- Synthesis and structure of 1-ethyl-2,4,5-triphenyl-1H-imidazole (Ethyl-Lophine)
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Ethyl-Lophine, 1-ethyl-2,4,5-triphenyl-1H-imidazole, C23H 20N2, was synthesized as a precursor for large organic cations in ionic liquids using an improved microwave-assisted method. The title compound and a precursor compound were characterized by NMR, IR, and DSC thermal measurements, as well as elemental analyses. The crystal structure of ethyl-lophine was determined by singlecrystal X-ray structure analysis (triclinic, P1, a = 10:1137(3), b = 12:4935(4), c = 14:6351(4) A, α = 98:182(2), β = 90:694(2), γ = 102:666(2), Z = 4, wR2 = 0:1030 for 611 refined parameters).
- Peppel, Tim,Koeckerling, Martin
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- Ag–TiO2 nanocomposite-catalyzed one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles: a green and benign approach
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Ag–TiO2 nanocomposite as an efficient catalyst was synthesized and characterized by AFM analysis. This nanocomposite acts as a heterogeneous and recyclable catalyst for the room temperature synthesis of 1,2,4,5-tetrasubstituted imidazoles from aldehydes, benzil, ammonium acetate and several anilines or aliphatic amines via one-pot four-component condensation reaction in H2O as a green solvent. Ag–TiO2 nanocomposite was simply recovered by filtration and was reused up to three times.
- Alipour, Soghra,Vahdat, Seyed Mohammad,Chekin, Fereshteh
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p. 2315 - 2321
(2021/05/27)
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- Tri(1-butyl-3-methylimidazolium) gadolinium hexachloride, ([bmim]3[GdCl6]), a magnetic ionic liquid as a green salt and reusable catalyst for the synthesis of tetrasubstituted imidazoles
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The magnetic ionic liquid, tri(1-butyl-3-methylimidazolium) gadolinium hexachloride, ([bmim]3[GdCl6]), has been used as an efficient green catalyst for the one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles via the condensation of benzil, an aromatic aldehyde, aniline, and ammonium acetate. Good to excellent yield, mild reaction conditions, as well as ease of operation and work-up are some advantages of the protocol.
- Akbari, Ali
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supporting information
p. 431 - 434
(2016/01/12)
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- SbCl5.SiO2: An efficient alternative for one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles in solvent or under solvent-free condition
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In a one-pot four-component reaction, an aldehyde, an amine, benzil and ammonium acetate were condensed for the synthesis of 1,2,4,5-tetrasubstituted imidazoles in the presence of silica supported antimony pentachloride (SbCl 5.SiO2) in improved yields. The catalyst is recoverable by simple filtration and can be used in the subsequent reactions.
- Sadeghi,Mirjalili,Bidaki,Ghasemkhani
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experimental part
p. 648 - 652
(2012/07/14)
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- Efficient multi-component synthesis of highly substituted imidazoles utilizing P2O5/SiO2 as a reusable catalyst
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Phosphorus pentoxide supported on silica gel (P2O 5/SiO2) has been used as an efficient and reusable catalyst for the one-pot pseudo four-component synthesis of 2,4,5-trisubstituted imidazoles from benzil or benzoin, aldehydes, and ammonium acetate. It was also used for four-component preparation of 1,2,4,5-tetrasubstituted imidazoles from benzil or benzoin, aldehydes, primary amine, and ammonium acetate under thermal solvent-free conditions. The remarkable features of this new procedure are high conversions, cleaner reaction, simple experimental and work-up procedures and also the catalyst can be easily separated from the reaction mixture and reused several times without any loss of its activity.
- Shaterian, Hamid Reza,Ranjbar, Mohammad,Azizi, Kobra
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experimental part
p. 1635 - 1645
(2012/01/06)
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- Synthesis of highly substituted imidazoles using Bronsted acidic ionic liquid, triphenyl(propyl-3-sulphonyl)phosphonium toluenesulfonate, as reusable catalyst
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Bronsted acidic ionic liquid, triphenyl(propyl-3-sulphonyl) phosphonium toluenesulfonate, has been used as an efficient and reusable catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles under solvent-free conditions in excellent yields.
- Shaterian,Ranjbar,Azizi
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experimental part
p. 1120 - 1134
(2012/02/04)
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- An environmental friendly approach for the synthesis of highly substituted imidazoles using Br?nsted acidic ionic liquid, N-methyl-2-pyrrolidonium hydrogen sulfate, as reusable catalyst
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Br?nsted acidic ionic liquid, N-methyl-2-pyrrolidonium hydrogen sulfate, has been used as an efficient and reusable catalyst for the one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles under thermal solvent-free conditions in excellent yields.
- Shaterian, Hamid Reza,Ranjbar, Mohammad
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experimental part
p. 40 - 49
(2012/03/09)
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- A facile multicomponent synthesis of tetrasubstituted imidazoles using Fe3+-K10 catalyst under solvent-free microwave conditions
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An efficient, microwave assisted, multi-component synthesis of 1,2,4,5-tetrasubstituted imidazoles has been achieved by the one-pot condensation of benzil, aromatic aldehyde, aliphatic/aromatic amine and ammonium acetate using Fe3+-K10 heterogeneous catalyst under solvent-free conditions. This approach offers a number of advantages such as excellent yield, solvent-free conditions, short reaction time, an eco-friendly and low loading catalyst, mild reaction temperature, and an easy work-up.
- Raghuvanshi,Singh, Krishna Nand
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experimental part
p. 1394 - 1397
(2011/01/13)
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- BF3·SiO2: an efficient reagent system for the one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles
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Silica-supported boron trifluoride (BF3·SiO2) is an efficient, readily available and reusable catalyst for the synthesis of 1,2,4,5-tetrasubstituted imidazoles using benzil, an aromatic aldehyde and an amine in the presence of ammonium acetate. This one-pot procedure is very simple, affording good to excellent yields.
- Sadeghi, Bahareh,Mirjalili, Bi Bi Fatemeh,Hashemi, Mohammad M.
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p. 2575 - 2577
(2008/09/21)
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- An efficient and one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed by InCl3·3H2O
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InCl3·3H2O was found to be a mild and effective catalyst for the efficient, one-pot, three component synthesis of 2,4,5-trisubstituted imidazoles at room temperature. Moreover, the utility of this protocol was further explored conveniently for the one-pot, four component synthesis of 1,2,4,5-tetrasubstituted imidazoles in high yields.
- Das Sharma, Saikat,Hazarika, Parasa,Konwar, Dilip
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p. 2216 - 2220
(2008/09/18)
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- N-alkylation of 2,4,5-triphenyl imidazole derivatives using a new phase transfer reagent under PTC conditions
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The phase transfer catalyzed N-alkylation of 2,4,5-triphenyl imidazole derivatives using a new phase transfer reagent namely, 2-benzilidine-N,N,N,N′,N′,N′-hexaethyl propane-1,3-diammonium dibromide have been described. The structures of all the 14 compounds have been established by spectroscopic means.
- Jayachandran,Wang
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p. 2743 - 2752
(2007/10/03)
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- Syntheses and analgesic activities of some 2-substituted-4,5-diphenyl and 1,2-disubstituted-4,5-diphenyl imidazole derivatives
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Some substituted imidazole compounds were synthesized and their analgesic activities were determined on the Swiss albino mice (25-35 g) of either sex. During the synthesis, 2-substituted-4,5-diphenyl imidazole compounds were obtained by the reaction of benzil with some substituted or nonsubstituted aldehyde derivatives, in the presence of ammonium acetate. 1- Ethyl-2-substituted-4,5-diphenyl imidazole compounds were obtained by the reaction of purified 2-substituted-4,5-diphenyl imidazole derivatives with alkyl halides in THF at the presence of NaH. All spectral and elemental analyses of the compounds were completed and their structures elucidated. Analgesic activities of the compounds were examined using the Tail-Clip method. 15a (2-p-chlorophenyl-4,5-diphenyl imidazole) and 6b (1-ethyl-2-p- hydroxyphenyl-4,5-diphenyl imidazole) derivatives were found to be more active than the others and their LD50 values were found to be greater than 100 mg/kg (i.p.).
- Isikdag,Meric
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- Photochemistry of N-heterocycles, 5: A comparison of chemical and photochemically induced reduction of some 2(4),5-dihydro-1,2,4-triazines and aromatic 1,2,4-triazines
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Chemical reduction (Zn/AcOH) of the arene 1 and of 2(4),5-dihydro-1,2,4- triazine 7 has been reinvestigated, resulting in the amendment of literature data concerning this reaction. Chemical, electrochemical, and photochemically induced reductions and ring contractions of 1,2,4-triazine derivatives have been compared. The first example of a triaryl-1,4-dihydrotriazine has been prepared. Some further evidence is presented that supports the proposed mechanism of the photochemically induced reduction and ring contraction of 1,2,4-triazines.
- Nagy, Jozsef,Horvath, Aniko,Szoelloesy, Aron,Nyitrai, Jozsef
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p. 685 - 689
(2007/10/03)
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- PRODUCTS FROM REACTION OF BENZALDEHYDE THIOSEMICARBAZONE WITH POTASSIUM ETHOXIDE
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When heated with potassium ethoxide, benzaldehyde thiosemicarbazone gives a mixture of 2,4,5-triphenylimidazole, hydrazodithioformamide, benzoic acid, and benzaldehyde oxime.It was shown that these compounds are formed through the intermediate benzaldehyde azine and benzonitrile.
- Marshalkin, M. F.,Yakhontov, L. N.
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p. 2273 - 2276
(2007/10/02)
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