Expedited synthesis of benzofuran2carboxylic acids via. An international journal for rapid communication of synthetic organic chemistry. Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. 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. This method provides an efficient and alternative approach to benzofurans which are very useful heterocyclic compounds with. The committee concluded that the procedure could not be applied to this group because of unresolved toxicological concerns.
Onepot synthesis of 2,3disubstituted benzofurans from 2. Abstractthe title compound, c19h28o5si, was obtained in the reaction. Design, synthesis and evaluation of benzofuran acetamide scaffold as potential anticonvulsant agent ashok k. Onepot synthesis protocol for highly functionalized benzofuran. Pdf benzofuran synthesis through iodocyclization reactions. Synthesis of polyfluoroarenesubstituted benzofuran. A cooperative pdcucatalyzed dual ch bond activation of electrondeficient polyfluoroarenes with aryl halides is developed.
Ultrasound promoted green synthesis of benzofuran substituted. Nichols departments of medicinal chemistry and pharmacognosy and pharmacology and toxicology, school of pharmacy and. These compounds showed optical and electrochemical properties that differ from their benzothiophene analog. Files are available under licenses specified on their description page. 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. Due to the presence of benzofuran moiety, they have a great potential for biological activities and pharmaceutical utilities 35. Gouda 2014 reactivity of benzofuran derivatives, synthetic communications. Synthesis of 5benzofuran2yl24 chlorophenylthiazolo3,2b 1,2,4triazoles ivaivh. The cyclization of propargyl alcohols and amides gave oxazoles. Pdf 2acetyl benzofuran 1 was synthesized by refluxing salicylaldehyde and dry chloroacetone in presence of. 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. Article pdf available in ejournal of chemistry 72 april 2010 with 592 reads. Hence, different benzofurans having 4thiazolidinones have been synthesized for the purpose.
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. Benzofuran is the parent of many related compounds with more complex structures. Chasing the elusive benzofuran impurity of the thr. Highthroughput screening, discovery, and optimization to develop a benzofuran class of hepatitis c virus inhibitors. Compound data for new compounds 3aa, 4aa, 3ba, 4ba, 3cb, 3db, 3fa, 4fa, 3ac and 4ac including ortep drawing. A crystalline antioxidant extracted from yeast was shown to protect in vitro the erythrocytes of vitamin e deficient rats from hemolysis.
Benzofuran derivatives from alkynylsubstituted benzynes and. Using the conditions established for cicerfurane16, 6 was. Onestep regioselective synthesis of benzofurans from phenols and. Oct 04, 2010 read synthesis of benzofuran, benzothiophene, and benzothiazole. This article is from acta crystallographica section e. Design, synthesis and evaluation of benzofuranacetamide scaffold as potential anticonvulsant agent. Transitionmetalfree synthesis of c3arylated benzofurans. A new approach to the synthesis of indoleand benzofuran.
Cano, am1 theoretical study, synthesis and biological evaluation of some benzofuran analogues. Application of the benzofuran ring system in drug synthesis. 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. A convenient metalfree cyclization of orthohydroxystilbenes into 2arylbenzofurans and 2arylnaphthofurans is mediated by hypervalent iodine reagents. From the tetracyclic systems with angular structure it is possible to. Synthesis of benzofuran, benzothiophene, and benzothiazole. Synthesis of benzofuran derivatives via different methods. 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. 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. Many methodologies for the synthesis of benzofuran 2carboxylic acid skeleton were developed and most of them are based on the reaction of. Synthesis of elaborate benzofuran2carboxamide derivatives.
Benzofuran itself is a colorless liquid obtained from coal tar. Synthesis of benzofuran analogs of fenamates as non steroidal antiinflammatory agents, indian journal of chemistry, vol. Onepot synthesis protocol for highly functionalized benzofuran scaffold. Benzofuran derviatives have shown biological activities ranging from antifungal and antimicrobial to antagonists for the h3 receptor and angiotensin ii. Results and discussion the first set of experiments was directed towards the onepot protectioncouplingcyclization of bromohydroquinone 6, figure 3. Lewis acid mediated cycloaddition of benzoquinones with stilbene oxides. Pdf synthesis of benzofuran derivatives and their evaluation of. Our team of scientists has experience in all areas of research including life science, material science, chemical synthesis, chromatography, analytical and many others. The mechanisms of the reactions and their use in the synthesis of biologically active substances are discussed.
Synthesis of oheterocycles benzofused oheterocycles synthesis of benzofurans. Unlimited viewing of the articlechapter pdf and any associated supplements and figures. A synthetic route to novel benzofuranfused phosphole derivatives 35 is described. Postdoc journal journal of postdoctoral research vol. Synthesis of elaborate benzofuran 2carboxamide derivatives through a combination of 8aminoquinoline directed ch arylation and transamidation chemistry. The book then explores catalyzed procedures for benzofuran synthesis in greater detail and depth. Recent advancements 201417 in the benzofuran synthesis through iodocyclization have been summarized. Benzofuran is a hetrocylic compound consisting of fused benzene and a furan. For example, psoralen is a benzofuran derivative that occurs in several plants. Read online synthesis and evaluation of 41 benzofuran2 yl1,3. 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 as a promising scaffold for the synthesis of.
Understanding the mechanism of its formation has enabled isotope d labeling. Benzofuran synthesis through iodocyclization r eactions. Onepot synthesis protocol for highly functionalized. 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. All books are in clear copy here, and all files are secure so dont worry about it. The easily accessible benzofuran skeleton has been used as a platform for building two synthetic receptors able to associate with carboxylic acids and dinitrobenzoyl. Microwaveassisted parallel synthesis of benzofuran2carboxamide derivatives. 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. 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. Benzofurans are chemical compounds which contain a benzofuran ring in their structure. Such as for the transformation of tyrosol into hydroxytyrosol, the aim of this work is to valorize an industrial waste.
A colorless liquid, c8h6o, found in coal tar and used to make thermoplastic resins for paints and varnishes. Many methodologies for the synthesis of benzofuran2carboxylic acid skeleton were developed and most of them are based on the. H arylation and transamidation chemistry, and which enables access to a wide range of elaborate benzofuran 2carboxamides. 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. Design, synthesis and evaluation of benzofuranacetamide. 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. Benzofurans, sonogashira coupling, natural product, synthesis introduction. 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.
A protecting groupfree divergent synthesis of natural. 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. This protocol provides a unique and strategically distinct access to a variety of polyfluoroarenesubstituted benzofuran derivatives. Recent advances article pdf available december 2017 with 411 reads. A diversity of synthetic routes can be applied to the synthesis of benzofurans. Various natural and synthetic benzofuran derivatives are found to possess diverse applications in the field of medicine. We have synthesized and established the structure of a longsuspected, but hitherto unknown, benzofuran side product ebi formed during the synthesis of nh3. Synthesis of benzofuran derivatives and their evaluation of. Breaking the aromatic systems of electronrich arenes or heteroarenes provides threedimensional chemicals of high added value 1,2,3,4,5,6,7. We further developed a highly efficient method for. Read online synthesis and evaluation of 41 benzofuran 2 yl1,3. 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. The structure of this compound was determined as benzofuran derivative.
The successful use of various iodinating agents, bases, additives etc. Download acrobat pdf file 243kb supplementary data. Jun 27, 2012 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. We have also reported benzofuran synthesis from readily available 2chlorophenols and terminal alkynes using the pd. Derivatives from tyrosol simple and efficient synthesis of. The synthesis and spectral properties of benzofuran. Using stoichiometric diacetoxyiodobenzene in acetonitrile, desired products can be isolated in good yields. Although several methods have been reported to synthesis benzofuran derivatives involving a transition metal catalyzed reaction, 1 most of them are achieved by the reaction of prefunctionalized substrates,2, 3, 4 while there are only limited examples of the construction of benzofuran derivatives by intermolecular coupling using simple phenols. H arylation reactions, pd catalysis was used to install a wide range of aryl and heteroaryl substituents at the c3 position of the.
Transition metalcatalyzed heterocycle synthesis series provides an overview of benzofuran, describing properties of these heterocycle compounds and the traditional synthetic procedures used for them. Its derivatives are the scaffold of many natural products and several complex structures. 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. Benzofuran article about benzofuran by the free dictionary.
It may also be formed during other uses of coal or oil. In the spectrum, the molecular ion peak observed at mz 571. All structured data from the file and property namespaces is available under the creative commons cc0 license. The present protocol provides shorter ro synthetic methodology in obc. Ma and yuan recently disclosed a concise onepot synthesis of benzofuran derivatives using a benzyne precursor and a palladium0 source. A synthetic route to novel benzofuran fused phosphole derivatives 35 is described. Most of the benzofurans are research chemicals, most commonly stimulants and entactogens, and are fairly new. Electrooxidation enables highly regioselective dearomative.
This structure is also available as a 2d mol file or as a computed 3d sd file. 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. The first step of the synthesis is a monobromination of tyrosol, which was performed as. Herein we report the first onepot strategy for the efficient synthesis of 2bromo6hydroxybenzofurans. Nov 11, 2019 download synthesis and evaluation of 41 benzofuran2 yl1,3. Benzofuran compounds are often analogues of mdxx and tryptamine compounds where a benzofuran ring has replaced the benzodioxole ring structure or indole ring respectively. Methods for the synthesis of benzofuran derivatives. Synthesis of 2substituted benzofuran derivatives by the. Benzofuran definition of benzofuran by the free dictionary. From the tetracyclic systems with angular structure it is possible. Benzofuran as a promising scaffold for the synthesis of antimicrobial and antibreast cancer agents. 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. Synthesis of benzofuran 2carbaldehyde derivative 6.
The substituted benzofurans are a class of chemical compounds based on the heterocyclyc and polycyclic compound benzofuran. The structureactivity studies culminated in the design and synthesis of a 45compound library to comprehensively explore the antihcv activity. Siddiqui 1 department of chemistry 1, government institute of science, nagpur 440001, maharashtra, india. Benzofuran synthesis through iodocyclization reactions. Procter school of chemistry, university of manchester, oxford road, manchester m 9pl, u. This is a pdf file of an unedited manuscript that has been accepted for publication. Download fulltext pdf benzofuran synthesis through iodocyclization reactions. Download synthesis and evaluation of 41 benzofuran 2 yl1,3. Synthesis and pharmacological examination of benzofuran.
If you have problems viewing pdf files, download the latest. For more information, please view spec of benzofuran 6carboxylic acid 770955. 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. Highthroughput screening, discovery, and optimization to. The sonogashira5 endodig combination in benzofuran synthesis. Synthesis and biological activities of some benzofuran.
Benzofurans heterocyclic building blocks sigmaaldrich. Another two catalysts, pdnh34nay and pdcald were successfully used for the synthesis of benzofuran derivatives scheme 46 9. It is well known that vitamin e having chroman skeleton have a. Cascade claisen and meinwald rearrangement for onepot. Transition metalfree synthesis of c3arylated benzofurans from benzothiophenes and phenols kevin yang, alexander p. Benzofuran is one of the most important fused heterocycles, containing a benzene ring fused to a furan ring. Journal of chemical and pharmaceutical research, 2017, 95. This is a pdf file of an unedited manuscript that has been.
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