten TBAB
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Enamination of a wide variety of primary amines was successfully carried out in the presence of catalytic amounts of bismuth(III) trifluoroacetate immobilized on molten tetrabutylammonium bromide as "green" media under mild conditions. This new system of the catalyst is recyclable and reusable. Generally, the results of the reaction in tetrabutylammonium bromide is better than the previously obtained results in water because of their yields and reaction times.
- Khodaei, Mohammad M.,Khosropour, Ahmad R.,Kookhazadeh, Mehdi
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p. 209 - 212
(2007/10/03)
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- Cerium(III) chloride heptahydrate (CeCl3·7H2O) as an efficient enamination catalyst in aqueous media
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Cerium(III) chloride heptahydrate CeCl3·H2O catalyzes enamination of β-dicarbonyl compounds with primary amines in aqueous medium at room temperature to afford the corresponding β-enamino ketones with high chemoselectivity.
- Khodaei,Khosropour,Kookhazadeh
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p. 1445 - 1448
(2007/10/03)
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- A mild, efficient and environmentally friendly method for the regio- and chemoselective synthesis of enaminones using Bi(TFA)3 as a reusable catalyst in aqueous media
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Bismuth(III) trifluoroacetate has been found to be an extremely efficient catalyst for the preparation of β-enaminones in water. In addition, by employing this catalyst, high regio- and chemoselective enamination of carbonyl compounds was achieved.
- Khosropour, Ahmad R.,Khodaei, Mohammad M.,Kookhazadeh, Mehdi
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p. 1725 - 1728
(2007/10/03)
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- Enamination of β-dicarbonyl compounds catalyzed by CeCl 3·7H2O at ambient conditions: Ionic liquid and solvent-free media
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Enamination of a wide various primary amines was successfully carried out in the presence of catalytic amounts of cerium chloride heptahydrate in ionic liquid and solvent-free conditions as 'green' media under mild reaction conditions.
- Khodaei, Mohammad Mehdi,Khosropour, Ahmad Reza,Kookhazadeh, Mehdi
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p. 1980 - 1984
(2007/10/03)
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- Deuterium isotope effects on 13C chemical shifts of enaminones
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Deuterium isotope effects on 13C chemical shifts have been studied in a series of substituted N-alkyl and N-phenyl keto-enamines. The intramolecularly hydrogen bonded Z-forms show the largest two-bond isotope effects, 2δC-1 (ND). Methyl-substitution at C-1 leads to a larger two-bond isotope effect in the N-phenyl-substituted derivatives. This effect is ascribed to steric compression. Space-filling substituents at the ortho-position of the N-phenyl ring lead to a decrease of the two-bond isotope effect. A correlation is found between 2δC-1(ND) and 3δC-2′(ND). The latter becomes negative in the sterically hindered cases. 3δC-2′(ND) may therefore be used as a gauge of the twist of the phenyl ring. o-Hydroxy substitution of the CO-phenyl rings enables intramolecular hydrogen bonding to the carbonyl group. This kind of hydrogen bond with two donors to one acceptor leads to smaller 2δC-2(ND) and 2δC-2″(OD) isotope effects equivalent to weaker hydrogen bonds for the Z-isomer. This is ascribed to competition for the acceptor. For the E-isomer 2δC(OD) is enhanced. The same feature is seen for N,N-dimethylamino enamines. This increase is ascribed to delocalization of the nitrogen lone-pair onto the carbonyl oxygen, thereby strengthening the hydrogen bond and thus leading to larger two-bond, 2δC(OD), isotope effects. Acta Chemica Scandinavica 1997.
- Zheglova, Donka Kh.,Genov, Daniel G.,Bolvig, Simon,Hansen, Poul Erik
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p. 1016 - 1023
(2007/10/03)
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