Numerous synthesized benzofuran derivatives were found to be biologically active 79. For the directed ch arylation reactions, pd catalysis was used to install a wide range of aryl and heteroaryl substituents at the c3 position of the benzofuran. The front cover picture was provided by tsuyoshi mita and co. Recent advancements 201417 in the benzofuran synthesis through iodocyclization have been summarized. It is essentially prepared via alkaline hydrolysis of khellin, a natural furanochromone isolated from ammi visnaga l. Novel benzofuran derivatives bearing naryl piperazine moiety. Benzofuran synthesis through iodocyclization reactions. Institute of biology and molecular patologies ibpm, department of chemistry, sapienza university of rome, rome, italy. High reaction efficiency, mild conditions, broad substrate scope, and good functional group tolerance are the features of this protocol. Numerous approaches to these important compounds have been developed over the years but novel general procedures for their synthesis are still important. Ma and yuan recently disclosed a concise onepot synthesis of benzofuran derivatives using a benzyne precursor and a palladium0 source.
Synthesis and reactions of new derivatives of furo3,2bpyrrole. Benzofuran derivatives from alkynylsubstituted benzynes and. Pdf synthesis and biological activities of furan derivatives. As a service to our customers we are providing this early version of the manuscript. The obtained ethyl halobenzofuran2carboxylates 2a and 2b were next subjected to the reaction with 2amino2methylpropan1ol in the presence of ammonium chloride. The main advantages of this synthetic strategy include the use of simple, inexpensive, nontoxic, and readily accessible starting materials, and its pot, atom. Design, synthesis, and biological evaluation of novel benzofuran. This picture represents that ketoalkenes are automatically converted to tramadol. Initially the two derivatives of 21benzofuran2yl quinoline4carboxylic acid 3ab were synthesized, and it was found that they emit light in the blue region of the spectrum. Synthesis of benzofuran derivatives via intramolecular cyclization of corresponding aryl propargyl ethers have witnessed rapid and comprehensive development in recent years. Supporting information synthesis and properties of.
The benzofuran scaffold is a heterocyclic motif that consists of a fused benzene and furan ring, and many different synthetic strategies have been used in the past to introduce substituents on these two parts scheme 1a,b 8,9,10. Pdf synthesis of benzofuran derivatives and their evaluation of. This colourless solid is a component of the coal tar. Natural source, bioactivity and synthesis of benzofuran. School of dentistry at niigata, the nippon dental university, hamaura. Onepot synthesis of novel symmetric 1,5dibenzofuran2. Dec 27, 20 chandrashekar a, eswarappa b, bodke yd, venkatesh kb, raghu n, shivakumar mc, peethambar sk, telkar s 20 5phenyl1benzofuran2yl derivatives. The successful use of various iodinating agents, bases, additives etc. Wrzesniewska institute of organic technology, west pomeranian university of technology, 42 aleja piastow, 71065 szczecin, poland correspondence should be addressed to h. This method provides an efficient and alternative approach to benzofurans which are very useful heterocyclic compounds with. Znotf 2 catalyzed the cyclization of propargyl alcohols with anilines and phenols in toluene at 100c without additive and gave various indole and benzofuran products with different structures. Synthesis and characterization of some new pyrazoline derivatives from chalcones bearing benzofuran moiety. Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. Methods for the synthesis of benzofuran derivatives.
An efficient route to carbazoles and dibenzofurans has been developed. Results and discussion the first set of experiments was directed towards the onepot protectioncouplingcyclization of bromohydroquinone 6, figure 3. In continuation of our work in the development of facile and efficient methodologies using ionic liquids and various organic transformations, in this work we wish to propose an effective strategy for the synthesis of 2acetylcarbo ethoxy benzofuran derivatives. Synthesis and reactions of benzofuran and benzothiophene, chemistry tutorial.
The synthesis of benzofuran can be divided into phenol, benzoic acid and. Synthesis and pharmacological examination of benzofuran. The synthesis of the benzofuran derivatives is shown in scheme 1. Synthesis and biological activities of furan derivatives article pdf available in international journal of research in ayurveda and pharmacy 24. Synthesis and biological activities of some benzofuran derivatives with 4thiazolidinone moiety.
Synthesis and properties of benzophospholo 3,2bbenzofuran derivatives motonobu takahashi, koji nakano, kyoko nozaki department of chemistry and biotechnology, graduate school of engineering, the university of tokyo, 731 hongo, bunkyoku, tokyo 18656, japan. The furan derivatives include the benzofused compounds which exist in two forms 1benzofuran and 2benzofuran. Hence, different benzofurans having 4thiazolidinones have been synthesized for the purpose. For example, psoralen is a benzofuran derivative that occurs in several plants. Benzofuran derivatives from alkynylsubstituted benzynes. A facile electrochemical method for synthesis of new. Nichols departments of medicinal chemistry and pharmacognosy and pharmacology and toxicology, school of pharmacy and. In the literature, there are few studies on the synthesis of khellinone derivative chalcone compounds. Synthesis of 2substituted benzofuran derivatives by the. A straightforward synthesis of indole and benzofuran.
The results demonstrated that derivative 16 not only had inhibitory effect on the generation of no ic50 5. Numerous synthesized benzofuran derivatives were found to be biologically active 7, 8, 9. Due to the presence of benzofuran moiety, they have a. 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. In this reaction, both the benzene and furan rings were simultaneously constructed, whereas the pyrone moiety of the kojic acid or maltol was deconstructed and then reorganized into the benzene ring as a six. Us7015246b2 us10471,444 us47144404a us7015246b2 us 7015246 b2 us7015246 b2 us 7015246b2 us 47144404 a us47144404 a us 47144404a us 7015246 b2 us7015246 b2 us 7015246b2 authority us united states prior art keywords hydrogen alkyl group optionally substituted halogen prior art date 20010329 legal status the legal status is an assumption and is not a legal. Design, synthesis and evaluation of benzofuranacetamide. Khedr2 1therapeutical chemistry department, national research center, dokki, cairo, egypt 2welsh school of pharmacy, cardiff university, uk. An efficient synthesis of benzofuran derivatives under. Synthesis and evaluation of novel benzofuran derivatives. 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.
Herein, we present a short and highly modular synthetic route that involves 8aminoquinoline directed ch arylation and transamidation chemistry, and which enables access to a wide range of elaborate benzofuran2carboxamides. Among them 24methoxy2methyl phenyl3hbenzofuro 3,2e benzofuran 29 was found to be most active with mic 3. 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. Owing to the biological importance of benzofurans, we herein, report the synthesis and biological testing of some benzofurans. Pdf a series of new benzofuran derivatives 3af, 5ae containing a heterocyclic substituent linked to benzofuran nucleus at c2 were. Further it was planned to modify the carboxylic acid functionality by electron donor. Synthesis and biological evaluation of new benzofuran carboxamide. Natural and synthetic benzofuran derivatives are a class of important organic compounds with.
The mechanisms of the reactions and their use in the synthesis of biologically active substances are discussed. Derivatives from tyrosol simple and efficient synthesis of. Synthesis of oheterocycles benzofused oheterocycles synthesis of benzofurans. They revealed that various ketoalkenes underwent a co. Similarly some of the benzofuran derivatives have shown very good antimicrobial activity and. Among the various ionic resins attempted, amberlyst15 in peg400 was the choice of selection for the synthesis of 3benzoyl5hydroxy benzofuran and naphtho1,2bfuran derivatives at room temperature in an environmentally friendly method. Synthesis of benzofuran derivatives via rearrangement and their inhibitory activity on acetylcholinesterase xiang zhou 1, miao li 2, xiaobing wang 1, tao wang 2 and lingyi kong 1, 1 department of natural medicinal chemistry, china pharmaceutical university, 24 tong jia xiang, nanjing 29, china. Jan 15, 2020 in summary, we have outlined a modular synthetic strategy that can be used to prepare a diverse set of c3substituted, benzofuran 2carboxamide derivatives, from a simple benzofuran precursor in only three synthetic steps.
Synthesis and reactions of benzofuran and benzothiophene. Synthesis of oiododiaryl ether was achieved in one pot through sequential iodination and oarylation of phenol under mild reaction conditions. Synthesis of chalcone derivatives of benzo furan as. A series of benzofuran derivatives were designed and synthesized, and their inhibitory activites were measured against the sirt. Chandrashekar a, eswarappa b, bodke yd, venkatesh kb, raghu n, shivakumar mc, peethambar sk, telkar s 20 5phenyl1benzofuran2yl derivatives. This article is covered the methods of synthesis of benzofuran and its derivatives, structural activity relationship and pharmacological activities so it is an effort to highlight the importance of the benzofuran in the present context and promise they hold for the future. Synthesis of potent antitumor and antiviral benzofuran. Pyrazole derivatives 11 were prepared by the reaction of azlactone 9 with derivatives 10. Benzofuran is basically a heterocyclic compound comprising of fused benzene and furan ring. Synthesis of new benzofuran2carboxylic acid derivatives. Natural source, bioactivity and synthesis of benzofuran derivatives yuhang miao, abcd yuheng hu,abcd jie yang,abcd teng liu,abcd jie sun abcd and xiaojing wangabcd benzofuran compounds are a class of compounds thatare ubiquitous in nature. Synthesis of elaborate benzofuran2carboxamide derivatives.
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. The present study deals with the synthesis of some substituted pyrazolines with. Synthesis and antimicrobial activity of benzofuran 2yl3. A straightforward synthesis of indole and benzofuran derivatives. The furan derivatives include the benzofused compounds which exist in two forms 1 benzofuran and 2 benzofuran. This method provides an efficient and alternative approach to benzofurans which are very useful heterocyclic compounds with biological and pharmacological potentials. Synthesis and cytotoxicity screening of some novel. H arylation and transamidation chemistry, and which enables access to a wide range of elaborate benzofuran 2carboxamides. Onepot synthesis of novel symmetric 1,5dibenzofuran2yl.
Some of these synthesized compounds were evaluated for cytotoxicity activity against hepg2 liver carcinoma cell line and hela cervix carcinoma cell. Benzofuran as a promising scaffold for the synthesis of antimicrobial. Synthesis of difluoroalkylated benzofuran, benzothiophene. Jan 01, 2008 read a straightforward synthesis of indole and benzofuran derivatives, tetrahedron on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. Synthesis of benzofuran derivatives through cascade. Using the conditions established for cicerfurane16, 6 was. 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.
Synthesis and biological activities of some benzofuran. The key intermediate 4 the key intermediate 4 hydroxy6methylcoumarin b was prepared from p cresol and malonic acid using zncl 2 as the. The first scientific conference the collage of sciences 20 synthesis and characterization of some new pyrazoline derivatives from chalcones bearing benzofuran moiety. The present work describes the synthesis and characterization of six new dyes.
The benzofuran derivatives are naturally occurring and possess many. This is a pdf file of an unedited manuscript that has been accepted for publication. 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. A convenient metalfree cyclization of orthohydroxystilbenes into 2arylbenzofurans and 2arylnaphthofurans is mediated by hypervalent iodine reagents. The synthesis and spectral properties of benzofuran. The substituted benzofurans are a class of chemical compounds based on the heterocyclyc and polycyclic compound benzofuran. Reactions were carried out under microwave irradiation or at classical heating. The broad range of clinical uses of benzofuran derivatives indicate the diverse.
Synthesis and reactions of new derivatives of furo3,2b. Research article synthesis of new benzofuran2carboxylic acid derivatives m. Novel synthesis of benzosubstituted benzofurans via dielsalder reaction. H arylation reactions, pd catalysis was used to install a wide range of aryl and heteroaryl substituents at the c3 position of the. Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4 methy1enedioxyamphetamine aaron p. The cyclization of propargyl alcohols and amides gave oxazoles. Pdf 2acetyl benzofuran 1 was synthesized by refluxing salicylaldehyde and dry chloroacetone in presence of potassium carbonate. A series of new pyrazole, thiazole and thiazolinone derivatives incorporated into benzofuran were synthesized by using 3benzofuran2yl1phenyl1hpyrazol4carboxaldehyde as starting material.
Benzofuran is the parent of many related compounds with more complex structures. Intramolecular cyclization of aryl propargyl ethers. The anticancer activities of novel synthesized derivatives were evaluated against. 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.
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. The obtained ethyl halo benzofuran 2carboxylates 2a and 2b were next subjected to the reaction with 2amino2methylpropan1ol in the presence of ammonium chloride when this process was carried out in boiling methanol for 16 hours the target benzofuran 2carboxylic acid 2hydroxy1,1dimethylethylamides 3a and 3b were obtained in moderate yi. Synthesis and characterization of some new pyrazoline. For this synthesis we have condensed the substituted salicylaldehydes 1 with.
Synthesis, antimicrobial, and antioxidant activity of. This expedient approach enables the synthesis of a range of polycyclic benzofurans that would otherwise be difficult to prepare. Design, synthesis and evaluation of benzofuranacetamide scaffold as potential anticonvulsant agent. Synthesis of benzofuran derivatives via rearrangement and their inhibitory activity on acetylcholinesterase xiang zhou 1, miao li 2, xiaobing wang 1, tao wang 2 and lingyi kong 1, 1 department of natural medicinal chemistry, china pharmaceutical. Using stoichiometric diacetoxyiodobenzene in acetonitrile, desired products can be isolated in good yields. 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. Journal of chemical and pharmaceutical research, 2017, 95. 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. Natural source, bioactivity and synthesis of benzofuran derivatives. Synthesis of benzofuran derivatives via rearrangement and.
It may also be formed during other uses of coal or oil. Synthesis and biological activities of furan derivatives. Furan derivatives methods of synthesis of benzofuran derivatives benzofuran was first synthesized by perkin 3 from coumarin as shown in figure 2. In addition to the above, benzofuran derivatives possess a wide range of biological activities such as antimicrobial, antitumor, antiinflammatory 68. This catalyst system resulted in excellent yields in short reaction times and high selectivity. Institute of biology and molecular patologies ibpm, department of.
Usually these are called as benzofuran and isobenzofuran respectively figure 1. Substituents at the benzene moiety often originate from the synthetic precursor used to construct the benzofuran scaffold. 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 hydrazinolysis of 1 was prepared by carbohydrazide 2, which subsequently reacted with aldehydes to form of derivatives 3. We have discussed here significant biological properties of these derivatives such as antitumor, antimicrobial, antihyperglycemic, analgesic, antiinflammatory, antiviral, antipyretic activities etc. Benzofuran is an important scaffold in the several biologically active organic compounds, and the development of an efficient method to construct it and its derivatives is one of the major topics in organic synthesis. Read a straightforward synthesis of indole and benzofuran derivatives, tetrahedron on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips.248 555 13 1247 1298 372 245 622 901 1182 117 312 475 201 832 685 958 1074 1434 579 922 807 831 322 103 1392 391 295 1314 1472 228 136 478 1247