Chemistry benzimidazole is a heterocyclic aromatic organic compound. The two carbonnitrogen bonds in benzimidazole when disconnected give ophenylenediamine and formic acid. Synthesis and biological evaluation of benzimidazole. A series of 2substituted benzimidazole having imine linkage were synthesized by two step reactions. Benzimidazole is prepared from ophenylenediamine which is treated with formic acid in presence of alkali. Synthesis of benzimidazole from ophenylenediamine labmonk. These imidazoles share the 1,3c 3 n 2 ring but feature. The first one comprise methyl, the second one comprise of 2 phenyl substitution on benzimidazole moiety. Pdf synthesis of benzimidazole derivatives containing schiff. Benzimidazole derivatives have attracted a significant attention in recent years because of their medicinal applications as antiviral, antiulcer, antifungal, antihypertensive, anticancer, and antihistamine compounds.
Highly efficient and facile method for synthesis of 2. Synthesis and biological evaluation of some novel 2phenyl. Synthesis and biological evaluation of 2substituted benzimidazole. Synthesis of 41hbenzimidazole2ylphenyl3chloro4phenylazetidine2one chloroacetyl chloride 0. The reaction was carried out under very mild conditions at room temperature. Synthesis and antiviral assays of some 2substituted benzimidazolencarbamates, farmaco 55 2000 3539. The structure of the title compounds was elucidated by. A versatile and convenient synthesis of 2substituted benzimidazoles, using o nitroaniline as starting material with several aryl aldehydes, has been accomplished by using a small amount of a reluctant agent. Synthesis and biological evaluation of some novel 2phenyl benzimidazole1acetamide derivatives as potential anthelmintic agents. They are a broad spectrum medication that can act against roundworms and liver flukes. Pdf synthesis of benzimidazole derivatives and study of their. Pharmacological activities benzoxazole is an aromatic organic compound with a molecular formula c7h5no, a benzene fused oxazole ring structure, and an odour similar to pyridine. The synthesis and chemistry of certain anthelmintic. A green and efficient protocol for the synthesis of.
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. Design, synthesis, and characterization of some new benzimidazole. Pharmacological compounds of benzimidazole derivatives are potent inhibitors for a variety of enzymes. Development and synthesis of dnaencoded benzimidazole. Benzimidazole, cancer, metastasis, angiogenesis, sar, protein kinase inhibitors. Substituted benzimidazoles, antimicrobial activity. The versatility of new generation benzimidazole would represent a fruitful pharmacophore for further development of better medicinal agents. Benzimidazole derivatives are versatile nitrogen containing heterocyclic compounds which have long been known as a promising class of biologically active compounds possessing wide variety of biological and pharmacological activities like antibacterial, antiinflammatory, antiulcer, antidiabetic etc. The mixture was stirred for 8 h and allowed to stand at room temperature for 3 days. Onepot synthesis of 2substituted benzimidazole derivatives from ophenylenediamine and a variety of aldehydes were developed under mild reaction conditions. Synthesis of some 6flouro5substituted benzimidazole 12 were reported by alagoz et al.
Onepot synthesis of 7benzimidazol2ylthioxolumazine. Benzimidazole and imidazole derivatives are very useful bioactive intermediates for the preparation of pharmalogical and biological active molecules 16. The recent survey for cancer treatment in cancer facts and figures 2017 american. Imidazole and benzimidazole synthesis is a comprehensive survey of the known methods of syntheses and ring modification. The most prominent benzimidazole compound in nature is nribosyldimethylbenzimidazole, which serves as an axial ligand for cobalt in vitamin b 12. The pmr spectrum of 8 could not be run due to its poor solubility in the common organic solvents. Synthetic approaches to benzimidazoles from ophenylenediamine. Benzimidazole derivatives have occupied a prominent place in medicinal chemistry because of their significant properties as therapeutics in clinical applications. Ir kbr, 30003600 benzimidazole nh, 1720 and 1710 imide co. All synthesis was achieved in hot ethanol by the condensation reaction of an equimolar mixture of substituted amines 2. Abstract a new series of benzimidazole derivatives 1. Coordination behavior of benzimidazole, 2substituted. This reaction led to the formation of benzimidazoles new derivatives in good yields. 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 of benzimidazole betaketo sulfides 5af by the reaction of nalkylalphabromo2acetylbenzimidazoles 3ab with 5substitutedbenzimidazole2thiols 4ac. The most commonly used starting material is orthophenylenediamine opda. We have examined the effect of different solvents using the same reaction conditions. Imidazole is an organic compound with the formula c 3 n 2 h 4. Synthesis of benzimidazoles the synthesis of benzimidazole. Monobmic carboxylic acids used in the synthesis of benzimidazoles. In the first step, ophenylenediamine was condensed with. Compound 8 was also obtained by similar reaction of compounds 4 and 7. All experiments successfully resulted in the desired products.
Imidazole and benzimidazole synthesis sciencedirect. The yield of all benzimidazole derivatives were found to be in the range of 75 94%. A ring system composed of a benzene ring fused with an imidazole ring. Synthesis and antitumour evaluation of novel 2phenylbenzimidazoles. Benzimidazole is produced by condensation of ophenylenediamine with formic acid, or the equivalent trimethyl orthoformate. It is a white or colourless solid that is soluble in water, producing a mildly alkaline solution.
Green chemistry is the new and rapidly emerging field of chemistry. Benzimidazole definition of benzimidazole by medical. There are two general methods for the synthesis of 2substituted benzimidazoles 819. Generally, the condensation of ophenylene diamine with carboxylic acids and their nitrile, imidates and orthoester 8 derivatives have been widely used for benzimidazole synthesis. Eisa et alsynthesis and antimicrobial activity of benzimidazole derivatives 1517 of the cyclized structure was obtained from the absence of ester band in ir, and by 1h nmr, mass spectrometry and elemental analysis scheme ii. Several synthetic methodologies are available for the synthesis of benzimidazole. The yield of all benzimidazole derivatives were found to be in the range of 7594%. Benzimidazoles heterocyclic building blocks sigmaaldrich. Synthesis of benzimidazole several synthetic methodologies are available for the synthesis of benzimidazoles.
Baran, richter essentials of heterocyclic chemistryi heterocyclic chemistry o s n n h n h n h o o n o n s n n h n n h hn n h n n h n n h h o n n h o h s n s s h n n n o o n n h h n n n n ss n n n s n n o n n n h nn s furan pk a. The reaction tolarated many functional groups such as ester, nitro, and chloro. Synthesis of benzimidazoles has been developed by the o phenylenediamine with aldehydes using boric acid an efficient catalyst under mild reaction conditions in aqueous media. The product is applicable to aryl and heteroaryl aldehydes. The benzimidazole nucleus is an important pharmacophore in medicinal chemistry. Simple synthesis and biological evaluation of some. Finally, the key intermediate 16 was alkylated with benzyl chloride in aqueous sodium hydroxide. Generally, condensation of ophenylene diamine with carboxylic acid. Recently the interest in benzimidazole chemistry has been.
Benzoxazole and benzimidazole derivatives were also synthesized by these novel catalysts via the onepot condensation from reaction orthoester with oaminophenol synthesis of benzoxazole derivatives and ophenylenediamine synthesis of benzimidazole derivatives. Synthesize benzimidazole after applying heat to ophenylenediamine and formic acid. The research presented in this thesis is centered on the design and synthesis of molecules which are derived from benzimidazoles and their applications. Experimental procedure a series of nsubstituted benzimidazole derivatives were synthesized to determining their analgesic activity. Synthesis of some benzimidazole derivatives endowed with 1,2,3triazole as potential inhibitors of hepatitis c virus. Synthesis of some benzimidazole derivatives endowed with 1. Synthesis of 2phenyl benzimidazole derivatives prem shankar misra et al. The synthesis and chemistry of certain anthelmintic benzimidazoles lb. Some of the synthesized compounds showed appreciable antifungal activity. Synthetic routes to benzimidazolebased fused polyheterocycles. 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. Therefore, we recommend you professional essay thesis on benzimidazole synthesis pdf tutoring.
We report the synthesis of benzimidazoles using lanthanum chloride as an efficient catalyst. Synthesis and antimicrobial studies of novel benzimidazole. A coppercatalyzed, onepot, threecomponent reaction of 2haloanilines, aldehydes, and nan 3 enabled the synthesis of benzimidazoles in good yields using catalytic amounds of cucl and tmeda in dmso at 120c for 12 h. The present study describes synthesis of a series of 2phenyl benzimidazole1acetamide derivatives and their evaluation for anthelmintic activity using indian adult earthworms, pheretima posthuma. The synthesis of novel benzimidazole derivatives remains a main focus of modern drug discovery. The new nsubstituted benzimidazole derivatives were synthesized from benzimidazole and benzoyl chloride to produce. Synthesis of benzimidazoles the synthesis of benzimidazole derivatives starts with the benzene derivatives having nitrogen at ortho position to each other. Two series of novel benzimidazole derivatives were synthesized.
Synthesis of commercially available benzimidazole involves condensation of ophenylenediamine with formic acid. The purity of the compounds was ascertained by a melting point and tlc. The yields obtained are very good in reasonably short reaction times. An improved and greener protocol for the synthesis of benzimidazole derivatives, starting from. 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. Therefore, synthesis of benziemidazole is affected by simply heating the ophenylenediamine and formic acid together condensation type of reaction. The present study describes a simple, inexpensive, and easy method for synthesis of benzimidazole derivatives in a stipulated time, without using any drastic conditions. Selective and ecofriendly procedures for the synthesis of. Generally, the synthesis of 2substituted benzimidazoles involves the treatment of. The present study describes synthesis of a series of 2. Onepot synthesis of 7benzimidazol2ylthioxolumazine and lumazine derivatives via h 2 so 4catalyzed rearrangement of quinoxalinones when exposed to 5,6diamino2mercapto and 2,5,6triaminopyrimidin4ols.
Similarly, the general synthesis of benzimidazoles is by the condensation reaction of 1,2phenylenediamine with carboxaldehydes, carboxylic acids,6,7 or their. The first chapter provides an introduction to benzimidazoles and nheterocyclic carbenes, a unique class of molecules derived from benzimidazoles. Baran, richter essentials of heterocyclic chemistryi. The synthesis can easily be adapted for the synthesis of the above compounds by exchanging the benzyl cyanide in the first step to pchlorobenzyl cyanide for clonitazene or pethoxybenzyl cyanide for etonitazene. This bicyclic compound consists of the fusion of benzene and imidazole. Synthesis, characterization, and biological evaluation of. This ring system is present in numerous antiparasitic, fungicidal, antithelemintic and antiinflammatory agents 47. In this paper we report the synthesis and in vitro antitumour evaluation of a new series of 2phenyl benzimidazole derivatives bearing oxygenated sub stituents. The most prominent benzimidazole compound in nature is nriosyldimethylbenzimidazole, which serves as a axial ligand for cobalt in vitamin b12. Pdf a new series of non peptide angiotensinaii receptor antagonist has been prepared. Synthesis of 2phenyl benzimidazole derivatives and their schiff bases as possible antimicrobial agents prem shankar misra1, p.
The reaction mixture was stirred on magnetic stirrer for four hrs. The solution is digested for fifteen minutes with about 2 g. 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. Compound 8 synthesis of benzimidazole substituted pyridone azo disperse dyes c2hsoh h2sol d 3 h3c0 qc 0. 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. Seven novel benzimidazole derivatives were synthesized successfully in appreciable yields and characterized physicochemically. Synthesis and analgesic activity evaluation of some new. Synthesis of benzimidazole substituted pyridone azo. Lab chm 20202 maame amoahdankwah synthesis of benzimidazole purpose.
An overview of bulk drug synthesis article pdf available in international journal of pharmtech research 89. Recent progress of benzimidazole hybrids for anticancer. It also collects nonringsynthetic approaches to classes of compounds such as nitro, halogeno. Files are available under licenses specified on their description page. The purity of the compounds were ascertained by a melting point and tlc. A class of antihelmintic, often used to treat nematodes and cestodes. Pdf green chemistry is the new and rapidly emerging field of chemistry.
Benzimidazoles form a family of compounds that act as treatment for nematodes and trematode infections. Facile and efficient onepot synthesis of benzimidazoles. The expert essay tutors at nascent minds will elaborate every single detail to you. Pdf an efficient and green synthesis of benzimidazole. 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.
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