To evaluate the scope of application of this reagent, it was also used to prepare benzothiazole, 1hperimidine, and benzoxazole. The synthesized derivatives were screened for analgesic and antiinflammatory activities. Synthesis and biological activity of novel benzimidazole derivatives as potential antifungal agents. The most commonly used starting material is orthophenylenediamine opda. Imidazole and benzimidazole synthesis is a comprehensive survey of the known methods of syntheses and ring modification. It also collects nonringsynthetic approaches to classes of compounds such as nitro, halogeno. Considerable attention has been focused on the synthesis of benzimidazoles due to having. 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, 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. The chemical structure of the synthesized product was characterized by infra red.
Imidazole and benzimidazole synthesis pdf free download. A novel series of 2substituted benzimidazole derivatives 3a3j were synthesized by the reaction of 2chloro methyl benzimidazole with substituted primary aromatic amines. 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. The resulting solution was cooled and made alkaline to litmus with 10% sodium hydroxide solution. All new synthesized benzimidazole compounds were confirmed by 1h nmr, c nmr spectra, and lc. Several benzimidazole derivatives are reported to exhibit antimicrobial, anticancer,4,5 antifungal,6,7 antiparasitic,8 antiviral,9 antiinflammatory,10 and. Classical methods for benzimidazole synthesis involve the coupling of 1,2diaminobenzene. A welldefined nhcpdiiim complex enables a facile and alternative methodology for the direct ch bond arylation of benzimidazoles with heteroaryl chlorides. The synthesis and chemistry of certain anthelmintic. In the presence of pytz and aerial oxygen, aldehyde reacts with ophenylenediamine or oaminothiophenol under visible light irradiation at ambient temperature to. Synthesis and antifungal activity of 2chloromethyl1h. Antifungal activities of all of the synthesized compounds were evaluated against five phytopathogens fungi cytospora sp. Synthesis, characterization, and biological evaluation of. Synthesis and biological activity of novel benzimidazole derivatives.
Treatment of 26 with potassium thiocyan ate furnishes the key intermediate i acetamido2nitro4. Synthesis of 2substuted benzimidazole from an appropriate ophenylenediamine and orthoester such as. Pdf synthesis and crystal structures of benzimidazole2. A simple and efficient method enables the synthesis of nalkynylheteroarenes from 1,1dibromo1alkenes via a coppercatalyzed crosscoupling reaction. The progress of the reaction was monitored by tlc hexane. Imidazole is an organic compound with the formula c3h4n. Synthesis and biological evaluation of some novel 2phenyl. Synthesis of benzimidazole substituted pyridone azo.
Benzimidazole derivatives parmender singh rathee, ritu dhankar, sunny bhardwaj, monika gupta and rakesh kumar. 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 starting compound 2 bromomethyl 1hbenzimidazole. Generally, the condensation of ophenylene diamine with carboxylic acids and their nitrile, imidates and orthoester 8 derivatives have been widely used for benzimidazole synthesis. Materials and methods chemistry all the chemicals were obtained from sigma aldrich in synthetic grade. Sbsa as a new and efficient catalyst for the onepot green. The 3,6dipyridin2yl1,2,4,5tetrazine pytz derivative shows visible light absorption and reversible oneelectron reduction behavior. Imidazole and benzimidazole synthesis best synthetic. This gene encodes a serinethreonineprotein kinase that play a central role in mitosis. Their structures were characterized by 1h and c nmr and hresims. Synthesis of benzimidazoles the synthesis of benzimidazole. Results and discussion in continuation of our studies on sulfonic acid based catalysts such as silica sulforic acid ssa, silica chloride.
Benzimidazole is produced by condensation of ophenylenediamine with formic acid, or the equivalent trimethyl orthoformate. Phospho sulfonic acid catalyzed synthesis of benzimidazole. In this study, a series of novel quinazolinone derivatives substituted with benzimidazole were synthesized in two parts. 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 baran group synthesis of imidazoles alexandros zografos meeting indroduction. Simple synthesis and biological evaluation of some. The compound, 2mercapto5difluoromethoxy1h benzimidazole, an important intermediate required for the synthesis of pentoprazole, is a new type of medicine intermediate. General procedure for the synthesis of benzoxazoles. Synthesis of benzimidazoles the synthesis of benzimidazole derivatives starts with the benzene derivatives having nitrogen at ortho position to each other. Synthesis of 1 h 1,3benzimidazoles, benzothiazoles and 3. Imidazole and benzimidazole rings are the most important nitrogencontaining heterocycles, which are widely explored and utilized by the pharmaceutical industry for drug discovery.
Synthesis and antifungal activity of benzimidazole. 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. Planar, five membered heteroaromatic molecule with pyrrole type and pyridine type annular nitrogens. Nahso sio promoted synthesis of benzimidazole derivatives. Synthetic routes to benzimidazole based fused polyheterocycles kamal m. Ir kbr, 2800 benzimidazole nh, 1710 and 1670 imide co. These imidazoles share the 1,3c 3 n 2 ring but feature. Development of drugs based on imidazole and benzimidazole.
Jiaswal smriti college of pharmaceutical education. This ring system is present in important biological. All the compounds were characterized by uv, ir, 1 h nmr, mass spectral data and chn elemental analysis. An improved synthesis of 2mercapto5difluoromethoxy. It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution. Synthesis of imidazoles scripps research institute. Treatment of 26 with potassium thiocyan ate furnishes the key intermediate i acetamido2nitro4 thiocyanatobenzene 27. Synthesis and cytotoxic evaluation of novel quinozalinone. Benzimidazole is prepared from ophenylenediamine which is treated with formic acid in presence of alkali. Compound 8 possessed significant potency against mcf. Design and synthesis of substituted imidazole derivatives as antifungal agents 943 design and synthesis of substituted imidazole derivatives as antifungal agents a. Synthesis of nheterocycles benzofused nheterocycles synthesis of benzimidazoles. Generally, condensation of ophenylene diamine with carboxylic acid carboxylic acid and their nitrile, imides and orthoesters 14. 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.
The structures of the synthesized compounds were confirmed by ir, 1h nmr. Synthesis of benzimidazole 2 benzimidazole was prepared according to the reported literature. Synthesis and biological evaluation of 2substituted. Design, synthesis, and characterization of some new benzimidazole. In the past decade, efficient methods have been described for the synthesis of heterocyclic compounds by aryl halides with copper catalysts 17. Several synthetic methodologies are available for the synthesis of benzimidazole. 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, characterization and antimicrobial activity of. Ghafari 1 1 department of medicinal chemistry, faculty of pharmacy and pharmaceutical sciences research center, shiraz university of medical sciences, shiraz, i. The present study describes synthesis of a series of 2. Pantoprazole is a substituted benzimidazole which markedly inhibits basal and stimulated gastric acid secretion. All the synthesized compounds were confirmed by spectral data and then screened for antibacterial activity against b. Simple, mild, and highly efficient synthesis of 2substituted.
Sbsa as a new and efficient catalyst for the onepot green synthesis of benzimidazole derivatives at room temperature 3. A new series of 2, 5 disubstituted benzimidazole derivatives have been synthesized. Publishers london san diego n e w y o r k boston sydney tokyo toronto this book is. The standard synthesis for benzimidazoles is the cyclocondensation of ophenylenediamine or substituted ophenylenediamines with carboxylic acids or their derivatives. Imidazole is an organic compound with the formula c 3 n 2 h 4. The results were also compared with results of synthesis by conventional heating under reflux. Heated together mixture of ophenylenediamine dihydrochloride 0. 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. Synthesis of 2phenyl benzimidazole derivatives prem shankar misra et al. Synthesis and biological activity of novel 2, 5disubstituted.
Alkylated, benzylated and bromoalkylated benzimidazole thione that intramolecularly heterocyclized to 3,4dihydro2h1,3thiazino3,2a benzimidazole were synthesized. It was also used in the preparation of benzimidazolium surfactant, 1hexadecyl1h benzimidazole. Named first as gluoxaline first synthesis with glyoxal and ammonia. Synthesis and antimicrobial studies of novel benzimidazole. Synthesis and antifungal activity of benzimidazole, benzotriazole and aminothiazole derivatives s.
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 benzothiadiazole. Design and synthesis of substituted imidazole derivatives. View enhanced pdf access article on wiley online library html view download pdf for offline viewing. Synthetic routes to benzimidazolebased fused polyheterocycles.
A novel conjugated polymer consists of benzimidazole and. A series of 35 benzimidazole derivatives were synthesized from 2chloromethyl1h benzimidazole in good yields. 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 of 1,1dibromo2,2diphenylcyclopropane 1 in the dry box, sodium tbutoxide 2. This aromatic heterocyclic is a 1, 3diazole and is classified as an alkaloid. Benzimidazole and imidazole derivatives are very useful bioactive. Imidazole and benzimidazole synthesis sciencedirect.
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