Among 31tested compounds, some of them showed good activity selective. Herein, we report a mild and broadly applicable method for the construction of complex benzofurylethylamine derivatives through a unique radical cyclization cascade. 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. Pdf 2acetyl benzofuran 1 was synthesized by refluxing salicylaldehyde and dry chloroacetone in presence of potassium carbonate. Most of the benzofurans are research chemicals, most commonly stimulants and entactogens, and are fairly new. Synthesis of benzofuran derivatives through cascade. Synthesis of oheterocycles benzofused oheterocycles synthesis of benzofurans. Then, the reaction mixture was stirred at room temperature to obtain benzofuran2carbohydrazide as a. Institute of biology and molecular patologies ibpm, department of chemistry, sapienza university of rome, rome, italy. A palladiumcatalyzed carbonylative intramolecular synthesis of benzofuran 23hones from 2hydroxybenzyl alcohols has been developed. An efficient synthesis of functionalized benzofurans is achieved under mild and metalfree conditions from stable paraquinone methides by treatment with phosphine, acyl chloride, and a base. Benzofuran coumarone, a heterocyclic compound consisting of fused benzene and furan rings, has been identified as a privileged structure in medicinal chemistry. Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4 methy1enedioxyamphetamine aaron p.
The benzofuran biphenyls described in this paper were prepared according to the synthetic scheme 1. Synthesis and antimicrobial activity of furochromone, benzofuran. 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. Pdf benzofuran synthesis through iodocyclization reactions.
In this procedure, formic acid was utilized as the co source, and various benzofuran23hone derivatives were obtained in moderate to good yields. By this method it is possible to obtain these tetracyclic systems not only in the form of one isomer but also to convert them from one to the other. Synthesis of 62aminopropylbenzofuran 3 and 42aminopropylbenzofuran 1 in accordance with journal policy, exact experimental details are not provided, but are outlined in figure 2. Catalyzed skeletal rearrangement of spirotricyclic. A synthetic route to novel benzofuran fused phosphole derivatives 35 is described. Synthesis of benzofuran2carbohydrazide 4 31 the mixture of hydrazine hydrate 15 ml and ethyl benzofuran2carboxylate 0. Benzofurans are chemical compounds which contain a benzofuran ring in their structure. This compound was first reported in 1992 to evaluate its affinity for serotonin receptors in rats and for possible use in the design of serotonin receptor ligands 2. In this procedure, formic acid was utilized as the co source, and various benzofuran 23hone derivatives were obtained in moderate to good yields. The cyclization of propargyl alcohols and amides gave oxazoles. Herein, we report the synthesis and structural elucidation of 1 and its nethyl analog, 25methoxy1 benzofuran 3yln. Functional uses natural substances and extractives. Coumarone also benzofuran, a colorless liquid with a characteristic odor. Benzofuran derivatives possess several biological properties such as antiinflammatory, antimicrobial, antifungal, antihyperglycemic, analgesic, antiparasitic, and antitumor activities.
Benzofuran as a promising scaffold for the synthesis of. Benzofuran compounds are often analogues of mdxx and tryptamine compounds where a benzofuran ring has replaced the benzodioxole ring structure or indole ring respectively. It is the parent of many related compounds with more complex structures. Purchase transition metalcatalyzed benzofuran synthesis 1st edition. Files are available under licenses specified on their description page. With this method, a large number of hydroxylated benzofuran derivatives with different substitution. Benzofuran itself is a colorless liquid obtained from coal tar. Synthesis 7methoxy2methyl1 benzofuran 5carbaldehyde the usual method for the synthesis of 2ethylbenzofuran uses the salicylaldehyde as the starting material heating. These compounds showed optical and electrochemical properties that differ from their benzothiophene analog. Benzofuran is maillard produced present in roasted coffee aroma. All structured data from the file and property namespaces is available under the creative commons cc0 license.
Salicylaldehyde was taken then it is charged with chloroacetone 8. 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. Novel benzofuran derivatives bearing naryl piperazine moiety. Pdf synthesis of benzofuran derivatives and their evaluation of. Jan 21, 2020 with this method, a large number of hydroxylated benzofuran derivatives with different substitution. Benzofuran, solvent free condition, crossed aldol condensation. Methods for the synthesis of benzofuran derivatives. Synthesis and antimicrobial evaluation of new benzofuran. Benzofuran compounds are a class of compounds that are ubiquitous in nature. A diversity of synthetic routes can be applied to the synthesis of benzofurans. Synthesis of o iododiaryl ether was achieved in one pot through sequential iodination and oarylation of phenol under mild reaction conditions. Transition metalcatalyzed heterocycle synthesis series provides an overview of benzofuran, describing properties of these heterocycle compounds and the traditional synthetic procedures used for them. Total synthesis of the proposed structure of turkiyenine.
The part of the coal oil that contains 2,3benzofuran is made into a plastic called coumaroneindene resin. The obtained ethyl halobenzofuran2carboxylates 2a and 2b were next subjected to the reaction with 2amino2methylpropan1ol in the presence of ammonium chloride. The successful use of various iodinating agents, bases, additives etc. Palladiumcatalyzed carbonylative synthesis of benzofuran2. Synthesis of functionalized benzofurans from paraquinone. Syn thesis and antimicrobial activity of benzofuran 2yl 3phenyl3methylcyclobutyl ketoxime derivatives. This methodology has also been shown as the key step in a collective total synthesis of hydroxylated benzofuran. Herein, we report the synthesis and structural elucidation of 1 and its nethyl analog, 25methoxy1benzofuran3yln. Recent advancements 201417 in the benzofuran synthesis through iodocyclization have been summarized. Highly efficient enantioselective synthesis of bispiro. Total synthesis of natural products containing benzofuran rings.
Several natural products bearing benzofuran and its derivatives as a. Benzofuran definition of benzofuran by the free dictionary. Enantioselective synthesis of cyclopentabbenzofurans via. 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. A colorless liquid, c8h6o, found in coal tar and used to make thermoplastic resins for paints and varnishes. The detailed synthesis, spectroscopic data and antimicrobial activities of synthesized compounds were reported. Syntheses of benzofuran2carboxylic 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. Benzofuran is one of the most important fused heterocycles, containing a benzene ring fused to a furan ring.
It may also be formed during other uses of coal or oil. Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. An efficient method for the synthesis of dibenzofurans from oiododiaryl ethers is catalyzed by reusable pdc under ligandfree conditions. In scheme 1, iodination of phenol 1 with nai in the presence of naoh and naclo at low temperature 0 c gave the monoiodinephenol 2, which upon treatment with acetyl chloride produced intermediate 3. Synthesis of benzofuran 2carbohydrazide 4 31 the mixture of hydrazine hydrate 15 ml and ethyl benzofuran 2carboxylate 0. Media in category benzofuran the following 16 files are in this category, out of 16 total. For example, psoralen is a benzofuran derivative that occurs in several plants. Synthesis and pharmacological examination of benzofuran. 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. Benzofuran definition and meaning collins english dictionary. Using the conditions established for cicerfurane16, 6 was. Benzofurans heterocyclic building blocks sigmaaldrich.
The first step of the synthesis is a monobromination of tyrosol, which was performed as. Numerous approaches to these important compounds have been developed over the years but novel general procedures for their synthesis are still important. Benzofuran derviatives have shown biological activities ranging from antifungal and antimicrobial to antagonists for the h3 receptor and angiotensin ii. Then, the reaction mixture was stirred at room temperature to obtain benzofuran 2carbohydrazide as a. The mechanisms of the reactions and their use in the synthesis of biologically active substances are discussed. Nichols departments of medicinal chemistry and pharmacognosy and pharmacology and toxicology, school of pharmacy and. Using stoichiometric diacetoxyiodobenzene in acetonitrile, desired products can be isolated in good. The book then explores catalyzed procedures for benzofuran synthesis in greater detail and depth than is currently. Toxicological profile for 2,3benzofuran supplements the profile that was released in 1992. Benzofuran article about benzofuran by the free dictionary.
The characterization of 25methoxy1benzofuran3yl n,n. Transition metalcatalyzed benzofuran synthesis 1st edition. A versatile new synthesis of these compounds was reported starting with an acidcatalyzed cyclocondensation of phenols with glyoxylic acid to give the 3hydroxy3h benzofuran 2ones. Derivatives from tyrosol simple and efficient synthesis of. A palladiumcatalyzed carbonylative intramolecular synthesis of benzofuran23hones from 2hydroxybenzyl alcohols has been developed. The characterization of 62aminopropylbenzofuran and. However, ketones are rarely used in this reaction because of their low nucleophilicities. Synthesis and antimicrobial activity of some novel derivatives of benzofuran, part 1.
A convenient metalfree cyclization of orthohydroxystilbenes into 2arylbenzofurans and 2arylnaphthofurans is mediated by hypervalent iodine reagents. Then, the key benzofuran piperazine intermediate 4 was prepared by substitution with piperazine from compound 3 in the presence of k 2co 3 at 110 c in dmf. Benzofuran derivatives can be synthesized through the sequential michael addition and cyclization of 1,3. Palladiumcatalyzed carbonylative synthesis of benzofuran. Onepot synthesis protocol for highly functionalized. Journal of chemical and pharmaceutical research, 2012, 4. Benzofuran synthesis through iodocyclization reactions. Coupling of 3 with 1ethynyl4methoxybenzene, using the sonogashira protocol pdpph 3 2 cl. A diversity of synthetic routes can be applied to the synthesis of. 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. Toxicological profile for 2,3 benzofuran supplements the profile that was released in 1992. Cd 1 mmolwas dissolved in water 15 ml by warming up to 60 0 cuntil a clear solution was formed and then the sylicylaldehyde1 mmol dissolved in acetone 1 ml was added slowlywith.
Onestep regioselective synthesis of benzofurans from phenols and. His research is focused on heterocyclic chemistry, catalysis, organic. The substituted benzofurans are a class of chemical compounds based on the heterocyclyc and polycyclic compound benzofuran. Results and discussion the first set of experiments was directed towards the onepot protectioncouplingcyclization of bromohydroquinone 6, figure 3. Such as for the transformation of tyrosol into hydroxytyrosol, the aim of this work is to valorize an industrial waste. Pdf on dec 29, 2017, saurabh mehta and others published benzofuran synthesis through iodocyclization reactions. Natural source, bioactivity and synthesis of benzofuran derivatives.
Using stoichiometric diacetoxyiodobenzene in acetonitrile, desired products can be isolated in good yields. Expedited synthesis of benzofuran2carboxylic acids via. Syn thesis and antimicrobial activity of benzofuran2yl 3phenyl3methylcyclobutyl ketoxime derivatives. General procedure for synthesis of benzofuran2carboxylic acid 2hydroxy1,1dimethylethylamides 3a, 3b a mixture of benzofuran2carboxylic acid ethyl esters 2a or 2b 0. Highly efficient enantioselective synthesis of bispirobenzofuran oxindole pyrrolidines through organocatalytic cycloaddition boyu li, a fengyun gao, a xing feng, a mengmeng sun, a yifei guo, a dongwa wen, a yabo deng, a jinqi huang, b kairong wang a and wenjin yan a. 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 mechanisms of the reactions and their use in t. This onepot phospha1,6addition o acylationwittig reaction is also demonstrated under catalytic conditions with similar efficacy. Benzofuran derivatives, especially naphthofurans, constitute a valuable class of. Benzofuran is a fundamental structural unit in a variety of biologically active natural products as well as synthetic materials. Onestep regioselective synthesis of benzofurans from phenols. Jun 27, 2012 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 of new benzofuran2carboxylic acid derivatives. Benzofuran is the parent of many related compounds with more complex structures. A new approach to the synthesis of indoleand benzofuran. Use of the information, documents and data from the echa website is subject to the terms and conditions of this legal notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the echa website may be reproduced, distributed andor used, totally or in part, for noncommercial purposes provided. Onepot synthesis of novel symmetric 1,5dibenzofuran2. Quality supplier of research chemicals and biochemicals including inhibitors, building blocks, gmp products, impurities and metabolites, apis for veterinary, natural compounds, adcs, stem cell molecule and chiral compounds. Treating these compounds with aromatic or heteroaromatic hydrocarbons under friedelcrafts conditions yielded the corresponding 3aryl derivatives. From the tetracyclic systems with angular structure it is possible to. Synthetic utility of this process is shown in short synthesis of various natural products such as stemofuran a and eupomatenoid. Journal of chemical and pharmaceutical research, 2017, 95. Its derivatives are the scaffold of many natural products and several complex structures. A new method is described for the synthesis of the 1hbenzobfuroindole heterocyclic systems from the corresponding isomeric amino acids with amino groups at positions 2 and 3. With the desired intermediate 4 in hand, we began the synthesis of amines by treatment of compound 4 with several commercially available rx.
1402 1378 1253 108 272 1071 399 663 1376 1068 30 1235 1406 48 1221 464 1358 712 325 285 909 1192 1098 1312 225 1092 137 1003 871 1418 260 325 292 104 1424 1315 295 410 578 388