Synthesis and reactions of benzofuran and benzothiophene. Sep 21, 2016 benzofuran derivatives are an important heterocyclic compounds that are possess vital biological activities such as antidepressant, anticancer, antiviral, antifungal, antioxidant, antipsychotic etc. Benzofuran is a fundamental structural unit in a variety of biologically active natural products as well as synthetic materials. Natural source, bioactivity and synthesis of benzofuran derivatives. Synthesis and reactions of benzofuran and benzothiophene, chemistry tutorial. Journal of chemical and pharmaceutical research, 2017, 95. Synthesis of some benzofuran and furocoumarin derivatives. Numerous synthesized benzofuran derivatives were found to be biologically active 7, 8, 9. Harmalkar, xuezhen xu, kyusic jang, kyeong lee bk21plus rfind team, college of pharmacy, dongguk universityseoul, goyang 410820, republic of korea a r t i c l e i n f o a b s t r a c t. Novel synthesis of benzofuran and indol2ylmethanamine. The possible reaction mechanism for the formation of intermediate substituted phenanthro9,10b benzofuran and pyreno4,5b benzofuran is firstly depicted. Institute of biology and molecular patologies ibpm, department of chemistry, sapienza university of rome, rome, italy.
It is the parent of many related compounds with more complex structures. Synthesis of benzofuran derivatives via different methods. The versatile reactivity of the trivalent phosphorus center of the parent bpbf offered access to a variety of derivatives by simple chemical modifications. Synthesis of new benzofuran2carboxylic acid derivatives. Entry enol ether 2 reactant alcohol used furan derivative 4 yield %a 1 63 2 68 3 64 4 54 5 53 6 51 7 52b 8 58 ayield refer to pure isolated product 4 from 2. 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. The synthesized compounds were tested against human liver carcinoma cell line hepg2 and. Therefore, the novel singlestep synthesis of compounds 3af, 5ae using a solid catalyst was performed. Pdf natural source, bioactivity and synthesis of benzofuran. Breaking the aromatic systems of electronrich arenes or heteroarenes provides threedimensional chemicals of high added value 1,2,3,4,5,6,7. Compounds 5s, 5r and 17b displayed the highest anticancer activity against ehrlich ascites.
In addition, several reports have pointed out the value of some synthetic benzofuran derivatives, containing a heterocyclic substituent linked at c2 of benzofuran nucleus, as antitumor agents. The excess dmf was distilled off and the reaction mixture was poured into ice. Many methodologies for the synthesis of benzofuran2carboxylic acid skeleton were developed and most of them are based on the reaction of salicylaldehydes with haloacetates followed by cyclization of formylphenoxyacetic acid derivatives intermediates 1117. Design, synthesis and evaluation of benzofuranacetamide scaffold as potential anticonvulsant agent ashok k. Mar 18, 2015 benzophospholo3,2bbenzofuran bpbf derivatives were studied as a new family of phospholecontaining. General procedure for the synthesis of n4oxothiazolidin3ylbenzofuran2carboxamide derivatives 6ag an equimolar mixture of schiff bases 4ae and thioacetic acid, and the catalytic amount of anhydrous zncl 2 was taken in dmf and refluxed for 68 h. For each compound series, a key intermediate bearing the oxazole4carboxylic acid methylester moiety was produced. All of the benzofuran derivatives have weak antiache activities compared with. Synthesis of benzofuran derivatives through cascade radical. A series of novel benzofuran scaffolds of amino pyrimidines 5a5s and azetidinones 17a17j were synthesized as potent biheterocyclic molecules. A series of new benzofuran derivatives 3af, 5ae containing a heterocyclic substituent linked to benzofuran nucleus at c2 were synthesized as potential antitumor agents. Synthesis of benzofuran derivatives via rearrangement and. Synthesis of some benzofuran and furocoumarin derivatives for possible biological activity synthesis of some benzofuran and furocoumarin derivatives for possible biological activity hishmat, o. Using stoichiometric diacetoxyiodobenzene in acetonitrile, desired products can be isolated in good yields.
We report on a novel synthesis towards benzofuran2ylmethanamine and indol2ylmethanamine derivatives by using orthomethoxy and orthonitro substituted phenylacetic acids as starting material, respectively. Structure activity relationships between these chalcone derivatives and starting material d1 demonstrated that benzofuran substituted chalcones showed more potent activities than. Physical properties of 3 benzofuran 2yl1phenyl pyrazoline derivatives 610. Methods for the synthesis of benzofuran derivatives. An efficient synthesis of benzofuran derivatives under. Structures of known 2substituted benzofuran derivatives and thiazolidinone derivatives with potential antitumor. Synthesis of anthra2,3ibenzofuran derivatives by cyclization of laccaic acid a derivatives and its reaction mechanism dingyu hu, yoshihiko shinoda, and shinichi nakatsuka t h e united graduate school of agricultural science, g i f u u n i v e r s i t y, yanagido, g i f u 5 0 1 1 1, japan a b s t r a c t. It is essentially prepared via alkaline hydrolysis of khellin, a natural furanochromone isolated from ammi visnaga l. Benzofuran is the parent of many related compounds with more complex structures.
A series of novel hybrid compounds between benzofuran and naryl piperazine have been synthesized and screened in vitro for antiinflammatory activity in lipopolysaccharide lpsstimulated raw264. For example, psoralen is a benzofuran derivative that occurs in several plants. For example, compound a 11, compound b 12 and compound c have been synthesized and evaluated as potent antitumor agents figure 1. Us5919955a combinatorial solid phase synthesis of a library. Volume 21, issue 12, december 2010, pages 14391442. Moracins aez in medicinal chemistry ravi naik, dipesh s. Synthesis, antimicrobial, and antioxidant activity of. A green method for synthesis of new benzofuran derivatives. Synthesis of benzofuran derivatives through cascade. These products were synthesized starting with 2bromoacetylbenzofuran 1. Moreover, the latter process has been adapted to accomplish the synthesis of indole, benzofuran, and benzothiophene derivatives 23, 27, and 28, respectively.
Design, synthesis, and biological evaluation of novel. Psoralen is a furocoumarin compound formed by fusion of furan with coumarin, which is naturally exists in some. These synthesized compounds were screened for in vivo anticancer activity. The mechanisms of the reactions and their use in the synthesis of biologically active substances are discussed. 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. General procedure for the synthesis of n4oxothiazolidin3yl benzofuran 2carboxamide derivatives 6ag an equimolar mixture of schiff bases 4ae and thioacetic acid, and the catalytic amount of anhydrous zncl 2 was taken in dmf and refluxed for 68 h. Siddiqui 1 department of chemistry 1, government institute of science, nagpur 440001, maharashtra, india. Recent advancements 201417 in the benzofuran synthesis through iodocyclization have been summarized. Synthesis, anticancer and molecular docking studies of.
Synthesis, characterization, and anticancer activity of. The reaction with diols delivers benzofuran derivatives via dehydrative ch alkenylation and annulation reaction. Recently, benzofuran derivatives have attracted considerable interest for their versatile properties in chemistry and. Synthesis and characterization of some new pyrazoline derivatives from chalcones bearing benzofuran moiety.
Cyclization conditions and reaction mechanism for t r a n s f o r m a t i o n of. Synthesis and characterization of some new pyrazoline. The furan derivatives include the benzofused compounds which exist in two forms 1 benzofuran and 2 benzofuran. Furan derivatives methods of synthesis of benzofuran derivatives benzofuran was first synthesized by perkin 3 from coumarin as shown in figure 2. Dubois, synthesis of polysubstituted benzofuran derivatives as novel inhibitors of parasitic growth, bioorg. We report on a novel synthesis towards benzofuran 2ylmethanamine and indol2ylmethanamine derivatives by using orthomethoxy and orthonitro substituted phenylacetic acids as starting material, respectively. Synthesis and antimicrobial activity of some novel derivatives of benzofuran, part 1. A facile and inexpensive synthesis of a series of novel methylenedioxybearing 2benzofuran2ylquinoline3carboxylic acid derivatives 3ah via the onepot reaction of ethyl 2chloromethyl6,7methylenedioxyquinoline3carboxylate 5 with various substituted salicylaldehydes 6ag as well as 2hydroxy1naphthaldehyde 6h is described substrate 5 was synthesized by the. Two novel phenanthro9,10b benzofuran and pyreno4,5b benzofuran modified twistacene derivatives 9 and 10 have been successfully synthesized via suzuki coupling and characterized. 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. Syn thesis and antimicrobial activity of benzofuran 2yl 3phenyl3methylcyclobutyl ketoxime derivatives. These compounds are important intermediates for the synthesis of a variety of synthetically. Development of dualacting benzofurans for thromboxane a2. Pdf synthesis of benzofuran derivatives and their evaluation of.
Furthermore, these continuous reactions could be achieved. Benzofuran synthesis through iodocyclization reactions. Synthesis of 2,3difunctionalized benzofuran derivatives through. Titaniumiii chloride mediated synthesis of furan derivatives 425 table 1. The substituted benzofurans are a class of chemical compounds based on the heterocyclyc and polycyclic compound benzofuran. Synthesis of oheterocycles benzofused oheterocycles synthesis of benzofurans. The structure of this compound was determined as benzofuran derivative. Synthesis, characterization, and anticancer activity of new. Design, synthesis and evaluation of benzofuran acetamide scaffold as potential anticonvulsant agent ashok k. Benzofuran is basically a heterocyclic compound comprising of fused benzene and furan ring. Natural source, bioactivity and synthesis of benzofuran derivatives article pdf available in rsc advances 947. Davood nematollahi, davood habibi, mohammad rahmati, mohammad rafiee. The three patterns of reactivity observed for the o. Benzofuran derivatives possess several biological properties such as antiinflammatory, antimicrobial, antifungal, antihyperglycemic, analgesic, antiparasitic, and antitumor activities.
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. Derivatives from tyrosol simple and efficient synthesis of. The synthesis and spectral properties of benzofuran. Substituted benzofurans also posses other applications such as fluorescent sensor, antioxidants, oxidant, brightening agents and in other field of chemistry and agriculture. Pdf a series of new benzofuran derivatives 3af, 5ae containing a heterocyclic substituent linked to. Design, synthesis and evaluation of benzofuranacetamide. Natural and synthetic benzofuran derivatives are a class of important organic compounds with a broad range of biological activities, such as antioxidant, antiin. All the newly synthesized compounds were confirmed by spectral studies. Similarly some of the benzofuran derivatives have shown very good antimicrobial activity and. The results demonstrated that derivative 16 not only had inhibitory effect on the generation of no ic50 5. Benzofuran is maillard produced present in roasted coffee aroma. The furan derivatives include the benzofused compounds which exist in two forms 1benzofuran and 2benzofuran. The possible mechanism of the novel rearrangement was also discussed. A crystalline antioxidant extracted from yeast was shown to protect in vitro the erythrocytes of vitamin e deficient rats from hemolysis.
Two novel phenanthro9,10bbenzofuran and pyreno4,5bbenzofuran modified twistacene derivatives 9 and 10 have been successfully synthesized via suzuki coupling and characterized. Titanoceneiii chloride mediated synthesis of furan derivatives. Synthesis and properties of benzophospholo3,2bbenzofuran. Synthesis and biological evaluation of new benzofuran carboxamide. Exploitation of donoracceptor cyclopropanes and nsulfonyl 1. The obtained ethyl halobenzofuran2carboxylates 2a and 2b were next subjected to the reaction with 2amino2methylpropan1ol in the presence of ammonium chloride. Herein, we report a mild and broadly applicable method for the construction of complex benzofurylethylamine derivatives through a unique radical cyclization cascade. In the literature, there are few studies on the synthesis of khellinone derivative chalcone compounds. The successful use of various iodinating agents, bases, additives etc. A facile electrochemical method for synthesis of new. Benzofuran derivatives are an important heterocyclic compounds that are possess vital biological activities such as antidepressant, anticancer, antiviral, antifungal, antioxidant, antipsychotic etc. A novel series of chalcones, 3aryl15bromo1 benzofuran.
Issn 22293566 synthesis and biological activity of furan derivatives verma anupam, pandeya s. Institute of biology and molecular patologies ibpm, department of. The present invention relates to a process for the generation of a plurality of different benzofuran derivatives, and to the use of said benzofuran derivatives to search for novel classes of compounds and individual compounds possessing selected properties for pharmaceutical applications. It may also be formed during other uses of coal or oil. 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. Pdf 2acetyl benzofuran 1 was synthesized by refluxing. Benzophospholo3,2bbenzofuran bpbf derivatives were studied as a new family of phospholecontaining. The synthesis and antimicrobial activity of some novel 11benzofuran2yl2 mesitylethanone derivatives eur. Benzofuran as a promising scaffold for the synthesis of. 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. A convenient metalfree cyclization of orthohydroxystilbenes into 2arylbenzofurans and 2arylnaphthofurans is mediated by hypervalent iodine reagents. The present study deals with the synthesis of some substituted pyrazolines with.
This methodology is appreciated in terms of chemoselectivity and mild reaction conditions. In addition, hydrolysis of one of the nsulfonyl derivatives offered the. 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. These compounds are important intermediates for the synthesis of a variety of. Usually these are called as benzofuran and isobenzofuran respectively figure 1. Synthesis of anthra2,3i benzofuran derivatives by cyclization of laccaic acid a derivatives and its reaction mechanism dingyu hu, yoshihiko shinoda, and shinichi nakatsuka t h e united graduate school of agricultural science, g i f u u n i v e r s i t y, yanagido, g i f u 5 0 1 1 1, japan a b s t r a c t. Due to the presence of benzofuran moiety, they have a. 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. Owing to the biological importance of benzofurans, we herein, report the synthesis and biological testing of some benzofurans. The structures of all compounds were established on the basis of analytical and spectral data.
It is well known that vitamin e having chroman skeleton have a. The possible reaction mechanism for the formation of intermediate substituted phenanthro9,10bbenzofuran and. Realizing the importance of benzofuran derivatives in the synthesis of various drug sources reported in few classical methods such as, cyclocondensation of salicylaldehyde with. The catalytic ch coupling method employs cheap starting materials, exhibits a broad substrate scope, and liberates water as the only byproduct. Similarly, chalcones, which are common substructures of numerous natural products belonging to the flavonoid class, feature strong anticancer properties. The benzofuran derivatives are naturally occurring and possess many.
In addition to the above, benzofuran derivatives possess a wide range of biological activities such as antimicrobial, antitumor, antiinflammatory 68. Synthesis and biological evaluation of new benzofuran. The first scientific conference the collage of sciences 20 table2. Synthesis and biological activities of some benzofuran. The benzofuran substituted chalcones showed anticancer activity on pc3 and mcf7 cell lines. Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. Novel benzofuran derivatives bearing naryl piperazine moiety.
General procedure for synthesis of benzofuran2carboxylic acid 2hydroxy1,1dimethylethylamides 3a, 3b a mixture of benzofuran2carboxylic acid ethyl esters 2a or 2b 0. This colourless solid is a component of the coal tar. Various natural and synthetic benzofuran derivatives are found to possess diverse applications in the field of medicine. Benzofuran derivatives are of great interest in medicinal chemistry and have drawn considerable attention due to their diverse pharmacological profiles including anticancer activity. Shin, microwaveassisted parallel synthesis of benzofuran2carboxamide derivatives bearing antiinflammatory, analgesic and antipyretic agents, tetrahedron lett. Furthermore, the 2methylbenzofuran derivatives 9 were synthesized using. The diversityoriented synthetic route was also developed to allow facile access to bpbfs with a.
A facile electrochemical method for synthesis of new benzofuran derivatives. Electrooxidation enables highly regioselective dearomative. The methodology has been applied for the synthesis of more complex benzofuran derivatives, and may open. Expanded benzofurandecorated twistacene derivatives. An efficient synthesis of benzofuran derivatives under conventionalnon.
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