The book then explores catalyzed procedures for benzofuran synthesis in greater detail and depth than is currently. Total synthesis of natural products containing benzofuran rings. A diversity of synthetic routes can be applied to the synthesis of. From the tetracyclic systems with angular structure it is possible to. Additionally, data is presented for 42aminopropyl benzofuran 1, 52aminopropyl benzofuran 2, and 72aminopropyl benzofuran 4 to assist forensic chemists who may encounter these substances in casework.
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. Using the conditions established for cicerfurane16, 6 was. A new approach to the synthesis of indoleand benzofuran. 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. With the desired intermediate 4 in hand, we began the synthesis of amines by treatment of compound 4 with several commercially available rx.
The successful use of various iodinating agents, bases, additives etc. In this procedure, formic acid was utilized as the co source, and various benzofuran23hone derivatives were obtained in moderate to good yields. A synthetic route to novel benzofuran fused phosphole derivatives 35 is described. Benzofuran derivatives, especially naphthofurans, constitute a valuable class of. Numerous approaches to these important compounds have been developed over the years but novel general procedures for their synthesis are still important. Onestep regioselective synthesis of benzofurans from phenols and.
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. Benzofuran derivatives possess several biological properties such as antiinflammatory, antimicrobial, antifungal, antihyperglycemic, analgesic, antiparasitic, and antitumor activities. Files are available under licenses specified on their description page. Pdf benzofuran synthesis through iodocyclization reactions. Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. 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. An efficient method for the synthesis of dibenzofurans from oiododiaryl ethers is catalyzed by reusable pdc under ligandfree conditions. Synthesis and antimicrobial activity of some novel derivatives of benzofuran, part 1. Synthesis of o iododiaryl ether was achieved in one pot through sequential iodination and oarylation of phenol under mild reaction conditions. In this procedure, formic acid was utilized as the co source, and various benzofuran 23hone derivatives were obtained in moderate to good yields. The obtained ethyl halobenzofuran2carboxylates 2a and 2b were next subjected to the reaction with 2amino2methylpropan1ol in the presence of ammonium chloride. Using stoichiometric diacetoxyiodobenzene in acetonitrile, desired products can be isolated in good yields.
Enantioselective synthesis of cyclopentabbenzofurans via. Benzofuran as a promising scaffold for the synthesis of. Most of the benzofurans are research chemicals, most commonly stimulants and entactogens, and are fairly new. Pdf 2acetyl benzofuran 1 was synthesized by refluxing salicylaldehyde and dry chloroacetone in presence of potassium carbonate. Onepot synthesis of novel symmetric 1,5dibenzofuran2. Then, the reaction mixture was stirred at room temperature to obtain benzofuran 2carbohydrazide as a. Synthesis of oheterocycles benzofused oheterocycles synthesis of benzofurans. The part of the coal oil that contains 2,3benzofuran is made into a plastic called coumaroneindene resin. All structured data from the file and property namespaces is available under the creative commons cc0 license.
Then, the reaction mixture was stirred at room temperature to obtain benzofuran2carbohydrazide as a. Benzofuran derivatives can be synthesized through the sequential michael addition and cyclization of 1,3. Synthesis of functionalized benzofurans from paraquinone. Purchase transition metalcatalyzed benzofuran synthesis 1st edition. Benzofuran definition of benzofuran by the free dictionary. 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. Herein, we report the synthesis and structural elucidation of 1 and its nethyl analog, 25methoxy1benzofuran3yln. Benzofuran article about benzofuran by the free dictionary. Herein, we report the synthesis and structural elucidation of 1 and its nethyl analog, 25methoxy1 benzofuran 3yln. 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. Herein, we report a mild and broadly applicable method for the construction of complex benzofurylethylamine derivatives through a unique radical cyclization cascade. Ma and yuan recently disclosed a concise onepot synthesis of benzofuran derivatives using a benzyne precursor and a palladium0 source. 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. His research is focused on heterocyclic chemistry, catalysis, organic.
Synthesis 7methoxy2methyl1 benzofuran 5carbaldehyde the usual method for the synthesis of 2ethylbenzofuran uses the salicylaldehyde as the starting material heating. For example, psoralen is a benzofuran derivative that occurs in several plants. A colorless liquid, c8h6o, found in coal tar and used to make thermoplastic resins for paints and varnishes. Catalyzed skeletal rearrangement of spirotricyclic. Benzofuran coumarone, a heterocyclic compound consisting of fused benzene and furan rings, has been identified as a privileged structure in medicinal chemistry. Palladiumcatalyzed carbonylative synthesis of benzofuran. Benzofuran derviatives have shown biological activities ranging from antifungal and antimicrobial to antagonists for the h3 receptor and angiotensin ii. Benzofuran is a fundamental structural unit in a variety of biologically active natural products as well as synthetic materials. Pdf on dec 29, 2017, saurabh mehta and others published benzofuran synthesis through iodocyclization reactions. Institute of biology and molecular patologies ibpm, department of chemistry, sapienza university of rome, rome, italy. Synthesis and antimicrobial activity of furochromone, benzofuran.
Novel benzofuran derivatives bearing naryl piperazine moiety. Salicylaldehyde was taken then it is charged with chloroacetone 8. Jan 21, 2020 with this method, a large number of hydroxylated benzofuran derivatives with different substitution. Transition metalcatalyzed benzofuran synthesis 1st edition. Functional uses natural substances and extractives.
A palladiumcatalyzed carbonylative intramolecular synthesis of benzofuran 23hones from 2hydroxybenzyl alcohols has been developed. Using stoichiometric diacetoxyiodobenzene in acetonitrile, desired products can be isolated in good. Synthesis of benzofuran 2carbohydrazide 4 31 the mixture of hydrazine hydrate 15 ml and ethyl benzofuran 2carboxylate 0. Palladiumcatalyzed carbonylative synthesis of benzofuran2. Pdf synthesis of benzofuran derivatives and their evaluation of. Synthesis of new benzofuran2carboxylic acid derivatives.
Benzofurans are chemical compounds which contain a benzofuran ring in their structure. Several natural products bearing benzofuran and its derivatives as a. The mechanisms of the reactions and their use in the synthesis of biologically active substances are discussed. Transition metalcatalyzed heterocycle synthesis series provides an overview of benzofuran, describing properties of these heterocycle compounds and the traditional synthetic procedures used for them. 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. A synthetic route to novel benzofuranfused phosphole derivatives 35 is described. Benzofuran itself is a colorless liquid obtained from coal tar. However, ketones are rarely used in this reaction because of their low nucleophilicities. Media in category benzofuran the following 16 files are in this category, out of 16 total.
The cyclization of propargyl alcohols and amides gave oxazoles. Coupling of 3 with 1ethynyl4methoxybenzene, using the sonogashira protocol pdpph 3 2 cl. 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. 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. 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 and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4 methy1enedioxyamphetamine aaron p. Benzofuran is maillard produced present in roasted coffee aroma. Benzofuran synthesis through iodocyclization reactions. Syn thesis and antimicrobial activity of benzofuran 2yl 3phenyl3methylcyclobutyl ketoxime derivatives.
Synthesis and biological activities of some benzofuran. The first step of the synthesis is a monobromination of tyrosol, which was performed as. A palladiumcatalyzed carbonylative intramolecular synthesis of benzofuran23hones from 2hydroxybenzyl alcohols has been developed. 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 compounds are often analogues of mdxx and tryptamine compounds where a benzofuran ring has replaced the benzodioxole ring structure or indole ring respectively. Coumarone also benzofuran, a colorless liquid with a characteristic odor.
Methods for the synthesis of benzofuran derivatives. 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. 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. Benzofurans heterocyclic building blocks sigmaaldrich. Derivatives from tyrosol simple and efficient synthesis of. Preliminary results show that 4 can be used as an emitter in oleds, illustrating the potential of these new compounds for optoelectronic applications. Synthesis and pharmacological examination of benzofuran. 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. Synthesis of benzofuran derivatives through cascade.
A diversity of synthetic routes can be applied to the synthesis of benzofurans. This onepot phospha1,6addition o acylationwittig reaction is also demonstrated under catalytic conditions with similar efficacy. Onepot synthesis protocol for highly functionalized. 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. Treating these compounds with aromatic or heteroaromatic hydrocarbons under friedelcrafts conditions yielded the corresponding 3aryl derivatives. Its derivatives are the scaffold of many natural products and several complex structures. Highly efficient enantioselective synthesis of bispiro. Syn thesis and antimicrobial activity of benzofuran2yl 3phenyl3methylcyclobutyl ketoxime derivatives. Synthesis of benzofuran2carbohydrazide 4 31 the mixture of hydrazine hydrate 15 ml and ethyl benzofuran2carboxylate 0. Recent advancements 201417 in the benzofuran synthesis through iodocyclization have been summarized. Toxicological profile for 2,3benzofuran supplements the profile that was released in 1992.
Synthesis and antimicrobial evaluation of new benzofuran. The characterization of 25methoxy1benzofuran3yl n,n. Synthesis of 62aminopropylbenzofuran 3 and 42aminopropylbenzofuran 1 in accordance with journal policy, exact experimental details are not provided, but are outlined in figure 2. Synthetic utility of this process is shown in short synthesis of various natural products such as stemofuran a and eupomatenoid. Total synthesis of the proposed structure of turkiyenine. 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. Among 31tested compounds, some of them showed good activity selective. The substituted benzofurans are a class of chemical compounds based on the heterocyclyc and polycyclic compound benzofuran. With this method, a large number of hydroxylated benzofuran derivatives with different substitution.
This methodology has also been shown as the key step in a collective total synthesis of hydroxylated benzofuran. A convenient metalfree cyclization of orthohydroxystilbenes into 2arylbenzofurans and 2arylnaphthofurans is mediated by hypervalent iodine reagents. General procedure for synthesis of benzofuran2carboxylic acid 2hydroxy1,1dimethylethylamides 3a, 3b a mixture of benzofuran2carboxylic acid ethyl esters 2a or 2b 0. Onestep regioselective synthesis of benzofurans from phenols. Benzofuran is the parent of many related compounds with more complex structures.
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. It is the parent of many related compounds with more complex structures. Toxicological profile for 2,3 benzofuran supplements the profile that was released in 1992. 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. Nichols departments of medicinal chemistry and pharmacognosy and pharmacology and toxicology, school of pharmacy and.
Benzofuran definition and meaning collins english dictionary. Synthesis 7methoxy2methyl1benzofuran5carbaldehyde the usual method for the synthesis of 2ethylbenzofuran uses the salicylaldehyde as the starting material heating. Journal of chemical and pharmaceutical research, 2017, 95. Journal of chemical and pharmaceutical research, 2012, 4. 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, solvent free condition, crossed aldol condensation. It may also be formed during other uses of coal or oil. These compounds showed optical and electrochemical properties that differ from their benzothiophene analog. The characterization of 62aminopropylbenzofuran and. The mechanisms of the reactions and their use in t. Benzofuran is one of the most important fused heterocycles, containing a benzene ring fused to a furan ring. The detailed synthesis, spectroscopic data and antimicrobial activities of synthesized compounds were reported. Expedited synthesis of benzofuran2carboxylic acids via. Natural source, bioactivity and synthesis of benzofuran derivatives.
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