An international journal for rapid communication of synthetic organic chemistry, 44. Benzofuran definition and meaning collins english dictionary. Benzofuran derivatives possess several biological properties such as antiinflammatory, antimicrobial, antifungal, antihyperglycemic, analgesic, antiparasitic, and antitumor activities. The derivatives were produced using an intramolecular wittig reaction. In addition substituted benzofurans find application such as of fluorescent sensor 17, oxidant 18, antioxidants, brightening agents, a variety of drugs and in. Benzofuran synthesis through iodocyclization reactions. Some physiological properties of benzofuran and dibenzofuran derivatives earl westley smith iowa state college follow this and additional works at. When this process was carried out in boiling methanol for 16 hours the target benzofuran2carboxylic acid 2hydroxy1,1dimethylethylamides 3a and 3b were obtained in moderate yields. The methodology has been applied for the synthesis of more complex benzofuran derivatives, and may open. Natural source, bioactivity and synthesis of benzofuran. Benzofuran and coumarin derivatives from the root of. The furan derivatives include the benzofused compounds which exist in two forms 1 benzofuran and 2 benzofuran.
The salient features of this method are the easy availability of substrates, high yield, mild reaction conditions, tolerance of a variety of functional groups, and use of an. Bmes 2 afforded the corresponding dimesitylborylation products in good to high yield with excellent regioselectivity. A series of benzofuran derivatives were designed and synthesized, and their inhibitory activites were measured against the sirt. This study reports that a novel phenolic benzofuran derivative could be obtained selectively from g1 by further alkaline treatment. The substrates were obtained by the domino hecksuzuki coupling of 2. The catalytic ch coupling method employs cheap starting materials, exhibits a broad substrate scope, and liberates water as the only byproduct. Abstract benzofurans are among the most popular structural units in bioactive natural products, however, the synthesis of such structures by. Benzofuran as a promising scaffold for the synthesis of. A diversity of synthetic routes can be applied to the synthesis of benzofurans. Recently, benzofuran derivatives have attracted considerable interest for their versatile properties in chemistry and. Benzofurans are chemical compounds which contain a benzofuran ring in their structure.
All structured data from the file and property namespaces is available under the creative commons cc0 license. A thorough study of environmentally friendly hydroxylation of aryl halides is presented. Benzofuran derviatives have shown biological activities ranging from antifungal and antimicrobial to antagonists for the h3 receptor and angiotensin ii. Minor variations of the reaction parameters allow direction of the reactivity furan versus benzene ring and the production of multifunctional 2,3. The successful use of various iodinating agents, bases, additives etc. Dec 10, 20 a palladium0catalyzed cascade reaction for the efficient synthesis of 2,3disubstituted benzofuran derivatives 3 containing a 3trisubstituted alkene functional group in moderate yields from alkynylsubstituted benzynes 1 and aryl halides 2 has been developed. The condensation of 1,4benzoquinone arylsulfonylimines with esters and arylamides of 3alkyl and 3cycloalkylaminocrotonic acids has been studied and the conditions for the cyclization of the resulting products into benzofuran derivatives are discussed. The peptide based benzofuran derivatives have shown potent biological activities. Furtheron,2benzofuran derivatives containingheterocyclic nuclei have shown antibacterial activity towards staphylococcus aureus and candida albicans bacteria 11, and benzoxazole derivatives of benzofurane2carboxamides showed a broad spectrum of antibacterial activity as well.
Benzofuranfused silole and germole derivatives were synthesized by the reactions. Highly fluorescent benzofuran derivatives of the gfp chromophore mikkel andreas christensen, a karsten jennum, a peter b. A green and versatile route to highly functionalized. Wo1999058527a2 benzofuran derivatives, pharmaceutical.
Please, select more pdf files by clicking again on select pdf files. We found that the substituted salicylaldehydes containing different functional groups i. Moreover, 7piperazinylbenzofuran2carbxylic acid amides having halogens or methoxyl groups in benzene ring were patented as partial agonists of 5ht receptors which should. In addition substituted benzofurans find application such. The furan derivatives include the benzofused compounds which exist in two forms 1benzofuran and 2benzofuran. For example, psoralen is a benzofuran derivative that occurs in several plants. In experiments in vitro, all displayed high affinity for a. Onepot synthesis of novel symmetric 1,5dibenzofuran2yl. Synthesis and biological evaluation of new benzofuran. Benzofuran compounds are often analogues of mdxx and tryptamine compounds where a benzofuran ring has replaced the benzodioxole ring structure or indole ring respectively. The main example of the potentiality of this synthetic pathway for the preparation of compounds bearing the benzofuran skeleton is the easily and convenient transformation. Benzofuran is maillard produced present in roasted coffee aroma. It is the parent of many related compounds with more complex structures.
Recent advancements 201417 in the benzofuran synthesis through iodocyclization have been summarized. Bbfg1 dimers, homo and lumo profiles of bbfs1, bbfg1, and bbfg2 pdf. Gouda 2014 reactivity of benzofuran derivatives, synthetic communications. Synthesis of chalcone derivatives of benzo furan as. A palladium0catalyzed cascade reaction for the efficient synthesis of 2,3disubstituted benzofuran derivatives 3 containing a 3trisubstituted alkene functional group in moderate yields from alkynylsubstituted benzynes 1 and aryl halides 2 has been developed. Once files have been uploaded to our system, change the order of your pdf documents. Suggested production of a guaiacyl benzofuran derivative. Electrooxidation enables highly regioselective dearomative. A series of substituted benzofuran derivatives were synthesized and characterized by spectral data. Intramolecular cyclization reactions of green fluorescent protein chromophores gfpc containing an arylethynyl orthosubstituent at the phenol ring provide new arylsubstituted benzofuran derivatives of the gfpc. Once you merge pdfs, you can send them directly to your email or download the file to our computer and view. Some of the synthesized compounds were tested for in vitro. Onepot synthesis of novel symmetric 1,5dibenzofuran2.
Certain benzofuran derivatives are useful in the treatment of certain ischemic or inflammatory conditions, as well as neuroinflammation, neurodegeneration or degenerative diseases in which mitochondrial dysfunction leads to tissue degeneration. Design, synthesis, and biological evaluation of novel benzofuran. Institute of biology and molecular patologies ibpm, department of chemistry, sapienza university of rome, rome, italy. Substituted benzothiophene or benzofuran derivatives as a novel class of bone morphogenetic protein2 upregulators. Synthesis and biological evaluation of new benzofuran carboxamide. Pdf reactivity of benzofuran derivatives researchgate. Natural and synthetic benzofuran derivatives are a class of important organic. Novel benzofuran derivatives bearing naryl piperazine moiety. A series of novel hybrid compounds between benzofuran and naryl piperazine have been. Files are available under licenses specified on their description page. Synthesis and properties of benzofuranfused silole and germole.
Pdf 2acetyl benzofuran 1 was synthesized by refluxing salicylaldehyde and dry chloroacetone in presence of potassium carbonate. Suggested production of a guaiacyl benzofuran derivative from. Journal of chemical and pharmaceutical research, 2017, 95. Benzofuran is a constituent of coix lachrymajobi jobs tears and gentiana lutea yellow gentian benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. The newly synthesized compounds were characterized by ir, nmr and mass spectral data and tested for their pharmacological activities viz. Synthesis, structureactivity relationships and preventive bone loss efficacies in senescence accelerated mice samp6 and ovariectomized rats huifang guo, huayi shao, zhaoyong yang, situ xue, xue li, zongying liu.
Synthesis and evaluation of novel benzofuran derivatives. Synthesis and biological activities of some benzofuran derivatives with 4thiazolidinone moiety a b s t r a c t benzofurans are very interesting heterocycles, which are available in nature and show a wide range of pharmacological activities. The production mechanism and a parallel occurring reaction were also demonstrated. Synthesis of benzofuran derivatives through cascade radical. To change the order of your pdfs, drag and drop the files as you want. This is the first report of the isolation and identification of three furanocoumarin sulfates from a. Most of the benzofurans are research chemicals, most commonly stimulants and entactogens, and are fairly new. Benzofuran derivatives display potent biological properties including antihyperglycemic, analgesic, antiparasitic, antimicrobial, antitumor and kinase inhibitor, activities. A previous literature survey described a variety of 2 substituted benzofuran derivatives that received a great deal of attention for their antihiv18,9,10,11, anticancer11,12,14,15, and antimicrobial11,16,17,18, activities. Natural and synthetic benzofuran derivatives are a class of important organic compounds with a broad range of biological activities, such as antioxidant, antiin. Some physiological properties of benzofuran and dibenzofuran.
Benzofuran coumarone, a heterocyclic compound consisting of fused benzene and furan rings, has been identified as a privileged structure in medicinal chemistry. Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. Benzofuran is the parent of many related compounds with more complex structures. Synthesis of benzofuran derivatives through cascade.
The structures of a total of twelve undescribed compounds were determined by extensive spectroscopic analysis, including 2d nmr data, hydrolysis, and solvolysis, followed by either physicochemical and spectroscopic data or xray crystallographic analysis. Direct dimesitylborylation of benzofuran derivatives by a c. Benzofuran is a fundamental structural unit in a variety of biologically active natural products as well as synthetic materials. Usually these are called as benzofuran and isobenzofuran respectively figure 1. The reaction with diols delivers benzofuran derivatives via dehydrative ch alkenylation and annulation reaction. Benzofuran derivatives are often applied to medical use, antiseptic, pesticide, fuel additive and so on. Merge pdf files combine pdfs in the order you want with the easiest pdf merger available. Pdf synthesis of benzofuran derivatives and their evaluation of. Benzofuran moiety constitutes the core of several interesting pharmacologically active natural products. Benzofuran derivatives from alkynylsubstituted benzynes. Direct dimesitylborylation of benzofuran derivatives by an iridium. Benzofuran derivatives from alkynylsubstituted benzynes and. Synthesis of new benzofuran2carboxylic acid derivatives.
Synthesis and discovery and preliminary sar study of benzofuran derivatives as angiogenesis inhibitors reported by guochun zhuo10. A crystalline antioxidant extracted from yeast was shown to protect in vitro the erythrocytes of vitamin e deficient rats from hemolysis. The benzofuran derivatives are naturally occurring and possess many. The best protocol consists of hydroxylation of different aryl bromides and electrondeficient aryl chlorides by water solution of tetrabutylammonium hydroxide catalyzed by cu2o4,7dihydroxy1,10phenanthroline. Herein, we report a mild and broadly applicable method for the construction of complex benzofurylethylamine derivatives through a unique radical cyclization cascade mechanism. Asteraceae ageratina adenophora, mexico, 2018, antifungal activity, dehydrotrienone benzofuran derivative, ecofriendly. Fluorinated benzofuran derivatives for pet imaging of. It is widely known that benzobfuran derivatives substituted at c2 position show cytostatic andor cytotoxic activity 35.
An efficient synthesis of benzofuran derivatives under. Some of these heteroaromatic compounds exhibit significantly enhanced fluorescence at redshifted emission wavelengths relative to the parent gfpc structure. Derivatives from tyrosol simple and efficient synthesis of. Herein, the series of benzofuran derivatives have been prepared by applying the methods mentioned above. The substituted benzofurans are a class of chemical compounds based on the heterocyclyc and polycyclic compound benzofuran. A simple and convenient approach was developed to the selective synthesis of 3. Benzofurans heterocyclic building blocks sigmaaldrich.
The derivatives of keto benzofuran are useful as medicines, such as amiodarone and benziodarone, particulary for. Mol files containing the results of computations mol. Simple and efficient synthesis of benzofuran derivatives from tyrosol paolo bovicelli1, fabrizio bottaro1, carla sappino1, michela tomei1, valentina nardi1, ilaria proietti silvestri1, beatrice macchi2, caterina frezza2, giuliana righi1 1c. Benzofuran is one of the most important classes of fused ring heterocyclic compounds. Although the relative abundances for the remaining ions are quite similar, the. Benzofuran definition of benzofuran by the free dictionary. The benzofuran derivatives are naturally occurring and possess many biological. Benzofuran derivatives, pharmaceutical composition containing the same, and a process for the preparation of the active ingredient download pdf info. Amide derivatives of halo benzofuran 2carboxylic acid were found to be useful in the treatment of the diseases which are associated with the modulation of h3 receptors. Highly fluorescent benzofuran derivatives of the gfp. In view of the literature survey of benzofuran as a pharmacological agent and on preparation of 1,5dicarbonyl derivatives, here in the present work we report on one pot synthesis of novel symmetric 1,5di benzofuran 2yl34substitutedarylpentane1,5dione derivatives under solvent free condition.
Synthesis and biological activities of some benzofuran. A series of fluorinated benzofuran derivatives as potential tracers for positron emission tomography pet targeting. A phytochemical investigation of the root of angelica dahurica led to the isolation of benzofuran and coumarin derivatives. Abstract direct dimesitylborylation of benzofuran derivatives by a c. Breaking the aromatic systems of electronrich arenes or heteroarenes provides threedimensional chemicals of high added value 1,2,3,4,5,6,7. Hence, different benzofurans having 4thiazolidinones have been synthesized for the purpose. This method provides an efficient and alternative approach to benzofurans which are very useful heterocyclic compounds with. The characterization of 25methoxy1benzofuran3yl n,n.
Benzofuran, solvent free condition, crossed aldol condensation. Similarly some of the benzofuran derivatives have shown very good antimicrobial activity and. The mechanisms of the reactions and their use in the synthesis of biologically active substances are discussed. Direct dimesitylborylation of benzofuran derivatives by an. Furan derivatives methods of synthesis of benzofuran derivatives benzofuran was first synthesized by perkin 3 from coumarin as shown in figure 2. The structure of this compound was determined as benzofuran derivative. It is well known that vitamin e having chroman skeleton have a. The part of the coal oil that contains 2,3benzofuran is made into a plastic called coumaroneindene resin. Reactivity of benzofuran derivatives article pdf available in synthetic communications 4420 october 2014 with 2,217 reads how we measure reads. The obtained ethyl halobenzofuran2carboxylates 2a and 2b were next subjected to the reaction with 2amino2methylpropan1ol in the presence of ammonium chloride. The mechanisms of the reactions and their use in t. Methods for the synthesis of benzofuran derivatives.
99 1096 1514 1221 1185 712 809 1089 1520 69 357 834 655 330 119 437 1519 929 506 1335 841 895 1148 841 1367 468 1599 1644 725 4 1201 912 1007 10 1209 1034 489 1213 1421 911