Therefore, synthesis of benziemidazole is affected by simply heating the o phenylenediamine and formic acid together condensation type of reaction. Synthesis of series 1 compounds synthesis of 2methylbenzimidazole. The encoded protein functions in part by phosphorylating members of the mitotic checkpoint complex and activating the spindle checkpoint. Synthetic approaches to benzimidazoles from o phenylenediamine. Benzimidazoles are a class of heterocyclic, aromatic compounds which share a fundamental structural characteristic of sixmembered benzene fused to fivemembered imidazole moiety. This convenient method for the preparation of benzimidazole is related to.
Synthesis of benzimidazole from o phenylenediamine saloni agarwal. Synthesis of benzimidazole from 2nitro4methyl acetanilide synthesis of benzimidazoles virtually starts with benzene derivatives having nitrogencontaining functions ortho to each other like ophenylenediamines 7 opd and reacting with different. Made the cooled reaction mixture distinctly basic by the gradual. Imidazole and benzimidazole synthesis is a comprehensive survey of the known methods of syntheses and ring modification. Nahso 4sio 2, ophenylenediamine, benzimidazole derivatives, aldehydes, reusable catalyst. The most satisfactory method for the synthesis of 2. The synthesis and chemistry of certain anthelmintic benzimidazoles lb.
Chandhrasekar, shameela rajam, christina ruby stella and maruthamuthu. Journal of agricultural and food chemistry 20, 61 11, 27892795. The compound aop was cadenced with aromatic acid chlorides in the presences of pyridine to get compound n21hbenzodimidazol2yl phenyl benzamide ab. The yield of all benzimidazole derivatives were found to be in the range of 75 94%. To prepare benzimidazole from ophenylenediamine reaction. This gene encodes a serinethreonineprotein kinase that play a central role in mitosis. Arbuzov institute of organic and physical chemistry, kazan scientific center of the russian academy of sciences, arbuzov str. The synthesis of hitherto unexplored benzimidazole tethered 1,4oxazepines was accomplished from benzimidazole 2carboxaldehyde in the presence of the incl3catalyzed cyclization reaction. Benzimidazole was used as template compound in the preparation of molecularly imprinted polymer via electropolymerization and electrodeposition of pyrrole on a pencil graphite electrode. We also report the onepot efficient synthesis of other biologically potent compounds, 2mercaptobenzimidazole derivatives under solventfree conditions.
Grassicristaldi and lambarbi have reported the synthesis of benzimidazole by heating ophenylenediamine with chloroform and potassium hydroxide dissolved in ethanol. The tandem synthesis of benzimidazole and other azoles can be achived by the nformylation of orthosubstituted anilines followed by a cyclization reaction. Citations are the number of other articles citing this article, calculated by crossref and updated daily. Herein, we report the efficient onepot solventfree green synthesis of a series of benzimidazole derivatives in good yield at 140oc. Synthesis and pharmacological profile of benzimidazoles. Synthesis of benzimidazole derivative 3a to a mixture of ophenylenediamine 0. Heated together mixture of o phenylenediamine dihydrochloride 0. The intermediate b delivers the desired product c i.
Molecules having benzimidazole motifs showed promising application in biological and clinical studies. Benzimidazole, ophenylenediamine, acetonitrile introduction heterocycles form by far the largest of classical divisions of organic chemistry and are of immense importance biologically and industrially. The reaction of o phenylenediamine with anthranillic acid yield compound 21hbenzodimidazol2yl aniline aop. This research paper deals with the synthesis and diagnose of benzimidazole rings which were have been prepared by using two different methods in which used starting material o phenylenediamine with different compounds. The synthesis and chemistry of certain anthelmintic.
Synthesis of 1 h 1,3benzimidazoles, benzothiazoles and 3. However, co2based nformylations with hydrosilane reducing agents are base catalyzed whereas the cyclization reaction is acid catalyzed. To evaluate the scope of application of this reagent, it was also used to prepare benzothiazole, 1hperimidine, and benzoxazole. Benzimidazole is produced by condensation of ophenylenediamine with formic acid, or the equivalent trimethyl orthoformate. The parent benzimidazole 2 was prepared in 1878 by heating 1 with formic acid19 scheme1. The pmr spectrum of 8 could not be run due to its poor solubility in the common organic solvents.
The mono and disubstituted derivatives of benzimidazole are very interesting heterocyclic organic molecules, synthesized by a simple nucleophilic substitution reaction and condensation method between o. Introduction of a small substituent into the 2 and 5. Synthesis, reactions, and spectroscopic properties of. In the first step, ophenylenediamine will react with benzaldehyde to form the imine intermediate a. Synthesis of benzimidazole 2 benzimidazole was prepared according to the reported literature. The present study describes a simple, inexpensive, and easy method for synthesis of benzimidazole derivatives in a stipulated time, without using any drastic conditions. Pdf synthesis of benzimidazole derivatives containing. A method for the preparation of nr amides of benzimidazole 2carboxylic acid on the basis of the reaction between o phenylenediamine and esters of nr oxamic acids was developed. The resulting solution was cooled and made alkaline to litmus with 10% sodium hydroxide solution. The two carbonnitrogen bonds in benzimidazole when disconnected give ophenylenediamine and formic acid.
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. Behera1 1organic synthesis laboratory, school of chemistry, sambalpur university, jyoti vihar, burla 768019, india, 2maharajahs college of pharmacy, phool baugh, vizianagaram. Benzimidazole structure contains imidazole ring fused with phenyl ring at 4. The synthesis of benzimidazole betaketo sulfides 5af by the reaction of nalkylalphabromo2acetylbenzimidazoles 3ab with 5substituted benzimidazole 2thiols 4ac followed by successive. The reaction mixture was stirred on magnetic stirrer for four hrs. The one pot benzimidazole synthesis described by lee et. Synthesis and characterization of novel benzimidazole embedded 1,3,5trisubstituted pyrazolines as antimicrobial agents gopal k. Cool the clear solution to 15 c, stir magnetically and then add a solution of 7. Compound 8 was also obtained by similar reaction of compounds 4 and 7. To evaluate the scope of application of this reagent, it was also used to prepare benzothiazole, 1hperimidine, and benzoxazole, which was successful. A simple, efficient, and environmentally benign method has been developed for the synthesis of 2substituted benzimidazoles through a onepot reaction of phenylenediamines with aryl aldehydes in ex.
We decided to look at the use of phosphate salt of ophenylenediamine opda for condensing with carboxylic acids for the synthesis of 2. The benzimidazole core was obtained by air oxidative cyclocondensation of o phenylenediamine with benzaldehyde under different conditions. Article views are the countercompliant sum of full text article downloads since november 2008 both pdf and html across all institutions and individuals. 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. A metal free synthesis of benzimidazoles via cyclocondensation of ophenylenediamine with aldehydes is demonstrated the multitasking reagent tertbutyl nitrite has been used as the catalyst all the reactions proceeded at room temperature and gave good to excellent yields of the desired products. The first method is with aldehydes such as 4chlorobenzaldehyde, 4n, ndimethylbenzaldehyde, and formaldehyde. Benzimidazole has been prepared from o phenylenediamine by the action of chloroform and alcoholic potassium hydroxide 1 and of formic acid, 2 and by the reduction of o nitroformanilide. The yield of all benzimidazole derivatives was found to be in the range of 75 94%.
Benzimidazole has been prepared from ophenylenediamine by the action of chloroform and alcoholic potassium hydroxide 1 and of formic acid, 2 and by the reduction of onitroformanilide. Ir kbr, 30003600 benzimidazole nh, 1720 and 1710 imide co. It is a tautomer of a 4h benzimidazole, a 2h benzimidazole and a 3ah benzimidazole. The majority of pharmaceuticals andbiologically active. Imidazole and benzimidazole synthesis sciencedirect. General procedure for the synthesis of benzimidazoles compound b1b5 a mixture of thiocyanate a1a5 0. The resultant benzimidazole was cooled and recrystallised from ethanol. Synthesis and characterization of benzimidazole by using o. In the first step, ophenylenediamine was condensed with pamino benzoic acid in xylene and polyphosphoric acid to give 2amino benzimidazole. A series of benzimidazole derivatives were synthesized by a single step process by reacting o phenylenediamine and benzoic acid.
The purity of the compounds was ascertained by melting point and tlc. Nowadays it is a moiety of choice which possesses many pharmacological properties extensively explored with a. The synthesis of hitherto unexplored benzimidazole tethered 1,4oxazepines was accomplished from benzimidazole 2carboxaldehyde in the presence of the incl 3 catalyzed cyclization reaction. It is a benzimidazole and a polycyclic heteroarene. The invention discloses a synthesis method of a 2substituted benzimidazole compound. Therefore, synthesis of benziemidazole is affected by simply heating the ophenylenediamine and formic acid together condensation type of reaction. Nahso sio promoted synthesis of benzimidazole derivatives. The synthesis results have given a high percentage of the products with different solvent used. The dilemma between acid and base catalysis in the synthesis. Water mediated chemoselective synthesis of 1,2disubstituted benzimidazoles using o phenylenediamine and the extended synthesis of quinoxalines. Heated together mixture of ophenylenediamine dihydrochloride 0.
The two carbonnitrogen bonds in benzimidazole when disconnected give o phenylenediamine and formic acid. Traces of the cyclic benzimidazole 9 can also be detected table 2, entry 3. Synthesis, spectroscopic, xray diffraction and dft studies. Recent trends in the synthesis of benzimidazoles from o. The standard synthesis for benzimidazoles is the cyclocondensation of ophenylenediamine or substituted ophenylenediamines with carboxylic acids or their derivatives. The conventional synthesis generally involved the condensation of these diamines with carbonylcarboxylic acid derivatives either via high temperature heating or via adding strong acids, mostly resulting in poor yields or mixtures. Synthesis, spectroscopic, xray diffraction and dft. Synthesis, characterization and biological evaluation of. Our synthetic work began with an inexpensive precursor, viz. A mild and efficient onepot synthesis enables the preparation of 2substituted benzimidazoles from 1,2phenylenediamines and triacyloxyborane intermediates generated in situ from carboxylic acids and boranethf. Synthesis, reactions and properties of 2substituted benzimidazoles synthesis using cyanogen halides, cyanamide and cyanoguanidines the pierron process is one of the important procedures for the synthesis of several 2amino benzimidazoles 22.
Synthesis of benzimidazole from o phenylenediamine youtube. Generally, the condensation of o phenylene diamine with carboxylic acids and their nitrile, imidates and orthoester 8 derivatives have been widely used for benzimidazole synthesis. Synthesis of benzimidazole from ophenylenediamine l. Synthesis, characterization, and biological evaluation of. Doublecondensation products were selectively obtained when erotf 3 was used as the catalyst in the presence of electronrich aldehydes.
Synthesis and antimicrobial studies of novel benzimidazole. Synthesis of benzimidazole substituted pyridone azo. The reason that my hoffman rearrangement reaction failed was that i dissolved the amide in a naoh solution which hydrolyzed the amide bond. It was also used in the preparation of benzimidazolium surfactant, 1hexadecyl1h benzimidazole. Xxviii was synthesized in 95% yield by reacting ophenylenediamine hydrochloride xxvi with. Journal of chemical and pharmaceutical research, 2012, 411.
Synthesis, characterization and antimicrobial activity of. Synthesis, characterization, and biological evaluation of benzimidazole derivatives as potential anxiolytics dt nannapaneni 1, vsss gupta atyam 2, mi reddy 1, sarva ch raidu 2 1 department of pharmaceutical chemistry, mallareddy college of pharmacy, dhullapally village, hyderabad 500 014, india 2 department of pharmacology, joginpally b. Recent advances in the synthesis of benzimidazolones via. Synthesis, characterization and pharmacological studies of.
A series of 2substituted benzimidazole having imine linkage were synthesized by twostep reactions. As antihypertensive agents article pdf available in ejournal of chemistry 34 january 2006 with 861 reads how we measure reads. 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. Conversely, the formation of monocondensation products was the preferred path in absence of this catalyst.
After confirmation of completion of the reaction, the mixture was chilled in ice and neutralized. Synthesis and antifungal activity of 2chloromethyl1h benzimidazole derivatives against phytopathogenic fungi in vitro. A series of benzimidazole derivatives were synthesized by a single step process by reacting ophenylenediamine and benzoic acid. Synthesis of 1 h 1,3benzimidazoles, benzothiazoles and 3 h. Ammonium chloride is a commercial and environmentally benign catalyst. Synthesis of benzimidazole from ophenylenediamine labmonk. Used in manufacture of dyes, photography, organic synthesis. An improved and greener protocol for the synthesis of benzimidazole derivatives, starting from ophenylenediamine, with different aldehydes is reported. Recent advances in the synthesis of benzimidazolones via rearrangements of quinoxalinon es. In water and in the presence of erotf 3, the diamine and benzaldehyde 1. Jun 28, 2018 an operationally simple method for synthesis of benzimidazole and 3himidazo4,5cpyridine from o phenylenediamine or pyridine3, 4diamine and n,ndimethylformamide dmf in the presence of hexamethyldisilazane hmds as a reagent is described. Further it to then treated with pcl 5 to get an intermediate.
These metrics are regularly updated to reflect usage leading up to the last few days. Also it can be used to synthesize various heterocycles. Synthesis of benzimidazole several synthetic methodologies are available for the synthesis of benzimidazoles. We decided to look at the use of phosphate salt of o phenylenediamine o pda for condensing with carboxylic acids for the synthesis of 2.
The purity of the compounds were ascertained by a melting point and tlc. Journal of chemical and pharmaceutical research, 2012, 4. Besides this, the vital precursors required for knitting the skeleton of benzimidazole are mainly o. In continuation of our earlier studies 1727 on synthesis of benzimidazole derivatives, we wanted to develop an environmentally friendly process for synthesis of 2substituted benzimidazoles. This protocol tolerates acidlabile functional groups. Nahso 4sio 2, o phenylenediamine, benzimidazole derivatives, aldehydes, reusable catalyst. A facile and green synthesis of 2substituted benzimidazoles. Compound 8 synthesis of benzimidazole substituted pyridone azo disperse dyes c2hsoh h2sol d 3 h3c0 qc 0. The reaction of ophenylenediamine with ethoxymethylene. Selective and ecofriendly procedures for the synthesis of. This is a new, convenient and facile methodology for the synthesis of 2substituted1hbenzodimidazoles scheme 16. The drawback in the phillips procedure is that diamine competes for the proton of the acid. Synthesis and characterization of novel benzimidazole.
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