1965-19-1Relevant academic research and scientific papers
An Imidazole based probe for relay recognition of Cu2+ and OH- ions leading to and logic gate
Kaur, Navneet,Alreja, Priya
, p. 1253 - 1259 (2015)
2-(2-methoxyphenyl)-4,5-diphenyl-1H-imidazole 1, an imidazole-based compound, was found to sense Cu2+ ions via fluorescence and absorption spectroscopy over a number of other metal ions. During Cu2+ sensing, the chemosensor 1 followed a "switch-off" mechanism. Job's plot supported 1:1 stoichiometry of 1-Cu2+ complex. The 1-Cu2+ complex formed in situ underwent different absorption changes with OH- ions. These differential absorption changes observed with the addition of Cu2+ and OH- ions were used to mimic AND logic gate using A274nm as output. [Figure not available: see fulltext.]
A green and simple method for the synthesis of 2,4,5-trisubstituted-1H-imidazole derivatives using acidic ionic liquid as an effective and recyclable catalyst under ultrasound
Ahmed, N. Sh.,Hanoon
, p. 4083 - 4100 (2021/06/25)
Abstract: In the current work, an acidic ionic liquid ([{(IMC)-4-OMBH}BIM][HSO4]3) has been utilized as an effective and recyclable catalyst for the synthesis of 2,4,5-trisubstituted-1H-imidazole derivatives with high yields under optimal reaction conditions and ultrasound irradiation. Important features of the new catalyst are facile synthesis, cheap reagents and successful reuse for many times. What makes the present method an effective contribution in the field of synthesis of 2,4,5-trisubstituted-1H-imidazole derivatives is the fact that it can be described as environmentally friendly, economical, short reaction time, possible recover of the catalyst, simple workup, safer and mild reaction conditions. Graphic abstract: [Figure not available: see fulltext.].
Magnetic nanoparticle-supported sulfonic acid as a green catalyst for the one-pot synthesis of 2,4,5-trisubstituted imidazoles and 1,2,4,5-tetrasubstituted imidazoles under solvent-free conditions
Amoozadeh, Ali,Kolvari, Eskandar,Sakhdari, Mahnaz
, p. 71 - 78 (2021/10/30)
In this work, magnetic nanoparticle-supported sulfonic acid (γ-Fe2O3-SO3H) is used as an efficient catalyst in the synthesis of 2,4,5-trisubstituted imidazoles and 1,2,4,5-tetrasubstituted imidazoles in a short time (40-70 min for trisubstituted imidazoles and 30-40 min for tetrasubstituted imidazoles) and high-purity products were obtained (92-98% for trisubstituted imidazoles and 94-98% for tetrasubstituted imidazoles) in simple multicomponent reactions. The structure of these products was confirmed via FT-IR and NMR. Green and recyclable catalysts, eco-friendly and solvent-free conditions, high catalytic activity, shorter reaction time, easy recovery by an external magnet, high purity, and excellent yields are some features of these reactions.
Facile synthesis of imidazoles by an efficient and eco-friendly heterogeneous catalytic system constructed of Fe3O4 and Cu2O nanoparticles, and guarana as a natural basis
Varzi, Zahra,Esmaeili, Mir Saeed,Taheri-Ledari, Reza,Maleki, Ali
, (2021/01/26)
In this study, an efficient hybrid nanocatalyst made of guar gum (guarana, as a natural basis), magnetic iron oxide nanoparticles, and copper(I) oxide nanoparticles (Cu2O NPs) is fabricated and suitably applied for catalyzing the multicomponent (three- and four-component) synthesis reactions of imidazole derivatives. Here, an easy preparation strategy for this novel catalytic system (Cu2O/Fe3O4@guarana) is presented. Then, the application of this catalytic system for the synthesis of imidazole derivatives is precisely investigated. For this purpose, ultrasonication is introduced as an efficient and fast method. In summary, the high catalytic efficiency of Cu2O/Fe3O4@guarana nanocomposite is well demonstrated by high reaction yields obtained in the presence of a small amount of this nanocomposite, under mild conditions. Wide active surface area, substantial magnetic behavior, excellent heterogeneity, suitable stability, well reusability, and etc. have distinguished this catalytic system as an instrumental tool for facilitating the complex synthetic reactions.
TMSOTf-catalyzed synthesis of trisubstituted imidazoles using hexamethyldisilazane as a nitrogen source under neat and microwave irradiation conditions
Asressu, Kesatebrhan Haile,Chan, Chieh-Kai,Wang, Cheng-Chung
, p. 28061 - 28071 (2021/09/15)
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.
Molecular iodine/DMSO mediated oxidation of internal alkynes and primary alcohols using a one-pot, two step approach towards 2,4,5-trisubstituted imidazoles: Substrate scope and mechanistic studies
Jeena, Vineet,Naidoo, Shivani
supporting information, (2020/02/15)
An efficient, eco-friendly and practical oxidation of internal alkynes and primary alcohols as key steps towards the synthesis of 2,4,5-trisubstituted imidazoles is reported. This green synthetic methodology employed an acid and metal-free molecular iodine/DMSO system, to afford a variety of substituted imidazoles in moderate to good yields, with a range of functionalities tolerated. Mechanistic studies revealed two distinct oxidation pathways, which ultimately form the diketone and aldehyde that serve as key intermediates in the multicomponent domino synthesis.
Catalytic activity of Co(II) Salen&at;KCC-1 on the synthesis of 2,4,5-triphenyl-1H-imidazoles and benzimidazoles
Ali Nasseri, Mohammad,Allahresani, Ali,Naghdi, Elaheh
, (2020/07/31)
The synthesis, reactions and biological properties of imidazoles and benzimidazole make up the bulk of the ring chemistry. In this study, the reaction between different types of aromatic aldehydes and ammonium acetate with diphenylethanedione, in ethanol solvent, using the Co(II) Salen complex&at;KCC-1 catalyst which is produced from Co (II) complex which is supported onto the KCC-1 was studied. The results showed that the products were synthesized in good to excellent yields. The products were identified with IR and NMR spectroscopy. Also, the catalyst was identified by FT-IR, TGA, TEM, and XRD. Finally, the catalyst was reused several times without lack of catalytic activity.
New phosphonium molybdate-promoted green, fast and selective catalytic procedure for the synthesis of trisubstituted imidazoles
Salmasi, Reihaneh,Gholizadeh, Mostafa,Salimi, Alireza
, (2020/05/25)
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.
One-Pot Synthesis of Polysubstituted Imidazoles Based on Pd(OAc) 2 /Ce(SO 4) 2 /Bi(NO 3) 3 Trimetallic Cascade of Decarboxylation/Wacker-Type Oxidation/Debus-Radziszewski Reaction
Li, Peilang,Li, Yiqun,Sun, Wei,Zhang, Mingjuan
supporting information, p. 3221 - 3230 (2019/08/28)
A novel and highly efficient one-pot synthesis of polysubstituted imidazoles from α-hydroxyphenylacetic acids, diphenylacetylene, and amines has been achieved by Pd(OAc) 2 /Ce(SO 4) 2 /Bi(NO 3) 3 trimetallic catalytic system. A series of control experiments showed that this overall reaction occurs through a one-pot cascade process combining the steps of decarboxylation of α-hydroxyphenylacetic acids, Wacker-type oxidation of diphenylacetylene, and Debus-Radziszewski annulation of aryl aldehydes and benzil generated in situ, as well as amines. This reaction represents a novel multicomponent reaction using α-hydroxyphenylacetic acids and diphenylacetylene as sources of aryl aldehydes and a β-diketone. This process exhibits a broad substrate scope and a good functional group tolerance to assemble the corresponding polysubstituted imidazoles in excellent yields (72-88percent) under mild conditions.
Direct synthesis of 2,4,5-trisubstituted imidazoles from primary alcohols by diruthenium(ii) catalysts under aerobic conditions
Sundar, Saranya,Rengan, Ramesh
, p. 1402 - 1409 (2019/02/14)
Herein we report a straightforward synthetic approach to 2,4,5-trisubstituted imidazoles from readily available primary alcohols using arene diruthenium(ii) catalysts. Dinuclear arene ruthenium complexes have been synthesized and structurally characterized with the aid of analytical and spectral techniques. A library of 2,4,5-trisubstituted imidazoles was achieved with a yield up to 95% by loading 0.25 mol% of the catalyst. The present protocol is environmentally benign, which is performed under aerobic conditions and liberates water as the sole by-product.
