- Characterization and electronic spectral studies of 2-(naphthalen-1-yl)-4, 5-diphenyl-1H-imidazole bound Fe2O3 nanoparticles
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Multicomponent, one-pot, highly efficient, indium trifluoride (InF 3) catalytic synthesis of 2-(naphthalen-1-yl)-4,5-diphenyl-1H- imidazole under solvent-free condition is reported. Characterization of imidazole has been carried out by spectral
- Karunakaran,Jayabharathi,Kalaiarasi,Jayamoorthy
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- TMSOTf-catalyzed synthesis of trisubstituted imidazoles using hexamethyldisilazane as a nitrogen source under neat and microwave irradiation conditions
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In the process of drug discovery and development, an efficient and expedient synthetic method for imidazole-based small molecules from commercially available and cheap starting materials has great significance. Herein, we developed a TMSOTf-catalyzed synthesis of trisubstituted imidazoles through the reaction of 1,2-diketones and aldehydes using hexamethyldisilazane as a nitrogen source under microwave heating and solvent-free conditions. The chemical structures of representative trisubstituted imidazoles were confirmed using X-ray single-crystal diffraction analysis. This synthetic method has several advantages including the involvement of mild Lewis acid, being metal- and additive-free, wide substrate scope with good to excellent yields and short reaction time. Furthermore, we demonstrate the application of the methodology in the synthesis of biologically active imidazole-based drugs.
- Asressu, Kesatebrhan Haile,Chan, Chieh-Kai,Wang, Cheng-Chung
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p. 28061 - 28071
(2021/09/15)
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- Catalytic conversion of 2,4,5-trisubstituted imidazole and 5-substituted 1H-tetrazole derivatives using a new series of half-sandwich (η6-p-cymene)Ruthenium(II) complexes with thiophene-2-carboxylic acid hydrazone ligands
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A new series of half-sandwich (η6-p-cymene) ruthenium(II) complexes with thiophene-2-carboxylic acid hydrazide derivatives [Ru(η6-p-cymene)(Cl)(L)] [L = N'-(naphthalen-1-ylmethylene)thiophene-2-carbohydrazide (L1), N'-(anthracen-9-ylmethylene)thiophene-2-carbohydrazide (L2) and N'-(pyren-1-ylmethylene)thiophene-2-carbohydrazide (L3)] were synthesized. The ligand precursors and their Ru(II) complexes (1–3) were structurally characterized by spectral (IR, UV–Vis, NMR and mass spectrometry) and elemental analysis. The molecular structures of the ruthenium(II) complexes 1–3 were determined by single-crystal X-ray diffraction. All complexes were used as catalysts for the one-pot three-component syntheses of 2,4,5-trisubstitued imidazole and 5-substituted 1H-tetrazole derivatives. The catalytic studies optimized parameters as solvent, temperature and catalyst. The catalysts revealed very active for a broad range of aromatic aldehydes presenting either electron attractor or electron donor substituents and, although less active, moderate to high activities were observed for alkyl aldehydes.
- Vinoth, Govindasamy,Indira, Sekar,Bharathi, Madheswaran,Archana, Govindhasamy,Alves, Luis G.,Martins, Ana M.,Shanmuga Bharathi, Kuppannan
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- Simple practical method for synthesis of trisubstituted imidazoles: an efficient copper catalyzed multicomponent reaction
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A rapid practical process has been developed for synthesis of 2,4,5-trisubstituted-imidazoles in excellent yields up to 95% from readily available starting materials. In this CuI catalyzed synthesis, trisubstituted imidazoles were afforded in short reaction times, wherein the substrate scope is well explored with benzoin as well as benzil reacting with different aldehydes in the presence of ammonium acetate as the nitrogen source.
- Kadu, Vikas D.,Khadul, Siddheshwar P.,Kothe, Gokul J.,Mali, Ganesh A.
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p. 21955 - 21963
(2021/07/02)
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- Magnetic horsetail plant ash (Fe3O4@HA): a novel, natural and highly efficient heterogeneous nanocatalyst for the green synthesis of 2,4,5-trisubstituted imidazoles
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Horsetail plant ash (HA), as a natural source of mesoporous silica, has been prepared from the exposure of horsetail plant (Equisetum Arvense) to high temperature. In the present study, a new magnetically separable and also recoverable Fe3O4 nanoparticles were synthesized in the presence of natural horsetail plant ash (HA) as a support to result in Fe3O4@HA. FT-IR, XRD, TEM, SEM–EDX and VSM analysis were combined to characterize the morphology and structure of this novel synthesized nanocatalyst. This magnetically solid acid nanocatalyst showed an excellent catalytic activity for the synthesis of 2,4,5-trisubstituted imidazoles at room temperature in aqueous media. The procedure led to corresponding products in high to excellent yields and appropriate times. Additionally, this nanocatalyst can be easily recovered by a magnetic field and reused for six other consecutive reaction runs without noticeable loss of its catalytic efficiency. Based on this study, Fe3O4@HA is found to be an efficient, magnetically separable, recyclable, and green catalyst with natural source. Graphic abstract: In this work, horsetail plant ash was used as a natural source of mesoporous silica for the synthesis of Fe3O4@HA as a highly powerful magnetically solid acid nanocatalyst, which was fully characterized using various techniques. The activity of the newly synthesized nanocatalyst was tested for the synthesis of 2,4,5-trisubstituted imidazole derivatives.[Figure not available: see fulltext.]
- Hosseini Mohtasham, Nina,Gholizadeh, Mostafa
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p. 2507 - 2525
(2021/03/24)
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- NiO nanocomposites/rGO as a heterogeneous catalyst for imidazole scaffolds with applications in inhibiting the DNA binding activity
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Herein, we report a facile approach to synthesize a new highly versatile heterogeneous catalyst by spontaneous aerial oxidation based on nickel oxide nanocomposites immobilized on surface-functionalized reduced graphene oxide sheets. NiO nanocomposite/red
- Kumar, Gyanendra,Kumar, Manish,Masram, Dhanraj T.,Mogha, Navin Kumar,Subodh
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supporting information
p. 1963 - 1974
(2020/02/20)
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- New phosphonium molybdate-promoted green, fast and selective catalytic procedure for the synthesis of trisubstituted imidazoles
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The compound 1,1′-(ethane,1,2-diyl)ditriphenylphosphonium hexamolybdate dimethylsulfoxide {C2H4[P(C6H5)3]2}{Mo6O19}·SO (CH3)2 (I) was prepared, and 1H-NMR, 13C-NMR, Fourier transform-infrared, differential scanning calorimetry and single crystal X-ray diffraction analysis were used to characterize the titled compound. Crystallographic data showed that compound I crystallized in the monoclinic crystal system in C2/c space group. The compound (I) was used for selective synthesis of 2,4,5-tri aryl imidazole derivatives under solvent-free conditions efficiently. Because of hindrance of the catalyst, the yields of products for aldehydes bearing para substituents are higher than the aldehydes bearing ortho substituents, and for aromatic aldehydes with meta substituents are very low.
- Salmasi, Reihaneh,Gholizadeh, Mostafa,Salimi, Alireza
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- A new nanocomposite catalyst based on clay-supported heteropolyacid for the green synthesis of 2,4,5-trisubstituted imidazoles
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Intercalation of cetyltrimethylammonium (CTA+) cations within the nanolayers of montmorillonite (MMT) clay followed by reaction with Keggin-type phosphomolybdic acid (PMo) resulted in the synthesis of (CTA)3PMo-MMT nanocomposite catalyst. The prepared nanocomposite catalyst was characterized using different physicochemical methods such as Fourier-transform infrared and inductively coupled plasma–optical emission spectroscopies, X-ray diffraction, and nitrogen adsorption–desorption (Brunauer–Emmett–Teller method) analyses. Characterization techniques demonstrated the intercalation of (CTA)3PMo species into the nanolayers of MMT. The resulting (CTA)3PMo-MMT nanocomposite catalyst efficiently catalyzed the synthesis of 2,4,5-trisubstituted imidazoles under solvent-free conditions. The efficiency is due to the fact that the presence of CTA+ species makes the nanocomposite catalyst hydrophobic and facilitates the accessibility of hydrophobic reactants to active sites in the course of the reaction. High activity and selectivity were achieved in the presence of the prepared nanocomposite catalyst. The nanocomposite catalyst was readily isolated from the reaction mixture using simple filtration, washed with ethanol, and recycled five times without a major loss of activity.
- Masteri-Farahani,Ezabadi,Mazarei,Ataeinia,Shahsavarifar,Mousavi
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- Synthesis, antioxidant and α -amylase inhibition activity of naphthalene-containing 2,4,5-trisubstituted imidazole derivatives
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Abstract: A series of naphthalene ring containing 2,4,5-trisubstituted imidazole derivatives (2a–2l) were synthesized using one-pot multicomponent reaction. The reactions were carried out using naphthaldehyde and substituted benzil in the presence of ammo
- Somashekara,Thippeswamy,Vijayakumar
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- Simple, Efficient, and Convenient One-Pot Synthesis of Imidazole Derivatives in the Presence of Nanosilica-supported Imidazolium Ionic Liquid as a Catalyst
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An efficient and simple synthesis of 2,4,5-trisubstituted imidazoles is achieved by three-component cyclocondensation of benzil, aldehyde, and ammonium acetate by using nanosilica-supported imidazolium ionic liquid as a catalyst under solvent-free conditions. The key advantages of this process are high to excellent yields, short reaction time, easy work-up, and the reusability of the catalyst.
- Alinezhad, Heshmatollah,Alinezhad, Vajiheh,Mohseni Tavakkoli, Sahar
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p. 385 - 389
(2017/04/24)
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- Cobalt(II) catalyzed C(sp)-H bond functionalization of alkynes with phenyl hydrazines: Facile access to diaryl 1,2-diketones
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A cobalt acetylacetonate catalyzed oxidative diketonation of alkynes via C(sp)-H bond functionalization has been described. The reaction involves a free-radical mechanism, wherein the phenyl radical formed from phenyl hydrazine couples with Co(ii) activated alkyne to produce 1,2-diketones. The reaction proceeds at room temperature in DMF with the use of Ag2O/air as the oxidizing system. The utility of the protocol for the synthesis of a series of imidazoles including a potent platelet aggregation inhibitor trifenagrel has been demonstrated.
- Bharate, Jaideep B.,Abbat, Sheenu,Sharma, Rohit,Bharatam, Prasad V.,Vishwakarma, Ram A.,Bharate, Sandip B.
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p. 5235 - 5242
(2015/05/13)
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- An efficient green MCR protocol for the synthesis of 2,4,5-trisubstituted imidazoles by Selectfluor under ultrasound irradiation
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A simple, efficient and eco-friendly procedure has been developed using Selectfluor (15% mol) as a novel catalyst under ultrasound irradiation and solvent-free conditions for the synthesis of 2,4,5-triaryimidazole by a three-component, one-pot condensation of benzil, aryl aldehydes and ammonium acetate. The present methodology offers several advantages such as excellent yields, shorter reaction times (10-15 min) and environmentally benign milder reaction conditions and easy work-up.
- Heravi, Mohammad Reza Poor,Vessally, Esmaeil,Behbehani, Gholam R. Rezaei
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p. 146 - 150
(2014/03/21)
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- Synthesis of 2,4,5-triaryl and 1,2,4,5-tetraaryl imidazoles using silica chloride as an efficient and recyclable catalyst under solvent-free conditions
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An efficient solvent-free synthesis of various 2,4,5-triaryl imidazoles and 1,2,4,5-tetraaryl imidazoles has been developed using silica chloride as a heterogeneous catalyst. The present methodology offers several advantages, such as excellent yields, shorter reaction times, economic availability, and reusability of catalyst.
- Chavan, Hemant V.,Narale, Dattatraya K.
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p. 980 - 984
(2014/12/10)
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- Estimation of excited state dipolemoments from solvatochromic shifts-effect of pH
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Multicomponent, highly efficient, catalytic synthesis of some polysubstituted imidazole under solvent-free condition is reported. Characterization of polysubstituted imidazole have been carried out by X-ray diffraction (XRD) and spectral techniques. Electronic spectral studies reveal that their solvatochromic behavior depends not only on the polarity of the medium but also on the hydrogen bonding properties of the solvents. Specific hydrogen bonding interaction in polar solvents modulated the order of the two close lying lowest singlet states. The solvent effect on both the absorption and emission spectral results have been analyzed by multiple parametric regression analysis. Solvatochromic effects on the emission spectral position indicate the charge transfer (CT) character of the emitting singlet states both in a polar and a non polar environment. The fluorescence decays for the imidazole fit satisfactorily to a single exponential kinetics. The prototropic studies of N,N-dimethyl-4-(1,4,5-triphenyl-1H-imidazol-2-yl)naphthalen-1-amine (DTINA) reveal that two monocations [imidazole nitrogen protanated (MC1) and dimethylamino nitrogen protanated (MC2)] and a dication [both imidazole nitrogen and dimethylamino nitrogen protanated (DC)] are formed by protonation in both ground and excited states. These observations are in consistent with quantum chemical calculations.
- Jayabharathi,Kalaiarasi,Thanikachalam,Jayamoorthy
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p. 599 - 612
(2014/05/06)
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- Rapid access of some trisubstituted imidazoles from benzil condensed with aldehydes and ammonium acetate catalyzed by L-cysteine
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A simple highly versatile and efficient synthesis of 2,4,5- trisubstituted imidazole is achieved by three component cyclocondensation of benzil, substituted aromatic aldehyde and ammonium acetate by L-cysteine as organocatalyst under solvent free condition. The key advantages of this process are high yields, cost effectiveness catalyst, easy purification technique and above all environmentally benign.
- Roy,Rahman,Pramanick
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p. 153 - 159
(2013/02/25)
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- Highly efficient one-pot synthesis of trisubstituted imidazoles under catalyst-free conditions
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Operationally simple, atom economical, and scalable synthesis of 2,4,5-trisubstituted imidazoles from benzil, aldehydes, and ammonium acetate is shown to proceed readily in methanol with high yield. The scope of the reaction is quite broad; a variety of aromatic and aliphatic activated and unactivated aldehydes have all been shown to be viable substrates for this reaction. Excellent yields and purity were obtained by washing the products with hot ethanol.
- Azizi, Najmadin,Dado, Nairreh,Amiri, Alireza Khajeh
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experimental part
p. 195 - 198
(2012/03/07)
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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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- Synthesis of 2,4,5-triarylimidazoles in aqueous solution, under microwave irradiation
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A series of 2,4,5-triarylimidazoles was synthesized from a new, highly efficient and green method. The reaction is performed in water, without the presence of any catalyst, and under microwave irradiation. This provides new opportunities for the rapid scr
- Chauveau, Edouard,Marestin, Catherine,Schiets, Frederic,Mercier, Regis
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experimental part
p. 1018 - 1022
(2010/08/04)
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- Acidic ionic liquid [(CH2)4SO3HMIM] [HSO4]: A green media for the simple and straightforward synthesis of 2,4,5-trisubstituted imidazoles
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2,4,5-Trisubstituted imidazoles have been synthesized in excellent yields (85-95%) in the presence of 5mol% of [(CH2)4SO3HMIM] [HSO4] as a Brnsted acidic ionic liquid. Copyright
- Heravi, Majid M.,Zakeri, Masoumeh,Karimi, Narges,Saeedi, Mina,Oskooie, Hossien A.,Tavakoli-Hosieni, Niloofar
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experimental part
p. 1998 - 2006
(2010/09/06)
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- Potassium aluminum sulfate (alum): An efficient catalyst for the one-pot synthesis of trisubstituted imidazoles
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Trisubstituted imidazoles were synthesized in high yields in the presence of potassium aluminum sulfate (alum) as a non-toxic, reusable, inexpensive, and easily available reagent at 70°C.
- Mohammadi, Ali A.,Mivechi, Mersede,Kefayati, Hassan
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experimental part
p. 935 - 937
(2009/09/25)
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- Synthesis of 2,4,5-trisubstituted imidazoles catalyzed by [Hmim]HSO 4 as a powerful Broensted acidic ionic liquid
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An efficient and green procedure for the synthesis of 2,4,5-trisubstituted imidazoles with various aldehydes using a catalytic amount of 1-methylimidazolium hydrogenesulfate as an active and low cost Broensted acidic room temperature ionic liquid has been developed. The ionic liquid was easily separated from the reaction mixture and was recycled five times without any loss in activity.
- Khosropour, Ahmad R.
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p. 264 - 269
(2008/09/19)
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- Hypervalent iodine-mediated efficient synthesis of imidazoles
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The condensation of an α-hydroxy ketone with an aldehyde and ammonium acetate in the presence of diacetoxy iodobenzene (DIB) produced the corresponding imidazole in excellent yield. Copyright
- Das, Biswanath,Srinivas, Yallamalla,Holla, Harish,Krishnaiah, Maddeboina,Narender, Ravirala
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p. 1270 - 1271
(2008/03/13)
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