Benzimidazole derivatives have attracted a significant attention in recent years because of their medicinal applications as antiviral, antiulcer, antifungal, antihypertensive, anticancer, and antihistamine compounds. Respiratory rna viruses are responsible for recurrent acute respiratory illnesses that still represent a major medical need. The standard synthesis for benzimidazoles is the cyclocondensation of ophenylenediamine or substituted ophenylenediamines with carboxylic acids or their derivatives. The synthesis of benzimidazole betaketo sulfides 5af by the reaction of nalkylalphabromo2acetylbenzimidazoles 3ab with 5substituted. Previously we developed a large variety of benzimidazole derivatives able to inhibit these viruses. The cufe 2 o 4 nanoparticles are dioxygen insensitive and easily recoverable with an external. Benzoxazoles and benzimidazoles are important fused nitrogencontaining heterocycles present in a wide range of. Synthesis, characterization, and biological evaluation of. Wed like to understand how you use our websites in order to improve them. Only ortho substituted acid possess both high affinity for the aii receptor and oral antihypertensive potency. Benzimidazole definition of benzimidazole by the free. Synthesis of benzimidazoles the synthesis of benzimidazole. Many of these compounds were found to inhibit the growth of staphylococcus aureus and escherichia coli.
Synthesis of some 6flouro5substituted benzimidazole 12 were reported by alagoz et al. For example, kamble and bhanage reported an improved method to form benzimidazoles from ophenylenediamines and dmf, respectively. This reaction was further explored with the different amides to afford a library of 2substituted benzimidazoles. Imidazole glyoxaline, 1,3diazole a heterocyclic base. The methods for the synthesis of benzimidazoles have become a focus of synthetic. A new route for the synthesis of 2mercapto benzimidazoles. Novel synthesis of benzoxazoles and benzimidazoles. A new series of 2, 5 disubstituted benzimidazole derivatives have been synthesized. New, improved conditions have been developed and optimized for the synthesis of benzimidazoles by intramolecular palladiumcatalyzed arylamination chemistry. The synthesis of eight pyridazino1,6 abenzimidazoles by a novel synthetic route is described. Therefore, more and more inter ests ha ve been ar oused to the synthesis of benzimidazole and its derivatives recently411. An efficient oxidative protocol enables the synthesis of multisubstituted or fused tetracyclic benzimidazoles via a metalfree oxidative cn coupling between the sp 3 ch and free nh of readily available n 1benzylalkyl1,2phenylenediamines in the presence of oxygen and tempo.
Comparative photophysical properties of naphthalene benzimidazoles and naphthalimides are. The structures of the synthesized compounds were confirmed by ir, 1h. Synthesis and photophysical characterizations of thermal. Benzimidazoles article about benzimidazoles by the free.
Synthesis and biological activities of some benzimidazoles. In 1995, bourguignon reported the treatment of ophenylenediamines with dmf for the synthesis of benzimidazoles in the presence of sicl 4 in ch 2 cl 2. Generally, the condensation of ophenylene diamine with carboxylic acids and their nitrile, imidates and orthoester 8 derivatives have been widely used for benzimidazole synthesis. Facile and efficient onepot synthesis of benzimidazoles. Synthesis of benzimidazoles from amino acids with solvent. The synthesis of dicationic extended bisbenzimidazoles. Author links open overlay panel sadaf azeez a popuri sureshbabu a priyanka chaudhary a shahulhameed sabiah b jeyakumar. The present invention provides a direct palladium catalyzed, regioselective process to a wide variety of unsymmetrical, multifunctional nsubstituted benzimidazoles or azabenzimidazoles of. Synthesis and biological activity of novel 2, 5disubstituted. Some of the synthesized compounds showed moderate activity against tested fungi ansari and lal, 2009a, ansari and lal, 2009b. Various catalyzed synthesis of benzimidazole derivatives are known condensation of ophenylenediamine with ortho esters in the presence of.
Anxiety is a psychological and physiological state characterized by cognitive, somatic, emotional, and behavioral components. Several analogues exhibited low micromolar minimal inhibitory concentrations mic against both grampositive and gramnegative bacteria of clinical relevance and could serve as leads for. Almost all syntheses of benzimidazoles start with benzene derivatives possessing nitrogencontaining functions ortho to. Synthesis, characterization, and applications supervising professor. Us3406178a preparation of 2substituted benzimidazoles. The target diamidines show significant in vitro activity against b. Us8188282b2 regioselective palladium catalyzed synthesis. Synthesis and biological activities of some benzimidazoles derivatives. The reaction is catalyzed by pincer complexes of earthabundant cobalt under basefree conditions. The present invention relates to a process for the regioselective synthesis of compounds of the formula i, wherein r0. The synthesis of extended dicationic bisbenzimidazoles starting from trans1,2bis4cyanophenylethene and trans1,2bis4cyanophenylcyclopropane is reported.
The synthesis of benzimidazoles derivative involves subsequent synthesis of 42chloroethoxybenzaldehyde, 4 methyl benzaldehyde. Efficient and inexpensive synthesis of benzimidazoles and quinoxalines. Phenylenediamine via nanoparticles and green strategies using transition metal catalysts sugandha singhal. The reaction mixture was stirred on magnetic stirrer for four hrs. Benzimidazole definition of benzimidazole by medical. Facile and efficient onepot synthesis of benzimidazoles using. 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. It also collects nonringsynthetic approaches to classes of compounds such as nitro, halogeno. Imidazole and benzimidazole synthesis is a comprehensive survey of the known methods of syntheses and ring modification. Microwaveassisted synthesis, photophysical and electrochemical properties of thermalstable naphthalene benzimidazoles and naphthalimides are studied in this paper. A new convenient method for preparation of 2substituted benzimidazoles and bisbenzimidazoles is presented.
A simple and efficient procedure for the synthesis of benzimidazoles using air as the oxidant. Silica sulfuric acid sio 2 oso 3 h as an ecofriendly, readily available, and reusable catalyst is applied to benzimidazole derivatives synthesis under reflux in ethanol. The first chapter provides an introduction to benzimidazoles and nheterocyclic carbenes, a unique class of molecules derived from benzimidazoles. Sulfurdabco promoted reductive couplingannulation cascade reaction between ohydroxyamino nitrobenzenes and benzaldehydes. A heterocyclic compound, c7h6n2, that is used in organic synthesis and inhibits the growth of certain fungi. Synthesis of benzimidazoles the synthesis of benzimidazole derivatives starts from biology 35417 at interamerican san german. 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. The synthesis of benzimidazoles and quinoxalines from. Pdf benzimidazole derivatives are versatile nitrogen containing heterocyclic compounds which have long been known as a.
Here, the synthesis of both classes of compounds starting from aromatic diamines and alcohols benzimidazoles or diols quinoxalines is reported. A set of six novel benzimidazoles compounds were prepared, this includes 5. This new synthetic method is simple, practical and cost saving, and tolerates wide functional groups. Benzimidazoles are a class of heterocyclic, aromatic compounds which share a fundamental structural characteristic of sixmembered benzene. The synthesis of benzimidazole based polyheterocycles draw the. The synthesis and chemistry of certain anthelmintic.
This is a general method of preparing benzimidazoles. Imidazolium chloridecatalyzed synthesis of benzimidazoles. A4, q and j have the meanings indicated in the claims. A green and efficient strategy for the synthesis of benzoxazoles, benzothiazoles and benzimidazoles has been developed by using inexpensive, readily available, dioxygenstable and recyclable cufe 2 o 4 as the nanocatalyst, and osubstituted aminobenzene and various aldehydes as the starting materials. Magnetically recoverable and reusable cufe2o4 nanoparticle. Benzimidazoles heterocyclic building blocks sigmaaldrich. The synthesized benzimidazoles compounds were prepared from the condensation reaction between ophenylenediamine and various carbonyl compounds, in. A series of novel benzimidazole derivatives were synthesized via parallel solutionphase chemistry. Herein, we present the basemetalcatalyzed dehydrogenative coupling of primary alcohols and aromatic diamines to selectively form functionalized 2substituted benzimidazoles, liberating water and hydrogen gas as the sole byproducts. 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. At the same time, many simple benzimidazoles are key intermediates in organic synthesis. 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. Microwaveassisted synthesis of naphthalene benzimidazoles provide higher yields than the conventional thermal synthesis.
In this method, ophenylenediamines were condensed with bisulfite adducts of various aldehydes and dialdehydes under neat conditions by microwave heating. The synthesis and chemistry of certain anthelmintic benzimidazoles lb. Mild and efficient protocol for the synthesis of benzimidazoles using samarium triflate. The research presented in this thesis is centered on the design and synthesis of molecules which are derived from benzimidazoles and their applications. Pharmacological compounds of benzimidazole derivatives are potent inhibitors for a variety of enzymes. Expedient synthesis of benzimidazoles using amides rsc. 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. Since then, a large number of benzimidazoles have been synthesized from 1 and aliphatic acids2023. This relatively unexplored heterocyclic ring system is readily accessible starting from benzoylpropionic acids and phenylhydrazines in five steps. A class of antihelmintic, often used to treat nematodes and cestodes. Iodine is a commercial and environmentally benign catalyst. The synthesized cond exhibited compound exhibited significant of microbiological activity. The most satisfactory method for the synthesis of 2alkylbenzimidazoles 3, r alkyl was developed by phillips2425, which involves refluxing equimolar quantities of the.
Till date numerous reports especially on the synthesis of 2arylbenzimidazoles have been published but lack of knowledge on the detailed synthetic reports of two important derivatives such as. In view of their wide ranging activities, the synthesis of benzimidazoles and its derivatives remain a primary focus for synthetic chemistry communities. The procedure is very simple and the products are isolated with an easy workup in goodtoexcellent yields. Direct synthesis of benzimidazoles by dehydrogenative. As a kind of na tur al biolo gical r esour ce with physiolo gical acti vities, inexpensive amino acids are extensively used in. Recent trends in the synthesis of benzimidazoles from o. In later years, many improvements to the reaction have been made by the use of alternative catalysts. Copperincorporated fluorapatite encapsulated iron oxide.
Pdf an efficient and green synthesis of benzimidazole. A ring system composed of a benzene ring fused with an imidazole ring. An improved procedure for the synthesis of benzimidazoles. This methodology, combined with a catch and release purification strategy, has led to a range of these heterocycles being prepared rapidly and in. This reaction has a wide substrate scope, and the bail gel represents a new catalyst for the synthesis of benzoxazoles, benzimidazoles, and benzothiazoles. The results were also compared with results of synthesis by conventional heating under reflux. Synthetic approaches to benzimidazoles from ophenylenediamine. Herein, two series of thiosemicarbazone and hydrazonebased benzimidazoles have been explored, by derivatizing 5acetyl benzimidazoles previously reported by us.
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