These products were synthesized starting with 2bromoacetylbenzofuran 1. A novel and efficient method for the synthesis of difluoroalkylated benzofuran, benzothiophene, and indole derivatives via palladiumcatalyzed aryldifluoroalkylation of 1,6enynes with ethyl difluoroiodoacetate and arylboronic acids has been established. A synthetic route to novel benzofuranfused phosphole derivatives 35 is described. Benzofuran derivatives are an important heterocyclic compounds that are possess vital biological activities such as antidepressant, anticancer, antiviral, antifungal, antioxidant, antipsychotic etc. Download synthesis and evaluation of 41 benzofuran2 yl1,3. Synthesis, antimicrobial, and antioxidant activity of. The present work describes the synthesis and characterization of six new dyes. Read online synthesis and evaluation of 41 benzofuran2 yl1,3. Natural source, bioactivity and synthesis of benzofuran.
Benzofuran derivatives, especially naphthofurans, constitute a. Ma and yuan recently disclosed a concise onepot synthesis of benzofuran derivatives using a benzyne precursor and a palladium0 source. 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. A versatile novel synthesis of benzofuran and related compounds. Toxicological profile for 2,3benzofuran supplements the profile that was released in 1992. In the second step, compound 3 was synthesized by the resorcinol ring post coupling. Onestep regioselective synthesis of benzofurans from phenols and. Pdf 2acetyl benzofuran 1 was synthesized by refluxing salicylaldehyde and. Us6828448b2 methanesulphonamidobenzofuran, preparation. Benzofuran compounds such as 6apb and 5apb are similar to ecstasy and amphetamines like speed, so risks may include dilated pupils, tingling feelings, tightening of the jaw muscles, raised body temperature, increased blood pressure and heart rate, and insomnia. Benzofuran is one of the most important fused heterocycles, containing a benzene ring fused to a furan ring. Benzofuran compounds are often analogues of mdxx and tryptamine compounds where a benzofuran ring has replaced the benzodioxole ring structure or indole ring respectively. Journal of chemical and pharmaceutical research, 2017, 95.
A ligandfree cubr catalyzed couplingcyclization of terminal alkynes 83 with ntosylhydrazones 82. Synthesis and biological activities of some benzofuran. Thus, benzofuran moiety can be taken as lead compound for the synthesis of novel derivatives with a variety of biological activities. Biological and medicinal significance of benzofuran. Synthesis of oheterocycles benzofused oheterocycles synthesis of benzofurans. Files are available under licenses specified on their description page.
Synthesis of new derivatives of benzofuran as potential. Using stoichiometric diacetoxyiodobenzene in acetonitrile, desired products can be isolated in good yields. Pdf benzofuran synthesis through iodocyclization reactions. 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.
Medicinal chemists are actively involved in the synthesis of benzofuran ring containing molecules due to its clinical importance. Benzofuran is basically a heterocyclic compound comprising of fused benzene and furan ring. Synthesis of benzofuran and indole derivatives catalyzed by. Efficient microwaveassisted onepot threecomponent synthesis of 2,3disubstituted benzofurans under sonogashira conditions. Synthesis of new benzofuran2carboxylic acid 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. Benzofuran as a promising scaffold for the synthesis of. Transition metalcatalyzed benzofuran synthesis by xiao. 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. Transition metalcatalyzed heterocycle synthesis series provides an overview of benzofuran, describing properties of these heterocycle compounds and the traditional synthetic procedures used for them.
With this method, a large number of hydroxylated benzofuran derivatives with different substitution. Synthesis and reactions of benzofuran and benzothiophene, chemistry tutorial. Benzofuran synthesis through iodocyclization reactions. A series of new benzofuran derivatives 3af, 5ae containing a heterocyclic substituent linked to benzofuran nucleus at c2 were synthesized as potential antitumor agents. This modified procedure yielded 98% of benzofuran product scheme. Benzofuran is the parent of many related compounds with more complex structures. Pdf synthesis of benzofuran derivatives and their evaluation of. The substituted benzofurans are a class of chemical compounds based on the heterocyclyc and polycyclic compound benzofuran. Chanlamtype cn crosscoupling reactions under base and ligand free cu izeolite catalysis. Benzofuran is maillard produced present in roasted coffee aroma. Takashi hirota, hiroko fujita, kenji sasaki, tetsuto namba, shohei hayakawa. A convenient metal free cyclization of orthohydroxystilbenes into 2arylbenzofurans and 2arylnaphthofurans is mediated by hypervalent iodine reagents. Synthesis and reactions of benzofuran and benzothiophene. Substituted benzofurans also posses other applications such as fluorescent sensor, antioxidants, oxidant, brightening agents and in other field of chemistry and agriculture.
Benzofuran derivatives from alkynylsubstituted benzynes. These compounds showed optical and electrochemical properties that differ from their benzothiophene analog. For example, psoralen is a benzofuran derivative that occurs in several plants. Methods for the synthesis of benzofuran derivatives. A complex benzofuran derivative is constructed by a unique free radical cyclization cascade, which is an excellent method for the synthesis of a series of di. Syn thesis and antimicrobial activity of benzofuran2yl 3phenyl3methylcyclobutyl ketoxime derivatives. This 2acetylbenzzofuran after chlorination gives chloroacetylbenzofuran.
Its derivatives are the scaffold of many natural products and several complex structures. Onestep regioselective synthesis of benzofurans from phenols. Hence, different benzofurans having 4thiazolidinones have been synthesized for the purpose. For each compound series, a key intermediate bearing the oxazole4carboxylic acid methylester moiety was produced. A versatile novel synthesis of benzofuran and related. The catalyst was prepared by an ion exchange of nh4y zeolites using a.
Chandrashekar a, eswarappa b, bodke yd, venkatesh kb, raghu n, shivakumar mc, peethambar sk, telkar s 20 5phenyl1benzofuran2yl derivatives. Recent advances find, read and cite all the research you need on researchgate. This method provides an efficient and alternative approach to benzofurans which are very useful heterocyclic compounds with. Salicylaldehyde upon treatment with chloroacetone in presence of anhydrous potassium carbonate give 2acetylbenzofuran. All books are in clear copy here, and all files are secure so dont worry about it. Novel methods for constructing benzofuran rings have been discovered in recent years. The palladium catalyzed cross coupling of 5iodoresorcinol derivative 40 with 2trimethylstannyl benzofuran 43 produced complex 44 by forming the key benzofuranresorcinol bond scheme 3. Benzofuran compound benzos effects and risks frank. Synthesis and antimicrobial activity of some novel derivatives of benzofuran, part 1. Pdf on dec 29, 2017, saurabh mehta and others published. The corresponding compound on treatment with various aldehydes to give different derivative. This compound is a synthesis intermediate, in particular for the preparation of dronedarone.
Mcmurry reaction approach for benzofuran synthesis. Synthesis of benzofuran derivatives via different methods. The characterization of 62aminopropylbenzofuran and. Most approaches for the synthesis of indole and benzofuran. Synthesis of difluoroalkylated benzofuran, benzothiophene. The drug hydroxyurea destroys the free radical required for the enzyme. Synthesis of 2substituted benzofurans catalyzed by copperfree palladium zeolites. This chloroacetylbenzofuran on treatment with urea in ethanol gives 4 1benzofuran2yl 1, 3oxazole2amine. Synthesis of oiododiaryl ether was achieved in one pot through sequential iodination and oarylation of phenol under mild reaction conditions. The results demonstrated that derivative 16 not only had inhibitory effect on the generation of no ic50 5. Benzofuran derivatives can be synthesized through the sequential michael addition and cyclization of 1,3. It is the parent of many related compounds with more complex structures. The 5 and 6 isomers compounds 2 and 3 gave virtually identical retention times and could not be resolved under the conditions utilized.
The mechanisms of the reactions and their use in the synthesis of biologically active substances are discussed. On the other hand, benzofuran chromophore with high photoluminescence pl and quantum efficiencies found wide application as organic electroluminescent devices 11 and chemosensors 14, 15. A convenient metalfree cyclization of orthohydroxystilbenes into 2arylbenzofurans and 2arylnaphthofurans is. Benzofuran as a promising scaffold for the synthesis of antimicrobial and antibreast cancer agents. Pdf on dec 29, 2017, saurabh mehta and others published benzofuran synthesis through iodocyclization reactions. A ligandfree cubrcatalyzed couplingcyclization of terminal alkynes 83 with ntosylhydrazones 82. Benzofurans and indoles are key moieties in many natural products. However, ketones are rarely used in this reaction because of their low nucleophilicities. Many of the clinically approved drugs are synthetic and naturally occurring substituted benzofuran derivatives containing mono and fused benzofuran ring. 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. An efficient method for the synthesis of dibenzofurans from oiododiaryl ethers is catalyzed by reusable pdc under ligand free conditions. Syn thesis and antimicrobial activity of benzofuran 2yl 3phenyl3methylcyclobutyl ketoxime derivatives.
Benzofuran itself is a colorless liquid obtained from coal tar. Structure, properties, spectra, suppliers and links for. Toxicological profiles are developed in response to the superfund amendments and reauthorization act sara of 1986, which amended the comprehensive environmental response, compensation, and liability act of 1980 cercla or superfund. Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. We have also attempted pdcatalyzed couplings with the 5bromobenzofurans 16 and 17 prepared by our benzofuran synthesis to illustrate how our benzofurans can be. All structured data from the file and property namespaces is available under the creative commons cc0 license. Preliminary results show that 4 can be used as an emitter in oleds, illustrating the potential of these new compounds for optoelectronic applications. 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. This methodology has also been shown as the key step in a collective total synthesis of hydroxylated benzofuran. Novel synthesis of benzofuran and indol2ylmethanamine. High reaction efficiency, mild conditions, broad substrate scope, and good functional group tolerance are the features of this protocol. This colourless solid is a component of the coal tar.
Heravi, vahideh zadsirjan, in advances in heterocyclic chemistry, 2015. Synthesis of 52aminopropylbenzofuran 2 and 72aminopropylbenzofuran 4. Review on synthetic routes for synthesis of benzofuranbased. A synthetic route to novel benzofuran fused phosphole derivatives 35 is described. We report on a novel synthesis towards benzofuran 2ylmethanamine and indol2ylmethanamine derivatives by using orthomethoxy and orthonitro substituted phenylacetic acids as starting material, respectively. The obtained ethyl halobenzofuran2carboxylates 2a and 2b were next subjected to the reaction with 2amino2methylpropan1ol in the presence of ammonium chloride. The structures of all compounds were established on the basis of analytical and spectral data. Therefore, a practical and flexible avenue to free hydroxylated benzofurans with.
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