The equimolar amount of amines derivatives and ophenylenediamine were diluted in equimolar amount of dimethyl formamide dmf as solvent to a different round bottom flask and both are mixed and stirred for 30 min. Imidazole 1 refers to the parent compound,whereas imidazoles are a class of heterocyclic with similar ring structure, but varying substituents. Design and synthesis of substituted imidazole derivatives. Generally, condensation of ophenylene diamine with carboxylic acid carboxylic acid and their nitrile, imides and orthoesters 14. Imidazole and benzimidazole synthesis best synthetic. The standard synthesis for benzimidazoles is the cyclocondensation of ophenylenediamine or substituted ophenylenediamines with carboxylic acids or their derivatives. Design and synthesis of substituted imidazole derivatives as antifungal agents 943 design and synthesis of substituted imidazole derivatives as antifungal agents a. Imidazole is an organic compound with the formula c3h4n.
Imidazole is an organic compound with the formula c 3 n 2 h 4. Results and discussion in continuation of our studies on sulfonic acid based catalysts such as silica sulforic acid ssa, silica chloride. The progress of the reaction was monitored by tlc hexane. An improved synthesis of 2mercapto5difluoromethoxy. All new synthesized benzimidazole compounds were confirmed by 1h nmr, c nmr spectra, and lc. Simple, mild, and highly efficient synthesis of 2substituted. Synthesis, characterization, and biological evaluation of.
Heated together mixture of ophenylenediamine dihydrochloride 0. Antifungal activities of all of the synthesized compounds were evaluated against five phytopathogens fungi cytospora sp. Synthesis and biological evaluation of some novel 2phenyl. Nahso sio promoted synthesis of benzimidazole derivatives. Imidazole and benzimidazole synthesis is a comprehensive survey of the known methods of syntheses and ring modification. Green synthesis of benzimidazole derivatives p a g e 624 benzimidazole derivatives in current years, various reports which were related to synthesis of nitrogen n, oxygen o and sulphur s containing heterocyclic had appeared owing to an extensive variety of their pharmacological activities. A simple and efficient method enables the synthesis of nalkynylheteroarenes from 1,1dibromo1alkenes via a coppercatalyzed crosscoupling reaction. Planar, five membered heteroaromatic molecule with pyrrole type and pyridine type annular nitrogens. The synthesis and chemistry of certain anthelmintic. Phospho sulfonic acid catalyzed synthesis of benzimidazole.
In the past decade, efficient methods have been described for the synthesis of heterocyclic compounds by aryl halides with copper catalysts 17. Synthesis of nheterocycles benzofused nheterocycles synthesis of benzimidazoles. The 3,6dipyridin2yl1,2,4,5tetrazine pytz derivative shows visible light absorption and reversible oneelectron reduction behavior. Jiaswal smriti college of pharmaceutical education. Classical methods for benzimidazole synthesis involve the coupling of 1,2diaminobenzene. Alkylated, benzylated and bromoalkylated benzimidazole thione that intramolecularly heterocyclized to 3,4dihydro2h1,3thiazino3,2a benzimidazole were synthesized. Imidazole and benzimidazole synthesis pdf free download. It also collects nonringsynthetic approaches to classes of compounds such as nitro, halogeno. In this method, ophenylenediamines were condensed with bisulfite adducts of various aldehydes and dialdehydes under neat conditions by microwave heating. Synthesis of benzimidazole 2 benzimidazole was prepared according to the reported literature.
Benzimidazole was used as template compound in the preparation of molecularly imprinted polymer via electropolymerization and electrodeposition of pyrrole on a pencil graphite electrode. Synthesis and biological activity of novel 2, 5disubstituted. General procedure for the synthesis of benzoxazoles. An operationally simple method for synthesis of benzimidazole and 3himidazo4,5cpyridine from ophenylenediamine or pyridine3, 4diamine and n,ndimethylformamide dmf in the presence of hexamethyldisilazane hmds as a reagent is described. The results were also compared with results of synthesis by conventional heating under reflux. Design, synthesis, and characterization of some new benzimidazole. Benzimidazole is produced by condensation of ophenylenediamine with formic acid, or the equivalent trimethyl orthoformate. The starting compound 2 bromomethyl 1hbenzimidazole. This gene encodes a serinethreonineprotein kinase that play a central role in mitosis. Synthesis of 2substuted benzimidazole from an appropriate ophenylenediamine and orthoester such as. Generally, the condensation of ophenylene diamine with carboxylic acids and their nitrile, imidates and orthoester 8 derivatives have been widely used for benzimidazole synthesis. Imidazole and benzimidazole rings are the most important nitrogencontaining heterocycles, which are widely explored and utilized by the pharmaceutical industry for drug discovery.
It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. Compound 8 possessed significant potency against mcf. Synthesis of benzimidazole substituted pyridone azo. Synthesis and antifungal activity of benzimidazole. Considerable attention has been focused on the synthesis of benzimidazoles due to having. Synthesis and antimicrobial studies of novel benzimidazole. Treatment of 26 with potassium thiocyan ate furnishes the key intermediate i acetamido2nitro4. The paper describes the synthesis and biological evaluation of some new benzimidazole derivatives as potent clinical drugs that are useful in the treatment of some microbial infections and tumor inhibition.
A new convenient method for preparation of 2substituted benzimidazoles and bisbenzimidazoles is presented. Ravi kumar and peruri veera venkata satyanarayana and bonam srinivasa reddy, year2012 a library of benzimidazole derivatives have been prepared through the reaction of. The chemical structure of the synthesized product was characterized by infra red. Due to their special structural features and electronrich environment, imidazole and benzimidazole containing drugs bind to a variety of therapeutic targets, thereby exhibiting a broad spectrum of. Similarly, the general synthesis of benzimidazoles is by the condensation reaction of 1,2phenylenediamine with carboxaldehydes, carboxylic acids,6,7 or their derivatives8,9 such as, chlorides, nitriles, and orthoesters, under strong acidic conditions, with high temperatures. Synthesis of benzimidazoles the synthesis of benzimidazole. All the compounds were characterized by uv, ir, 1 h nmr, mass spectral data and chn elemental analysis. A new series of 2, 5 disubstituted benzimidazole derivatives have been synthesized. The synthesized derivatives were screened for analgesic and antiinflammatory activities. Named first as gluoxaline first synthesis with glyoxal and ammonia. The most commonly used starting material is orthophenylenediamine opda. It brings together the multitude of synthesis of the imidazole ring in a systemic way interms of specific bond formation, and recommends the most attractive synthetic. It was also used in the preparation of benzimidazolium surfactant, 1hexadecyl1h benzimidazole. Simple synthesis and biological evaluation of some.
Synthesis of 2phenyl benzimidazole derivatives prem shankar misra et al. A series of 35 benzimidazole derivatives were synthesized from 2chloromethyl1h benzimidazole in good yields. To evaluate the scope of application of this reagent, it was also used to prepare benzothiazole, 1hperimidine, and benzoxazole. This ring system is present in important biological. Synthesis and antifungal activity of benzimidazole, benzotriazole and aminothiazole derivatives s. Synthesis and antifungal activity of 2chloromethyl1h. Pdf synthesis and crystal structures of benzimidazole2. Ghafari 1 1 department of medicinal chemistry, faculty of pharmacy and pharmaceutical sciences research center, shiraz university of medical sciences, shiraz, i. A novel conjugated polymer consists of benzimidazole and benzothiadiazole. Publishers london san diego n e w y o r k boston sydney tokyo toronto this book is. Synthesis and biological activity of novel benzimidazole derivatives.
Imidazole and benzimidazole synthesis sciencedirect. Benzimidazole is prepared from ophenylenediamine which is treated with formic acid in presence of alkali. Benzimidazole derivatives parmender singh rathee, ritu dhankar, sunny bhardwaj, monika gupta and rakesh kumar. In this five step synthesis, 4chloro2nitroaniline 25 is first acetylated with acetic anhydride to give i acetamido4chloro2nitro benzene 26. Treatment of 26 with potassium thiocyan ate furnishes the key intermediate i acetamido2nitro4 thiocyanatobenzene 27.
This aromatic heterocyclic is a 1, 3diazole and is classified as an alkaloid. Synthesis of benzimidazoles the synthesis of benzimidazole derivatives starts with the benzene derivatives having nitrogen at ortho position to each other. Good yields and functionalgroup tolerance were obtained with tmeda as ligand using imidazole and benzimidazole substrates in dioxane. A novel conjugated polymer consists of benzimidazole and. Synthetic routes to benzimidazole based fused polyheterocycles kamal m. The resulting solution was cooled and made alkaline to litmus with 10% sodium hydroxide solution.
Synthesis, characterization and antimicrobial activity of. Synthetic routes to benzimidazolebased fused polyheterocycles. View enhanced pdf access article on wiley online library html view download pdf for offline viewing. A novel series of 2substituted benzimidazole derivatives 3a3j were synthesized by the reaction of 2chloro methyl benzimidazole with substituted primary aromatic amines. The baran group synthesis of imidazoles alexandros zografos meeting indroduction.
Synthesis and cytotoxic evaluation of novel quinozalinone. Benzimidazole and imidazole derivatives are very useful bioactive. There is a growing interest over the past years for the synthesis of benzimidazole based. Sbsa as a new and efficient catalyst for the onepot green synthesis of benzimidazole derivatives at room temperature 3. Materials and methods chemistry all the chemicals were obtained from sigma aldrich in synthetic grade.
It brings together the multitude of synthesis of the imidazole ring in a systemic way interms of specific bond formation, and recommends the most attractive synthetic approaches. Synthesis, 1997 imidazole and benzimidazole synthesis m. In chemistry, it is an aromatic heterocycle, classified as a diazole, and has nonadjacent nitrogen atoms many natural products, especially alkaloids, contain the imidazole ring. Pantoprazole is a substituted benzimidazole which markedly inhibits basal and stimulated gastric acid secretion. Methods of benzimidazole synthesis include the condensation of oaryldiamines and aldehyde in refluxing nitrobenzene 2,3, the condensation of oaryldiamines with carboxylic acids or their derivatives in the presence of strong acids such as polyphosphoric acid 4 or mineral acids 5 and the thermal or acid promoted cyclization of n. Synthesis of 1,1dibromo2,2diphenylcyclopropane 1 in the dry box, sodium tbutoxide 2. In this study, a series of novel quinazolinone derivatives substituted with benzimidazole were synthesized in two parts. Development of drugs based on imidazole and benzimidazole. These imidazoles share the 1,3c 3 n 2 ring but feature. Synthesis and biological activity of novel benzimidazole derivatives as potential antifungal agents. Synthesis of 1 h 1,3benzimidazoles, benzothiazoles and 3. All the synthesized compounds were confirmed by spectral data and then screened for antibacterial activity against b. The compound, 2mercapto5difluoromethoxy1h benzimidazole, an important intermediate required for the synthesis of pentoprazole, is a new type of medicine intermediate. Sbsa as a new and efficient catalyst for the onepot green.
A welldefined nhcpdiiim complex enables a facile and alternative methodology for the direct ch bond arylation of benzimidazoles with heteroaryl chlorides. The structures of the synthesized compounds were confirmed by ir, 1h nmr. In the presence of pytz and aerial oxygen, aldehyde reacts with ophenylenediamine or oaminothiophenol under visible light irradiation at ambient temperature to. Several synthetic methodologies are available for the synthesis of benzimidazole. Ir kbr, 2800 benzimidazole nh, 1710 and 1670 imide co. Their structures were characterized by 1h and c nmr and hresims.
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