5-(4-Chlorophenyl)-N,1-di-o-tolyl-1H-imidazole-2-amine (original) (raw)
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Zeitschrift für Naturforschung B, 2015
Ten 1,2,4,5-tetra-substituted imidazole derivatives have been synthesized with a 2-hydroxyethy substituent at the 1-nitrogen atom and potentially electron releasing hydroxy-, methoxy-, dimethylamino- or nitro substituents in various positions on the benzene ring located on the 2-carbon atom. The prototypical derivative with an unsubstituted phenyl ring at the 2-position is also reported. The compounds are obtained in excellent yields (average 86%) via a four-component cyclocondensation reaction of benzil, ethanolamine, and the appropriate aromatic carbaldehyde together with ammonium acetate. The reaction uses a novel ionic liquid catalyst, DEAHS (diethyl ammonium hydrogen sulfate), under solvent-free conditions and a green synthetic protocol. The key advantages of this process are high yield, shorter reaction times and ease of work-up. Furthermore, the products can be purified by a non-chromatographic method and the catalyst is re-usable. All of these newly synthesized compounds hav...
Synthesis of the Guanidine Derivative: N-{(7-(4,5-Dihydro-1H-imidazol-2-yl)-2-(p-tolyl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene)aminomethylene}benzamide
2021
The guanidine derivative N-{[(7-(4,5-dihydro-1H-imidazol-2-yl)-2-(p-tolyl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene)amino](phenylamino)methylene}benzamide (3) has been obtained by the reaction of one measure of N-{[7-(4,5-dihydro-1H-imidazol-2-yl)-2-(p-tolyl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene]carbamothioyl}benzamide (2) with one measure of aniline in the presence of mercury(II) chloride and triethylamine in anhydrous dimethylformamide. The structure of product 3 was confirmed by 1H and 13C-NMR, infrared spectroscopy, and elemental analysis.
Scientia Iranica, 2013
A mild, efficient and environmentally friendly method has been developed for the green synthesis of 2,4,5-trisubstituted imidazoles via a three-component one-pot condensation of 1,2-diketones, diammonium hydrogen phosphate, (NH4)2HPO4(DAHP) and aryl aldehydes in waterunder reflux conditions. The DAHP shows remarkable activities for the synthesis of title compounds.The key advantages of this method toward conventional methods are experimental simplicity, good functional group tolerance; excellent yields, short routine, and selectivity without the need for a transition metal or base catalyst.
Synthesis of Triphenyl Imidazole by Green chemistry approach
World Journal of Biology Pharmacy and Health Sciences, 2024
Synthesis of 2,3,5-Triphenyl imidazole is carried out by conventional method/ traditional method as well as green chemistry in the present study. Green chemistry is also known as microwave assisted synthesis. Green chemistry is the design of chemical products and process that eliminates the use and generation of hazardous substances. Using green solvent, like water, synthesis of biologically active moiety with high percentage yield as well as purity. The Percentage yield of 2,3,5-Triphenyl imidazole obtained by Green Chemistry Approach is 90.90% whereas Conventional/Traditional method produces only 69.60% of 2,3,5-Triphenyl imidazole constant concentration of all organic reagents. Hence, we concluded that green chemistry approach is environment friendly.
Journal of the Iranian Chemical Society, 2014
To date, the synthesis of various derivatives of these compounds has been reported [13-18]. The most common synthetic methods reported for the preparation of imidazo[1,2-a]pyrimidine ring systems involve closure of the imidazole ring by the condensation of 2-aminopyrimidine and closure of the pyrimidine ring by the condensation of 2-aminoimidazole with appropriate electrophilic compounds. Synthesis of imidazo[1,2-a]pyrimidines via condensation of 2-aminopyrimidine with α-halocarbonyl compounds has also been developed. The drawback of this method is difficulty in preparation, purification, toxicity, and lachrymatory property of α-halocarbonyl compounds which limit its reliability. Taking this fact into account, developing an efficient and simple route for synthesis of imidazo[1,2-a] pyrimidines is of great interest [19-24]. In our efforts to use MCRs in the synthesis of heterocycles [25-27], herein we present a multi-component and efficient route for the synthesis of novel imidazo[1,2-a] pyrimidines from the reaction of aldehydes, 2-amino-benzimidazole, and α-tetralone in the presence of catalytic amount of p-toluene sulfonic acid (Scheme 1). Experimental procedures A mixture of aldehydes (10 mmol), 2-amino-benzimidazole (10 mmol), and α-tetralone (10 mmol) with catalytic amount of p-toluene sulfonic acid (0.5 mol%) was refluxed in EtOH in appropriate reaction time. The progress of the reaction was monitored by TLC. At the end of reaction, the precipitated products were filtered and recrystallized from n-hexane: chloroform mixture (1.5:2). Characterization was performed using 1 H and 13 C NMR, FTRI, and GC techniques.
Tetrahedron Letters, 2009
Heating a neat 1:2 mixture of 2-picolylamine and 2-cyanopyridine followed by treatment of the resultant red gummy substance with aqueous KOH resulted in the isolation of 2,4,5-tris(2-pyridyl)imidazole (1a) as the major product and N-(3-(2-pyridyl)imidazo[1,5-a]pyridine)picolinamidine (2a) in small amounts. Similarly, by using 3-picolylamine, 2,4,-bis(2-pyridyl)-5-(3-pyridyl)imidazole (1b) and N-(3-(3-pyridyl)imidazo[1,5-a]pyridine)picolinamidine (2b) were isolated, and by using 4-picolylamine, 2,4,-bis(2pyridyl)-5-(4-pyridyl)imidazole (1c) and N-(3-(4-pyridyl)imidazo[1,5-a]pyridine)picolinamidine (2c) were isolated. The plausible mechanism of the formation of 1a-c and 2a-c is delineated. The imidazole ring system is an important function in biology, chemistry as well as in pharmaceutical, veterinary, and agrochemical products. 1-4 They are useful ligands in coordination chemistry and the synthesis of the compounds containing the imidazole ring is an important area of scientific investigation. 1-3 Multicomponent reaction (MCR) methods involving the isocyanides as one of the components for the synthesis of imidazole derivatives have been reviewed. 5 The synthesis of the 1,2,4-trisubstituted imidazole by palladium-catalyzed cyclization of O-pentafluorobenzoylamidoximes is reported. 6 Addition reaction of imidazolium ylides to electron-deficient imines is a useful method for the synthesis of 2-(a-substituted-amidoalkyl)imidazoles. 7 An efficient, mild one-pot method for preparing polysubstituted imidazoles from aryl-substituted tosylmethyl isocyanide (TosMIC) reagents and in situ generated imines 8 as well as a new synthetic approach for the synthesis of chiral imidazoles using thio-Ugi reaction 9 have been reported. The synthesis of the annulated terpene-imidazole, 10 a microwave assisted organic synthesis (MAOS) method for the synthesis of 2,4,5-triaryl-imidazole 11a as well as the synthesis, and p38 MAP kinase inhibitor property 11b have been described.
A mild, eecient and environmentally friendly method has been developed for the green synthesis of 2,4,5-trisubstituted imidazoles via a three-component one-pot condensation of 1,2-diketones, diammonium hydrogen phosphate, (NH4)2HPO4 (DAHP) and aryl aldehydes in water under reeux conditions. The DAHP shows remarkable activities for the synthesis of title compounds. The key advantages of this method over conventional methods are experimental simplicity, good functional group tolerance, excellent yields, short routine, and selectivity, without the need for a transition metal or base catalyst.
PROSPECTS FOR THE CHEMISTRY OF IMIDAZOLE DERIVATIVES (Review)
Chemical Journal of Kazakhstan
The problem of creating new effective domestic pharmacological preparations, including the development of the methods for obtaining biologically active substances in compliance with the “green chemistry” principles, are among the priority areas for the development of chemical science. The choice of an initial molecule, which carries the potential of biological activity, is the guarantor of a successful experimental search. Imidazole derivatives occupy a unique place in the medicinal chemistry. An imidazole cycle is part of the natural compounds such as histamine, biotin, some alkaloids and nucleic acids, and is a structural fragment of medicinal preparations. The goalof the present review is to analyze the publications on the chemistry of imidazole derivatives with an emphasis on the methods of obtaining biologically active and other practically useful molecules with an obligatory imidazole cycle. The objects of the study:imidazole derivatives. The examples of the routes of synthesi...
Synthetic Communications, 2017
An Efficient, convenient green approach for the synthesis of Indole-based2,4,5trisubstituted and 1,2,4,5-tetra substituted imidazoles by multicomponent reaction of substituted 2-arylindole-3-carbaldehydes, benzil, substituted anilines and ammonium acetate using catalytic aminoacid (Glycine) in ethanol is described. Several amino acids have also been evaluated as organic catalysts for these reactions. The structures of the compounds have been established on the basis of infrared, mass and 1H NMR spectral data. The mild reaction conditions, inexpensive / economical reagents and good yield show the usefulness of this approach.
One pot three-component synthesis of imidazole derivatives using NH3/NH4Cl
2017
Imidazole is a planar, five membered heteroaromatic molecule with pyrrole type and pyridine type annular nitrogens. Several approaches are available of imidazoles from alpha halo ketones, aminonitrile, aldehyde ect. Reactivity of imidazole and benzimidazole is referred from sets of resonance structure in which the dipolar contributors have finite importance. Imidazoles among the principal groups of heterocyclic compounds that have biological properties. Due to the presence of imidazole rings in natural products and active pharmaceutical ingredients, different ways for the synthesis of heterocyclic compounds of this type investigated. The aim of this project is substituted derivatives 2,4,5-Imidazoles. In this study, three-substituted imidazole compounds synthesized using ammonium chloride as a catalyst cost in terms of reflux were studied. Reaction with aldehydes and ammonium acetate Acenaphthene quinone in crowding conditions in the presence of ammonium chloride was performed suc...