Unlimited viewing of the articlechapter pdf and any associated supplements and figures. An international journal for rapid communication of synthetic organic chemistry. Results and discussion the first set of experiments was directed towards the onepot protectioncouplingcyclization of bromohydroquinone 6, figure 3. A new cascade approach has been developed for the onepot fourstep divergent synthesis of polysubstituted benzofurans and 2hchromenes, featuring a novel cascade aromatic claisen rearrangementmei. Benzofuran as a promising scaffold for the synthesis of antimicrobial and antibreast cancer agents. Benzofuran article about benzofuran by the free dictionary.
Breaking the aromatic systems of electronrich arenes or heteroarenes provides threedimensional chemicals of high added value 1,2,3,4,5,6,7. Highthroughput screening, discovery, and optimization to develop a benzofuran class of hepatitis c virus inhibitors. From the tetracyclic systems with angular structure it is possible to. The structureactivity studies culminated in the design and synthesis of a 45compound library to comprehensively explore the antihcv activity. We further developed a highly efficient method for. The synthesis of the benzofuran framework allows for functionalization with hydrogen bond.
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. Abstractthe title compound, c19h28o5si, was obtained in the reaction. This article is from acta crystallographica section e. The first step of the synthesis is a monobromination of tyrosol, which was performed as. A synthetic route to novel benzofuran fused phosphole derivatives 35 is described. A diversity of synthetic routes can be applied to the synthesis of benzofurans. The mechanisms of the reactions and their use in the synthesis of biologically active substances are discussed. 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. Cano, am1 theoretical study, synthesis and biological evaluation of some benzofuran analogues.
Download fulltext pdf benzofuran synthesis through iodocyclization reactions. Files are available under licenses specified on their description page. Compound data for new compounds 3aa, 4aa, 3ba, 4ba, 3cb, 3db, 3fa, 4fa, 3ac and 4ac including ortep drawing. Siddiqui 1 department of chemistry 1, government institute of science, nagpur 440001, maharashtra, india. Procter school of chemistry, university of manchester, oxford road, manchester m 9pl, u. Derivatives from tyrosol simple and efficient synthesis of. Synthesis of benzofuran analogs of fenamates as non steroidal antiinflammatory agents, indian journal of chemistry, vol. Download acrobat pdf file 243kb supplementary data. Expedited synthesis of benzofuran2carboxylic acids via.
Methods for the synthesis of benzofuran derivatives. The cyclization of propargyl alcohols and amides gave oxazoles. 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. Dronedarone multaq, a benzofuran derivative that is an analogue of amiodarone, is approved in the united states and the european union for a different population of patients with af, not those with permanent af, and the benefitrisk of multaq remains unchanged in its approved indication in nonpermanent af, the company said in a press release. The sonogashira5 endodig combination in benzofuran synthesis. The present protocol provides shorter ro synthetic methodology in obc. Postdoc journal journal of postdoctoral research vol. The substituted benzofurans are a class of chemical compounds based on the heterocyclyc and polycyclic compound benzofuran. Onepot synthesis of 2,3disubstituted benzofurans from 2. Our team of scientists has experience in all areas of research including life science, material science, chemical synthesis, chromatography, analytical and many others. For more information, please view spec of benzofuran 6carboxylic acid 770955.
Microwaveassisted parallel synthesis of benzofuran2carboxamide derivatives. A simple onepot procedure has been elaborated for the preparation of substituted benzofurans starting from halogenated phenols, and this method has been applied successfully to the total synthesis of dehydrotremetone, a natural product of white snakeroot. Pdf benzofuran synthesis through iodocyclization reactions. Jun 03, 20 read benzofuran synthesis via coppermediated oxidative annulation of phenols and unactivated internal alkynes, chemical science on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. Benzofuran compounds are often analogues of mdxx and tryptamine compounds where a benzofuran ring has replaced the benzodioxole ring structure or indole ring respectively. Pdf 2acetyl benzofuran 1 was synthesized by refluxing salicylaldehyde and dry chloroacetone in presence of. For example, psoralen is a benzofuran derivative that occurs in several plants. Many methodologies for the synthesis of benzofuran2carboxylic acid skeleton were developed and most of them are based on the. Ultrasound promoted green synthesis of benzofuran substituted. Transitionmetalfree synthesis of c3arylated benzofurans. 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. Transition metalcatalyzed benzofuran synthesis 1st edition. In cold condition, staudinger reaction was carried out for compound 2 with various acid chlorides in presence of triethylamine to synthesize 41 benzofuran 2yl. This method provides an efficient and alternative approach to benzofurans which are very useful heterocyclic compounds with.
We have synthesized and established the structure of a longsuspected, but hitherto unknown, benzofuran side product ebi formed during the synthesis of nh3. Nichols departments of medicinal chemistry and pharmacognosy and pharmacology and toxicology, school of pharmacy and. The synthesis and spectral properties of benzofuran. Synthesis of elaborate benzofuran2carboxamide derivatives. Highthroughput screening, discovery, and optimization to. Synthesis of oheterocycles benzofused oheterocycles synthesis of benzofurans. Based thioamides and their evaluation as k atp channel openers, chemmedchem on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. Benzofuran synthesis through iodocyclization r eactions. Benzofuran derivatives from alkynylsubstituted benzynes and. Synthesis of benzofuran derivatives via different methods.
Journal of chemical and pharmaceutical research, 2017, 95. Onepot synthesis protocol for highly functionalized benzofuran. Benzofurans are chemical compounds which contain a benzofuran ring in their structure. All structured data from the file and property namespaces is available under the creative commons cc0 license. From the tetracyclic systems with angular structure it is possible. Many methodologies for the synthesis of benzofuran 2carboxylic acid skeleton were developed and most of them are based on the reaction of. Benzofuran coumarone, a heterocyclic compound consisting of fused benzene and furan rings, has been identified as a privileged structure in medicinal chemistry. Onepot synthesis protocol for highly functionalized. Benzofuran itself is a colorless liquid obtained from coal tar. Pdf synthesis of benzofuran derivatives and their evaluation of. Onestep regioselective synthesis of benzofurans from phenols and.
This is a pdf file of an unedited manuscript that has been. Oct 04, 2010 read synthesis of benzofuran, benzothiophene, and benzothiazole. Benzofuran synthesis through iodocyclization reactions. It is well known that vitamin e having chroman skeleton have a. This is a pdf file of an unedited manuscript that has been accepted for publication.
Benzofurans heterocyclic building blocks sigmaaldrich. A convenient metalfree cyclization of orthohydroxystilbenes into 2arylbenzofurans and 2arylnaphthofurans is mediated by hypervalent iodine reagents. Nov 11, 2019 download synthesis and evaluation of 41 benzofuran2 yl1,3. If you have problems viewing pdf files, download the latest. Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4 methy1enedioxyamphetamine aaron p. The mgla mixed oxidesupported pd catalyst is air and moisture stable and highly efficient for the synthesis of benzofuran derivatives involving sonogashira reaction between ohalo phenol and terminal alkynes. Most of the benzofurans are research chemicals, most commonly stimulants and entactogens, and are fairly new. Transition metalcatalyzed heterocycle synthesis series provides an overview of benzofuran, describing properties of these heterocycle compounds and the traditional synthetic procedures used for them. Recent advances article pdf available december 2017 with 411 reads. Download synthesis and evaluation of 41 benzofuran 2 yl1,3. Chasing the elusive benzofuran impurity of the thr. Read online synthesis and evaluation of 41 benzofuran 2 yl1,3.
Synthesis of benzofuran 2carbaldehyde derivative 6. Benzofuran is the parent of many related compounds with more complex structures. Various natural and synthetic benzofuran derivatives are found to possess diverse applications in the field of medicine. Preliminary results show that 4 can be used as an emitter in oleds, illustrating the potential of these new compounds for optoelectronic applications.
Synthesis of new benzofuran2carboxylic acid derivatives. Benzofuran derviatives have shown biological activities ranging from antifungal and antimicrobial to antagonists for the h3 receptor and angiotensin ii. The easily accessible benzofuran skeleton has been used as a platform for building two synthetic receptors able to associate with carboxylic acids and dinitrobenzoyl. These compounds showed optical and electrochemical properties that differ from their benzothiophene analog. Article pdf available in ejournal of chemistry 72 april 2010 with 592 reads. Read online synthesis and evaluation of 41 benzofuran2 yl1,3. Hence, different benzofurans having 4thiazolidinones have been synthesized for the purpose. This structure is also available as a 2d mol file or as a computed 3d sd file. Design, synthesis and evaluation of benzofuranacetamide. Benzofuran is a hetrocylic compound consisting of fused benzene and a furan.
Electrooxidation enables highly regioselective dearomative. H arylation reactions, pd catalysis was used to install a wide range of aryl and heteroaryl substituents at the c3 position of the. Herein we report the first onepot strategy for the efficient synthesis of 2bromo6hydroxybenzofurans. Key laboratory of material chemistry for energy conversion and storage, ministry of education, school of chemistry and chemical engineering, huazhong university of science and technology, wuhan 430074, peoples republic of china. Cascade claisen and meinwald rearrangement for onepot. Ma and yuan recently disclosed a concise onepot synthesis of benzofuran derivatives using a benzyne precursor and a palladium0 source. Synthesis of 2substituted benzofuran derivatives by the. H arylation and transamidation chemistry, and which enables access to a wide range of elaborate benzofuran 2carboxamides. All books are in clear copy here, and all files are secure so dont worry about it. Recent advancements 201417 in the benzofuran synthesis through iodocyclization have been summarized. Design, synthesis and evaluation of benzofuran acetamide scaffold as potential anticonvulsant agent ashok k. Lewis acid mediated cycloaddition of benzoquinones with stilbene oxides.
Studies that could assist in the safety evaluation include investigations of the influence of the nature and position of furan ring substitutions on metabolism and covalent binding to macromolecules, demonstration of the ring opening and reactivity of the resulting products. Using the conditions established for cicerfurane16, 6 was. Synthesis of elaborate benzofuran 2carboxamide derivatives through a combination of 8aminoquinoline directed ch arylation and transamidation chemistry. The microwaveassisted perkin rearrangement reaction presented here provides a more efficient synthesis of benzofuran 2carboxylic acids from 3bromocoumarins with a reaction time of 5 minutes in comparison to the traditional method with a reaction time of approximately 3 hours. Benzofuran as a promising scaffold for the synthesis of. Such as for the transformation of tyrosol into hydroxytyrosol, the aim of this work is to valorize an industrial waste. Benzofurans, sonogashira coupling, natural product, synthesis introduction. A protecting groupfree divergent synthesis of natural. 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. Another two catalysts, pdnh34nay and pdcald were successfully used for the synthesis of benzofuran derivatives scheme 46 9. Onepot synthesis protocol for highly functionalized benzofuran scaffold.
A crystalline antioxidant extracted from yeast was shown to protect in vitro the erythrocytes of vitamin e deficient rats from hemolysis. It may also be formed during other uses of coal or oil. Synthesis of polyfluoroarenesubstituted benzofuran. Using stoichiometric diacetoxyiodobenzene in acetonitrile, desired products can be isolated in good yields. 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 committee concluded that the procedure could not be applied to this group because of unresolved toxicological concerns. Transition metalfree synthesis of c3arylated benzofurans from benzothiophenes and phenols kevin yang, alexander p. Understanding the mechanism of its formation has enabled isotope d labeling. We have also reported benzofuran synthesis from readily available 2chlorophenols and terminal alkynes using the pd. The successful use of various iodinating agents, bases, additives etc.
Design, synthesis and evaluation of benzofuranacetamide scaffold as potential anticonvulsant agent. A new approach to the synthesis of indoleand benzofuran. 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. Application of the benzofuran ring system in drug synthesis. A synthetic route to novel benzofuranfused phosphole derivatives 35 is described. Due to the presence of benzofuran moiety, they have a great potential for biological activities and pharmaceutical utilities 35. Synthesis and biological activities of some benzofuran. 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. Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. Gouda 2014 reactivity of benzofuran derivatives, synthetic communications. Synthesis of benzofuran, benzothiophene, and benzothiazole. A cooperative pdcucatalyzed dual ch bond activation of electrondeficient polyfluoroarenes with aryl halides is developed.
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