Boric acid catalyzed convenient synthesis of benzimidazoles. Benzimidazole, green synthesis, biological activity, 2arylbenzimidazole, 2aminobenzimidazole, 2alkylarylthiobenzimidazole. In addition, we introduce the direct synthesis of quinoxalines from nitroarenes and diketones applying our catalyst. Benzimidazole derivatives are among the top frequently used ring systems for small molecule drugs listed by the us fda. Substituted ophenylenediamine for benzimidazoles, 2 mmol. Nickel nitrate promoted synthesis of bioactive 2aryl benzimidazoles and benzothiazoles via schiff base. Pdf synthesis of benzimidazole derivatives and study of their. Benzimidazole is produced by condensation of ophenylenediamine with formic acid, or the equivalent trimethyl orthoformate. Synthesis of benzimidazoles from ophenylenediamines and dmf.
It is a benzimidazole and a polycyclic heteroarene. There are two general methods for the synthesis of 2substituted benzimidazoles 819. Generally, the synthesis of 2substituted benzimidazoles involves the treatment of. The product is applicable to aryl and heteroaryl aldehydes. Benzimidazoles heterocyclic building blocks sigmaaldrich. Synthesis and medicinal applications of benzimidazoles. Generally, benzimidazoles can be synthesized from a variety of starting materials and a few of them are listed below in detail. The direct synthesis of imines, benzimidazoles and. Oxidative cyclization approach to benzimidazole libraries.
Compounds 3a, 3b and 3c were screened for their antibacterial activity against s. An efficient approach to the parallel synthesis of benzimidazoles from anilines is described. The bioinspired orthoquinone catalysts have been applied to heterocycles synthesis. Please cite this article in press as singh mukesh et al. 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. 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. The synthesis and chemistry of certain anthelmintic benzimidazoles lb. Synthesis of benzimidazoles in hightemperature water. The synthesis and chemistry of certain anthelmintic. Generally, the condensation of ophenylene diamine with carboxylic acids and their nitrile, imidates and orthoester 8 derivatives have been widely used for benzimidazole synthesis.
Based on the selectivity pattern observed, the direct iron. Magnetically recoverable and reusable cufe2o4 nanoparticle. Conversely, the formation of monocondensation products was the preferred path in absence of this catalyst. Benzimidazole nucleus plays a very important role as a therapeutic. Benzimidazole definition of benzimidazole by medical dictionary. Pdf an efficient and green synthesis of benzimidazole. Synthesis of benzimidazole from opd by using efficien t green catalyst by ram ineni srinivasulu et al. Synthetic methods photochemistry nitrogen heterocycles a simple and environmentallyfriendly synthetic method for benzimidazoles, which are important structural motifs in.
Benzimidazoles are a class of heterocyclic, aromatic compounds which. Synthesis of novel substituted thiourea and benzimidazole. Onepot synthesis of 2substituted benzimidazole derivatives from ophenylenediamine and a variety of aldehydes were developed under mild reaction conditions. The synthesis of aminobenzimidazoles has been demonstrated under mild reaction conditions using cobalt catalyst in one pot reaction. An efficient solventfree synthesis of imidazolines and benzimidazoles 14 the possible mechanism of this reaction is shown in scheme 2. An efficient approach for the synthesis of benzimidazoles has been developed through the pd. R2 nh 2 nh2 n h n n r1 n h r2 r1 ho o 2position 5position 1. Simple synthesis and biological evaluation of some. Pdf synthesis of 2substituted benzimidazoles and bis. Library approaches to vary the n1 and c2 vectors of benzimidazoles are well established.
The research presented in this thesis is centered on the design and synthesis of molecules which are derived from benzimidazoles and their applications. In the present report an efficient, rapid, facile and inexpensive route for the synthesis of benzimidazoles using 1,2arylenediamines and n,ndimethylformamide in acidic medium under thermalmicrowave condition is developed. We have developed an amidine formationoxidative cyclization sequence that enables. An improved and greener protocol for the synthesis of benzimidazole derivatives, starting from ophenylenediamine, with different aldehydes is reported. A class of antihelmintic, often used to treat nematodes and cestodes. The standard synthesis for benzimidazoles is the cyclocondensation of ophenylenediamine or substituted ophenylenediamines with carboxylic acids or their derivatives. The most satisfactory method for the synthesis of 2alkylbenzimidazoles 3, r alkyl was developed by phillips2425, which involves refluxing equimolar quantities of the diamine and the aliphatic carboxylic acid in 4n. General procedure for the synthesis of 2substituted benzimidazoles and bis benzimidazoles. An efficient solventfree synthesis of imidazolines and. Benzimidazoles from ophenylene diamine with mandelic acid. Doublecondensation products were selectively obtained when erotf 3 was used as the catalyst in the presence of electronrich aldehydes. Mild and efficient synthesis of 2aryl benzimidazoles in. Synthesis and biological evaluation of benzimidazole. Facile and efficient onepot synthesis of benzimidazoles.
A ring system composed of a benzene ring fused with an imidazole ring. The reaction mixture was stirred on magnetic stirrer for four hrs. A green and efficient strategy for the synthesis of benzoxazoles, benzothiazoles and benzimidazoles has been developed by using inexpensive, readily available, dioxygenstable and recyclable cufe2o4 as the nanocatalyst, and osubstituted aminobenzene and various aldehydes as the starting materials. Synthesis of benzimidazole as 1substitutedmethyl2substitutedphenyl benzimidazole 3 was reported by leonardo et al 6. The k4fecn6 increase the electrophilic character at aldehydic carbon, which will facilitate the nucleophilic addition of 1,2. In 1990 various benzimidazole derivatives were synthesized with substitution of fluorine, propylene, tetrahydroquinoline and cyclised compound which resulted. Simple, mild, and highly efficient synthesis of 2substituted. Expedient synthesis of benzimidazoles using amides rsc. The synthesized benzimidazoles compounds were prepared from the condensation reaction between ophenylenediamine and various carbonyl compounds, in. Iodine is a commercial and environmentally benign catalyst.
Benzimidazole synthesis by using boron sulfonic acid as a new. Pharmacological compounds of benzimidazole derivatives are potent inhibitors for a variety of enzymes. 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. Synthesis of benzimidazoles catalyzed by bsa entry diamine 1 aldehyde 2 product 3 yield% a ref. Benzimidazoles and triazoles are useful structures for research and development of new pharmaceutical molecules and have received much attention in the last decade because of their highly potent medicinal activities. Synthetic routes to benzimidazolebased fused polyheterocycles. Synthesis of novel substituted thiourea and benzimidazole derivatives containing a pyrazolone ring as antiin.
We have examined the effect of different solvents using the same reaction conditions. The general method for the synthesis of these benzimidazoles 1 was based on the phillips procedure 27. This methodology involved domino intra and intermolecular c. This is a general method of preparing benzimidazoles.
Synthesis and antimicrobial activity of certain benzimidazole. The solution is digested for fifteen minutes with about 2 g. The synthesized benzimidazoles compounds were prepared from the condensation reaction between ophenylenediamine and various carbonyl compounds. In printed circuit board manufacturing, benzimidazole can be used as an organic solderability preservative. Mechanisms for the synthesis of 1 and 2substitute1,3 benzimidazoles 3 via condensation reaction of phenylenediamines with different aldehydes table 2. This ring system is present in numerous antiparasitic, fungicidal, antithelemintic and antiinflammatory agents 47. Mild and efficient synthesis of 2aryl benzimidazoles in water using sds s.
The present investigation yielded an orange product upon refluxing 2butyramido3chloro1,4naphthoquinone and 2aminopyridine in ethanol. Synthesis, characterization and biological evaluation of 1. Facile and efficient onepot synthesis of benzimidazoles using. The synthesis of benzimidazoles and quinoxalines from. It is a tautomer of a 4h benzimidazole, a 2h benzimidazole and a 3ah benzimidazole.
Synthesis, characterization, and applications supervising professor. New approach is promising and giving moderate yields with high purity and selectively single product in aqueous media 28 scheme 20. Synthesis and pharmacological profile of benzimidazoles. Proposed mechanism for the benzimidazole synthesis under visible light irradiation. The synthesis of benzimidazoles derivative involves subsequent synthesis of 42chloroethoxybenzaldehyde, 4 methyl benzaldehyde followed by benzimidazoles derivative by reaction between amines. The grafting of the bronsted acidic ionic liquid to the surface of teos has increased the catalytic activity of the material and also simplified catalyst recovery from the reaction mixture. Iodine catalyzed synthesis of 2aryl1arylmethyl1hbenzimidazoles is demonstrated by aniket et al. The synthesized cond exhibited compound exhibited significant of microbiological activity. A simple and efficient synthesis of triazole was carried out by treatment of 24azidophenyl1hbenzodimidazole 6 with different types of terminal alkynes in tbuohh2o. As one of the most effective polar solvents for various chemical reactions, n,n dimethylformamide has been employed as a widely utilized reactant in organic transformations such as formylation, amination, and cyanation reactions. When this material was purified, by recrystallization from glacial acetic acid, the melting point was 306 degrees.
The synthesis of benzimidazoles derivative involves subsequent synthesis of 42chloroethoxybenzaldehyde, 4 methyl benzaldehyde followed by benzimidazoles derivative by reaction between amines derivatives and ophenylenediamine in dimethyl farmamide dmf as solvent in the presence of iodine as a catalyst. 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. Nickel nitrate promoted synthesis of bioactive 2aryl. This reaction led to the formation of benzimidazoles new derivatives in good yields. Here, the synthesis of both classes of compounds starting from aromatic diamines and alcohols benzimidazoles or diols quinoxalines is reported.
Elnassan pharmaceutical organic chemistry department, faculty of pharmacy, cairo university, cairo 11562, egypt corresponding author. This work reports the synthesis and characterization of ruthenium nanoparticles ru nps supported on polymeric ionic liquids pils. Jun 22, 2017 synthesis of benzimidazoles from ophenylenediamines and dmf. Oxidative synthesis of benzimidazoles, quinoxalines, and. Without any metal cocatalysts, a sole orthoquinone catalyst enables the oxidative synthesis of benzimidazoles, quinoxalines and benzoxazoles from primary amines in high yields under mild conditions with oxygen as the terminal oxidant. Synthesis and biological activities of some benzimidazoles derivatives. Anxiety is a psychological and physiological state characterized by cognitive, somatic, emotional, and behavioral components. Benzimidazole was synthesized by ophenylene diamine 12 mmol and phenyl glycine 36 mmol were stirred in 4n hcl 40 ml and refluxed for 4 h, then cooled at room. This compound has been shown to be benzodpyridoabenzimidazole 5,12quinone by the present investigation. The synthesis of benzodpyridoabenzimidazole5,12quinone.
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. Experimental section, spectroscopical data and xyz coordinates for all compounds. Benzimidazole and imidazole derivatives are very useful bioactive intermediates for the preparation of pharmalogical and biological active molecules 16. Selective and ecofriendly procedures for the synthesis 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. Liquid phase synthesis of coumarino benzimidazoles for antimicrobial. A set of six novel benzimidazoles compounds were prepared, this includes 5. Since then, a large number of benzimidazoles have been synthesized from 1 and aliphatic acids2023. Synthesis and biological activities of some benzimidazoles. Wed like to understand how you use our websites in order to improve them. Synthesis of 2phenyl benzimidazole derivatives prem shankar misra et al. We report the synthesis of benzimidazoles using lanthanum chloride as an efficient catalyst. Pdf a new series of non peptide angiotensinaii receptor antagonist has been prepared. This catalyst shows high catalytic activity towards the n.
Synthesis of benzimidazoles the synthesis of benzimidazole. Benzimidazoles have also been prepared on a solid phase. Benzimidazole and its derivatives are regarded as an important heterocyclic motif that exhibits a wide range of pharmaceutical applications including anticancers, antihypertensives, antivirals. The most general method is a condensation reaction of o phenylenediamine with carboxylic acids or their derivatives such as nitriles, imidates or ortho esters 10, under strongly acid conditions or in combination with very high temperatures andor. Synthesis of benzimidazoles the synthesis of benzimidazole derivatives starts from biology 35417 at interamerican san german. In continuation, on the synthesis of heterocycles,14 and on the development of synthetic methodologies,1517 we herein report a facile method for the synthesis of benzimidazoles by the condensation of 1, 2phenylenediamine with carbonyl compounds, in the presence of ammonium salts in very good yields. Such reactions provide convenient strategies for synthesis of annulated benzimidazole polyheterocycles. Experimental procedure for the synthesis of benzimidazoles 22.
In addition, functional group tolerance has been also explored. Synthesis and evaluation of selected benzimidazole. Benzimidazole derivatives have attracted a significant attention in recent years because of their medicinal applications as antiviral, antiulcer, antifungal, antihypertensive, anticancer, and antihistamine compounds. The reaction parameters, such as temperature, density and reaction time, have been systematically studied to understand whether the solvent properties of hightemperature water can have a positive effect on the chemistry. Synthesis of 2substituted benzimidazoles and bis benzimidazoles by microwave in the presence of aluminamethanesulfonic acid.
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