Pdf the synthesis of benzimidazoles derivative involves subsequent synthesis of 42chloroethoxybenzaldehyde, 4 methyl benzaldehyde followed by. Synthesis and characterization of oxadiazole derivatives from benzimidazole 1516 in the present study, a series of novel oxadiazoles were synthesized from benzimidazole and their physical characterization are reported. Synthetic routes to benzimidazolebased fused polyheterocycles. The synthesized benzimidazole compounds were screened for acute and chronic.
Therefore, methods for their preparations are important for synthetic. Synthesis and antifungal activity of benzimidazole. Benzimidazole, green synthesis, biological activity, 2arylbenzimidazole, 2aminobenzimidazole, 2alkylarylthiobenzimidazole. An improved and greener protocol for the synthesis of benzimidazole derivatives. Synthesis of 2phenyl benzimidazole derivatives prem shankar misra et al.
Simon associate professor, department of chemistry, dhanalakshmi srinivasan engineering college, perambalur, tamilnadu ug scholar, department of electronics and communication engineering. Benzimidazole and its derivatives are regarded as an important heterocyclic motif that exhibits a wide range of pharmaceutical applications including anticancers, antihypertensives, antivirals. Coordination behavior of benzimidazole, 2substituted. General procedure for the synthesis of benzimidazole series series a a solution of 590 mg benzimidazole 5 mmol, 0. Functionalization and cyclization reactions of benzimidazoles lead to a wide variety of novel benzimidazole structures. The mixture is stirred vigorously and heated on a steam bath until the solution boils gently. Benzimidazole definition of benzimidazole by medical dictionary. The zinc dust should be at least 80 per cent pure, and the amount used should be equivalent to g. The first one comprise methyl, the second one comprise of 2 phenyl substitution on benzimidazole moiety. Synthesis of benzimidazoles the synthesis of benzimidazole. Imidazole and benzimidazole synthesis is a comprehensive survey of the known methods of syntheses and ring modification. Simple, mild, and highly efficient synthesis of 2substituted.
Synthetic approaches to benzimidazoles from o phenylenediamine. Neutralization of the reaction mixture gave a small amount of from which 6% crude product. As a result of these interests and extensive studies, one health related arena that has benefited. A basis for interest in the benzimidazole ring system as a nucleus from which to develop potential chemotherapeutic agents was established in the 1950s when it was found that 5,6dimethyllalphadribofuranosylbenzimidazole i was an integral part of the structure of vitamin b12. Synthesis of 3,3diphenylcyclopropene 16 list of tables ii. Synthesis and antimicrobial studies of novel benzimidazole. Selective and ecofriendly procedures for the synthesis of. The filtrate is cooled to 1015, and the benzimidazole is filtered and washed with 50 cc. Scheme 9 proposed mechanism of the rearrangement of 2chloroquinoxalines into benzimidazole when exposed to potassium amide in liquid. Satu siri baru terbitan oksadiazol dari benzimidazol telah disintesis dengan mudah oleh. Benzimidazole definition of benzimidazole by medical. Synthesis, characterization, and biological evaluation of. A ring system composed of a benzene ring fused with an imidazole ring. Motivated by the above mentioned facts herein is reported the synthesis and antimicrobial evaluation of new benzimidazole series conjugated with 1,3,4oxadiazole, 1,2,4triazole, 1,3thiazole rings 5a,b.
Synthesis characterization and biological activity benzimidazole derivatives dr. Synthesis and biological evaluation of 2substituted. Benzimidazole is produced by condensation of ophenylenediamine with formic acid, or the equivalent trimethyl orthoformate. General procedure for synthesis of 22phenylhydrazinyl methyl 1h benzimidazole 7. Many benzimidazole derivatives with different pharmacological properties such as anthelmentic11, antiulcer1214. Experimental procedure for the synthesis of benzimidazoles 22. Benzimidazoles heterocyclic building blocks sigmaaldrich. The synthesized compound exhibited by the significant antiinflammatory and antiviral activity. The synthesis and chemistry of certain anthelmintic. Pharmacological compounds of benzimidazole derivatives are potent inhibitors for a variety of enzymes. All the compounds were characterized by uv, ir, 1 h nmr, mass spectral data and chn elemental analysis. The synthesis of benzimidazole betaketo sulfides 5af by the reaction of nalkylalphabromo2acetylbenzimidazoles 3ab with 5substitutedbenzimidazole2thiols 4ac followed by successive. Coordination behavior of benzimidazole, 2substituted benzimidazoles and benzothiazoles, towards transition metal ions. New synthetic procedures, including microwaveassisted synthesis, solid phase synthesis, natural product synthesis, and synthesis of bisbenzimidazoles are briefly described.
The imine can be alkylated and also serves as a ligand in coordination chemistry. Synthesis and antimicrobial activity of certain benzimidazole. Gcms analysis gcms spectra were recorded on an agilient 6890 n gc and 5973 mass selective detector with an hp. It is a benzimidazole and a polycyclic heteroarene. Natural biological substances such as purine bases and vitamin b12 include benzimidazole moiety in their structure.
A highly selective synthesis of benzimidazoles from the reaction of o phenylenediamines. The yield of all benzimidazole derivatives were found to be in the range of 75 94%. To the ethanolic solution of 2chloromethylbenzimidazoles 0. A convenient method for the synthesis of 2substituted benzimidazoles and benzothizoles offers short reaction times, largescale synthesis, easy and quick isolation of the products, excellent chemoselectivity, and excellent yields as main advantages. It is a tautomer of a 4hbenzimidazole, a 2hbenzimidazole and a 3ahbenzimidazole. Substituted benzimidazole derivatives have found commercial application in veterinarian medicine as anthelmintic agents and in diverse human therapeutic pharm chemistry synthesis, characterization, and biological evaluation of benzimidazole derivatives as potential anxiolytics nannapaneni dt, gupta atyam vsss1, reddy mi, sarva raidu ch1. Synthesis of some 6flouro5substituted benzimidazole 12 were reported by alagoz et al. Most significantly, the benzimidazole ring system has been found to be an integral part of vitaminb12 figure1 and figure2 in the form of 5,6dimethyl1 dribofuranosyl benzimidazole. Synthesis of 2phenylbenzimidazole ophenylenediamine 0.
To reveal the mechanism, control experiments were conducted. Two series of novel benzimidazole derivatives were synthesized. It is a chelating agent that forms stable complexes with a number of metals but not calcium. Heterocyclic compounds like benzimidazoles are very important molecules that can be. In the first step, 3chloropropionyl chloride and triethylamine tea were added dropwise to a solution of 2aminothiazole in 1,4dioxane and reacted at reflux temperature. Synthesis of benzimidazole derivatives springerlink.
Thore 301 as a part of our continued work to develop organic reactions in aqueous media,20 we have tried to develop synthesis of 2 aryl benzimidazole in aqueous media, here we report a simple. The structures of the synthesized compounds were characterized using different. Synthesis of benzimidazole and benztoriazole derivatives. Recent advances in the synthesis of benzimidazolones via. The crude product filtrated and extracted by dichloro methane and water. Synthesis of benzimidazole derivative 3a to a mixture of ophenylenediamine 0. A green approach for the synthesis of nalkyl2thiomethyl benzimidazoles 2 rch 3, c 2 h 5, ch 2 ph under different conditions has been developed from nalkyl2chloromethyl benzimidazole i. A concise synthesis of benzimidazoles via the microwaveassisted onepot batch reaction of amino acids up to a 10g scale. Mild and efficient synthesis of 2aryl benzimidazoles in.
New bases and quaternary salts 2methylbenzimidazole derivatives containing 2pyridyl residues as a substituent in various positions of the benzimidazole ring were synthesized. General procedure for the synthesis of 2substituted benzimidazoles and bis. In the scheme 3 the suggested mechanism for the preparation of. Wise a basis for interest in the benzimidazole ring system as a nucleus from which to develop potential chemotherapeutic agents was established in the i95os when it was found that 5,6dimethyl i. Synthesis, antibacterial, antifungal activity and interaction of ct dna with a new benzimidazole derived cu ii complex. The full text of this article hosted at is unavailable due to technical difficulties. 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. The solution is digested for fifteen minutes with about 2 g.
The purity of the compounds were ascertained by a melting point and tlc. Various catalyzed synthesis of benzimidazole derivatives are known condensation of ophenylenediamine with ortho esters in the presence of. Mild and efficient synthesis of 2aryl benzimidazoles in water using sds s. The completion of the reaction was confirmed by tlc ethylacetate. Synthesis, characterization, and microwavepromoted. Pdf synthesis of 1,2disubstituted benzimidazoles using an aza. Benzimidazole derivatives and its biological importance. Synthesis of benzimidazoles the synthesis of benzimidazole derivatives starts from biology 35417 at interamerican san german. Seven novel benzimidazole derivatives were synthesized successfully in appreciable yields and characterized physicochemically. The synthesized derivatives were screened for analgesic and antiinflammatory activities. Benzimidazole, a heterocyclic aromatic organic compound consisting of a fusion of benzene and imidazole, in an extension of the wellelaborated imidazole system, has been used as a carbon skeleton for n heterocyclic carbenes, usually used as ligand for transition metal complexes.
Proposed mechanism for the formation of 1,2disubstituted benzimidazoles b and. There is a growing interest over the past years for the synthesis of benzimidazole based heterocycles due to the crucial role of benzimidazole unit in the functions of biologically important molecules. The synthesis of benzimidazole betaketo sulfides 5af by the reaction of nalkylalphabromo2acetylbenzimidazoles 3ab with 5substituted benzimidazole 2thiols 4ac followed by successive. There is a growing interest over the past years for the synthesis of benzimidazolebased heterocycles due to the crucial role of benzimidazole unit in the functions of biologically important molecules.
The synthesis and chemistry of certain anthelmintic benzimidazoles lb. An efficient approach for the synthesis of 1,2bisubstituted benzimidazoles is presented in this article, and the mechanism of the condensation. Pdf a synthetic approach for 1,2disubstituted benzimidazoles has been successfully designed. A novel series of 2substituted benzimidazole derivatives 3a3j were synthesized by the reaction of 2chloro methyl benzimidazole with substituted primary aromatic amines. Similarly, the general synthesis of benzimidazoles is by the condensation reaction of 1,2. The reaction mixture was stirred on magnetic stirrer for four hrs. Synthesis and medicinal applications of benzimidazoles. Methods for synthesis of benzimidazole derivatives 22komal p et al. A class of antihelmintic, often used to treat nematodes and cestodes. A large excess of zinc dust has been used without changing the yield. From ir spectra, the appearance of peaks at 34003500 cm. 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. The present study describes a simple, inexpensive, and easy method for synthesis of benzimidazole derivatives in a stipulated time, without using any drastic conditions. Some of the issues typically encountered during the synthesis of.
It also collects nonringsynthetic approaches to classes of compounds such as nitro, halogeno. The most prominent benzimidazole complex features nribosyldimethylbenzimidazole as found in vitamin b 12. Several benzimidazole derivatives are reported to exhibit antimicrobial, anticancer, 4,5 antifungal, 6,7 antiparasitic, 8 antiviral, 9 antiinflammatory, 10 and antihistaminic 11 activities. Synthesis, characterization, and microwavepromoted catalytic activity of. Monobmic carboxylic acids used in the synthesis of benzimidazoles. The mechanism of the reaction of organic acids with ophenylenediamines. Generally, the condensation of ophenylene diamine with carboxylic acids and their nitrile, imidates and orthoester 8 derivatives have been widely used for benzimidazole synthesis. A mechanism have been proposed for the preperation of benzimidazoles based. Benzimidazolium salts of a new type with hetaryl groups attached to both nitrogen atoms were obtained. Synthesis and antimicrobial studies of substituted 2. It is a tautomer of a 4h benzimidazole, a 2h benzimidazole and a 3ah benzimidazole. Photoluminescent benzobisimidazolium salts 9 and their physical and photophysical properties.