The substrates were obtained by the domino hecksuzuki coupling of 2. These compounds showed optical and electrochemical properties that differ from their benzothiophene analog. Synthesis of benzofuran derivatives and their evaluation 639 results and discussion the scheme of synthesis of titled compounds is depicted in the scheme 1. Synthesis of chalcone derivatives of benzo furan as. Benzofuran is a fundamental structural unit in a variety of biologically active natural products as well as synthetic materials. In the literature, there are few studies on the synthesis of khellinone derivative chalcone compounds. A thorough study of environmentally friendly hydroxylation of aryl halides is presented. Further it was planned to modify the carboxylic acid functionality by electron donor. The anticancer activities of novel synthesized derivatives were evaluated against. Results and discussion the first set of experiments was directed towards the onepot protectioncouplingcyclization of bromohydroquinone 6, figure 3. The structure of this compound was determined as benzofuran derivative. Synthesis of benzofuran derivatives on solid support via smi2. Realizing the importance of benzofuran derivatives in the synthesis of various drug sources reported in few classical methods such as, cyclocondensation of salicylaldehyde with. Benzofuran is maillard produced present in roasted coffee aroma.
Dec 27, 20 the synthesis of novel series of benzofuran derivatives, containing barbitone moiety, 524substitutedphenyl5substituted1benzofuran2yl methylidenepyrimidin2,4,61h,3h,5htrione 4ai and thiobarbitone moiety, 524substitutedphenyl5substituted1benzofuran2ylmethylidene2thioxodihydropyrimidin4,61h, 5hdione 5ai have been reported. Exploitation of donoracceptor cyclopropanes and nsulfonyl 1. Syntheses of benzofuran 2carboxylic acid derivatives are important in the development of many biologically active molecules for potential use in the treatment of cancer as well as central nervous system disorders. Synthesis and biological activities of some benzofuran. The possible mechanism of the novel rearrangement was also discussed. Synthesis and biological evaluation of new benzofuran. Synthesis of benzofuran derivatives and their evaluation of. The present work describes the synthesis and characterization of six new dyes. Comparative studies of synthesis of symmetric 2,6di. Benzofuran derivatives from alkynylsubstituted benzynes. Synthesis of benzofuran derivatives via rearrangement and.
C bonds has been achieved with a variety of substitution patterns. Synthesis and antimicrobial evaluation of new benzofuran. The mechanisms of the reactions and their use in t. Synthesis of benzofuran derivatives on solid support via. Physical properties of 3 benzofuran 2yl1phenyl pyrazoline derivatives 610. General procedure for synthesis of benzofuran 2carboxylic acid 2hydroxy1,1dimethylethylamides 3a, 3b a mixture of benzofuran 2carboxylic acid ethyl esters 2a or 2b 0. For example, psoralen is a benzofuran derivative that occurs in several plants. Synthesis of potent antitumor and antiviral benzofuran derivatives. Synthesis of benzofuran derivatives through cascade radical. 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 literature shows that compounds with benzofuran nucleus have a wide.
Aryl benzofuran derivatives and oligostilbene derivatives. The methodology allows the facile production of heterobiaryl compounds, a unique. Application of radical chemistry to solid support synthesis. Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4 methy1enedioxyamphetamine aaron p. Moreover, compounds containing methanone linker between the aromatic rings and benzofuran at the c3 position had been investigated and reported as a uricosuricagent, a vasodilator, and a selective estrogen receptor modulator, such as benzbromarone and raloxifene fig.
A series of new benzofuran derivatives 3af, 5ae containing a heterocyclic. Expedited synthesis of benzofuran2carboxylic acids via. The first scientific conference the collage of sciences 20 table2. Pdf a convergent synthetic study of biologically active. Synthesis of 2substituted benzofuran derivatives by the. The mechanisms of the reactions and their use in the synthesis of biologically active substances are discussed. A simple and convenient approach was developed to the selective synthesis of 3. Biological evaluation in vitro revealed that only few compounds exerted concentrationdepended antiproliferative effects on tumour cell lines at micromolar concentrations. Synthesis of new benzofuran2carboxylic acid derivatives. Furan derivatives methods of synthesis of benzofuran derivatives benzofuran was first synthesized by perkin 3 from coumarin as shown in figure 2. A comparative study for the synthesis of symmetric 2,6di benzofuran 2yl4phenylpyridine derivatives 4ah as antibacterial agents, has been reported by two methods.
Initially the two derivatives of 21 benzofuran 2yl quinoline4carboxylic acid 3ab were synthesized, and it was found that they emit light in the blue region of the spectrum. Although several methods have been reported to synthesis benzofuran derivatives involving a transition metal catalyzed reaction, 1 most of them are achieved by the reaction of prefunctionalized substrates,2, 3, 4 while there are only limited examples of the construction of benzofuran derivatives by intermolecular coupling using simple phenols. A series of novel benzofuran derivatives containing biaryl moiety were designed and synthesized by the suzuki crosscoupling reactions. Khedr2 1therapeutical chemistry department, national research center, dokki, cairo, egypt 2welsh school of pharmacy, cardiff.
Synthesis of benzofuran derivatives and their evaluation of antimicrobial activity article pdf available in ejournal of chemistry 72 april 2010 with 600 reads how we measure reads. It is well known that vitamin e having chroman skeleton. Among them 24methoxy2methyl phenyl3hbenzofuro 3,2e benzofuran 29 was found to be most active with mic 3. The characterization of 25methoxy1benzofuran3yl n,n. An nhctriggered, transitionmetalfree strategy for the efficient synthesis of 2,3disubstituted benzofuran derivatives in moderate to excellent yields from aryl or alkyl aldehydes and oquinone methides has been developed. This method is robust and requires only 1 % catalyst compared to e. A facile electrochemical method for synthesis of new. Synthesis of oheterocycles benzofused oheterocycles synthesis of benzofurans. The reactions, performed in the presence of k 2 co 3, etohh 2 o and pdii complex as catalyst, gave the corresponding products in good to excellent yields. This methodology has also been shown as the key step in a collective total synthesis of hydroxylated benzofuran. Synthesis and evaluation of novel benzofuran derivatives. Synthesis, characterization, and anticancer activity of. Electrooxidation enables highly regioselective dearomative. This method provides an efficient and alternative approach to benzofurans which are very useful heterocyclic compounds with.
Benzofuran derivatives are of great interest in medicinal chemistry and have drawn considerable attention due to their diverse pharmacological profiles including anticancer activity. A mild and general route for the synthesis of benzofuran derivatives xiaocheng huang, yilin liu, yun liang, shaofeng pi, feng wang, jinheng li. Recently, benzofuran derivatives have attracted considerable interest for their versatile properties in chemistry and. A novel series of chalcones, 3aryl15bromo1 benzofuran. During a synthesis of coumarins to obtain new candidates for treating alzheimers disease ad, an unusual rearrangement of a benzopyran group to a benzofuran group occurred, offering a novel synthesis pathway of these benzofuran derivatives. This method provides an efficient and alternative approach to benzofurans which are very useful. Natural source, bioactivity and synthesis of benzofuran derivatives. Benzofuran derivatives possess several biological properties such as antiinflammatory, antimicrobial, antifungal, antihyperglycemic, analgesic, antiparasitic, and antitumor activities. Novel benzofuran derivatives bearing naryl piperazine moiety. Recent advancements 201417 in the benzofuran synthesis through iodocyclization have been summarized. Pdf an environmentally friendly route for the synthesis.
Design, synthesis, and biological evaluation of novel benzofuran. Activity of benzofuran derivatives many benzofuran compounds, including those isolated from plants as well as obtained by synthesis, exhibit a variety of biological activity. This methodology is appreciated in terms of chemoselectivity and mild reaction conditions. Radical cascade cyclization for synthesizing 3,4fused. A facile electrochemical method for synthesis of new benzofuran derivatives. 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. Ma and yuan recently disclosed a concise onepot synthesis of benzofuran derivatives using a benzyne precursor and a palladium0 source.
A novel strategy for the synthesis of benzofuran derivatives. The reported synthesis starting from 1trimethylsilyl1,3 butadiyne a 31 and protected 2iodophenol b, we have realized the synthesis of several orthosubstituted aryl diynes c,which produce various benzofuran derivatives. Benzofuran as a promising scaffold for the synthesis of. Pdf synthesis, antimicrobial and anticancer evaluation.
With this method, a large number of hydroxylated benzofuran derivatives with different substitution. Journal of chemical and pharmaceutical research, 2017, 95. 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. The broad range of clinical uses of benzofuran derivatives indicate the diverse. The methodology has been applied for the synthesis of more complex benzofuran derivatives, and may open. Jan 21, 2020 with this method, a large number of hydroxylated benzofuran derivatives with different substitution. A convergent synthetic study of biologically active benzofuran derivatives. Synthesis and biological activities of furan derivatives article pdf available in international journal of research in ayurveda and pharmacy 24. Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. Synthesis of benzofuran derivatives through cascade. Herein, we report a mild and broadly applicable method for the construction of complex benzofurylethylamine derivatives through a unique radical cyclization cascade. Natural source, bioactivity and synthesis of benzofuran derivatives article pdf available in rsc advances 947. It is essentially prepared via alkaline hydrolysis of khellin, a natural furanochromone isolated from ammi visnaga l. The catalytic ch coupling method employs cheap starting materials, exhibits a broad substrate scope, and liberates water as the only byproduct.
The cascade synthesis of benzofuran derivatives was conducted from the reaction of catechols and 1,3dicarbonyl compounds via oxidationmichael addition in the presence of laccase and scotf3sds. Pdf synthesis and biological activities of furan derivatives. A new method for synthesizing 3,4fused tricyclic 3alkylidene dihydrobenzofuran derivatives was developed. The successful use of various iodinating agents, bases, additives etc. A synthetic route to novel benzofuran fused phosphole derivatives 35 is described. Benzofuran is the parent of many related compounds with more complex structures. Arylidene derivatives as synthons in heterocyclic synthesis.
It is the parent of many related compounds with more complex structures. Owing to the biological importance of benzofurans, we herein, report the synthesis and biological testing of some benzofurans. The synthesis of benzofuran can be divided into phenol, benzoic acid and. All the intermediate and targeted molecules were confirmed by tlc, ir, nmr and mass data. Due to the presence of benzofuran moiety, they have a. Preliminary results show that 4 can be used as an emitter in oleds, illustrating the potential of these new compounds for optoelectronic applications. Method a follows nucleophilic substitution reaction of 2,6di benzofuran 2yl4phenylpyrilium tetrafluoroborate salt derivatives 3ah with ammonium acetate in ether at room.
Pdf synthesis of benzofuran derivatives and their evaluation of. This transformation can also tolerate a wide range of functional groups and achieve good efficiency in largescale synthesis under oxidantfree conditions. If the inline pdf is not rendering correctly, you can download the pdf file here. Synthesis and pharmacological examination of benzofuran.
An efficient method for the synthesis of dibenzofurans from oiododiaryl ethers is catalyzed by reusable pdc under ligandfree conditions. The substituted benzofurans are a class of chemical compounds based on the heterocyclyc and polycyclic compound benzofuran. Nheterocyclic carbenetriggered transitionmetalfree. The synthesis of novel series of benzofuran derivatives, containing barbitone moiety, 524substitutedphenyl5substituted1 benzofuran 2yl methylidenepyrimidin2,4,61h,3h,5htrione 4ai and thiobarbitone moiety, 524substitutedphenyl5substituted1 benzofuran 2ylmethylidene2thioxodihydropyrimidin4,61h, 5hdione 5ai have been. The benzofuran core is present in many biologically active natural products, which has made it a popular scaffold to explore when designing drugs 1,2,3,4. Usually these are called as benzofuran and isobenzofuran respectively figure 1. Derivatives from tyrosol simple and efficient synthesis of. Novel synthesis of benzosubstituted benzofurans via dielsalder reaction. Synthesis of elaborate benzofuran 2carboxamide derivatives through a combination of 8aminoquinoline directed ch arylation and transamidation chemistry michael oschmann y, linus johansson holm y, monireh pourghasemilati and oscar verho arrhenius laboratory, department of organic chemistry, stockholm university, se106 91 stockholm, sweden. Many medicines use the benzofuran core as a scaffold, but most commonly the term is used to refer to the simpler compounds in this class which include numerous psychoactive drugs, including stimulants, psychedelics and empathogens. Hence, different benzofurans having 4thiazolidinones have been synthesized for the purpose. Design, synthesis and evaluation of benzofuran acetamide scaffold as potential anticonvulsant agent ashok k. Similarly some of the benzofuran derivatives have shown very good antimicrobial activity and. General procedure for synthesis of benzofuran2carboxylic acid 2hydroxy1,1dimethylethylamides 3a, 3b a mixture of benzofuran2carboxylic acid ethyl esters 2a or 2b 0.
Synthesis, antimicrobial, and antioxidant activity of. Synthesis of o iododiaryl ether was achieved in one pot through sequential iodination and oarylation of phenol under mild reaction conditions. Design, synthesis and evaluation of benzofuranacetamide. Institute of biology and molecular patologies ibpm, department of. Numerous approaches to these important compounds have been developed over the years but novel general procedures for their synthesis are still important. Benzofurans are among the most popular structural units in bioactive natural products, however, the synthesis of such structures by radical cyclization cascade reactions is rare. An efficient synthesis of benzofuran derivatives under. Although the relative abundances for the remaining ions are quite similar, the. Similarly, chalcones, which are common substructures of numerous natural products belonging to the flavonoid class, feature strong anticancer properties. Benzofuran derivatives from alkynylsubstituted benzynes and. An environmentally friendly route for the synthesis of benzofurane derivatives using selective ring acylation of resorcinol. The synthesis and spectral properties of benzofuran.
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. Synthesis and characterization of some new pyrazoline. An efficient homogeneous catalytic enantioselective synthesis of. Supporting information synthesis and properties of. Pdf a facile electrochemical method for synthesis of new. 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.
A convenient metalfree cyclization of orthohydroxystilbenes into 2arylbenzofurans and 2arylnaphthofurans is mediated by hypervalent iodine reagents. The reaction with diols delivers benzofuran derivatives via dehydrative ch alkenylation and annulation reaction. A crystalline antioxidant extracted from yeast was shown to protect in vitro the erythrocytes of vitamin e deficient rats from hemolysis. 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 furan derivatives include the benzofused compounds which exist in two forms 1 benzofuran and 2 benzofuran. Various natural and synthetic benzofuran derivatives are found to possess diverse applications in the field of medicine. Benzofuran synthesis through iodocyclization reactions. 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.
Using the conditions established for cicerfurane16, 6 was. A series of benzofuran derivatives were designed and synthesized, and their inhibitory activites were measured against the sirt. In this manuscript the synthesis and biological activity of novel heterocyclic derivatives of benzofuran 2carboxamides 3aej and 6aef is presented. Treatment of propargyl iodophenol derivatives with a tethered alkene at the three contiguous positions under the radical cascade reaction conditions induced the reaction of the generated vinyl radical intermediates with the internal alkene, producing tricyclic 3alkylidene. Today, a large number of benzofuran based drugs are available on the market, including examples such as methoxsalen that is used against psoriasis and eczema, the antiarrhythmic medications amiodarone and. Natural and synthetic benzofuran derivatives are a class of important organic compounds with. Nichols departments of medicinal chemistry and pharmacognosy and pharmacology and toxicology, school of pharmacy and. Synthesis of new derivatives of benzofuran as potential.
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