The key feature of the improved process is one pot high yielding deprotection of. The synthesis of these important molecules can be achieved by construction of one or both rings, or via direct functionalization of the benzothiophene core 9,10,11. Synthesis and structure elucidation of some novel thiophene and. Synthesis of 1benzothieno3,2b1benzothiophene derivatives via. Benzothiophene article about benzothiophene by the free. The format of this chapter makes it easy for the reader to understand the subject in a.
Synthesis of benzothiophene and indole derivatives through metalfree propargylallene rearrangement and allyl migration jinzhongyao, yajiexie, lianpengzhang, yujinli andhongweizhou full research paper open access address. These peptides exhibit important antimicrobial, antiviral, and anticancer activities. Synthesis of benzothiophene derivatives by pdcatalyzed or. Both aliphatic and aromatic carboxylic acids participated in trifluoroacetic anhydridephosphoric acid mediated cc bond forming reactions under solventfree conditions affording acyl. Recent advances in the synthesis of benzothiophenes. Synthesis of 1 benzothieno 3, 2b1 benzothiophene derivatives. Pdf benzothiophene derivatives were synthesized regioselectively using coupling reactions and electrophilic cyclization reactions. I, the holder of this work, release this work into the public domain. Pdf synthesis and biological evaluation of novel benzothiophene.
Different substitution patterns in these heterocycles provide new opportunities for. Benzothiophene and its derivatives have been reported to show activity in treating various medical conditions, such as hyperlipidemia, breast cancer, and uterus cancer charles et al. Simultaneous inhibition of 5loxcox may enhance antiinflammatory effects and reduce side effects. Solid phase synthesis of peptides provides the methods to prepare and investigate novel compounds for possible use as antibiotics. Differently substituted 2,5diarylthiazole can be obtained with the same catalyst system by switching the solvent and the. Synthesis and antimicrobial activity of benzothiophene. The preparation of some heteroaromatic and aromatic. Files available from the acs website may be downloaded for personal use only. In order to obtain the desired sulfone derivatives, the sulfide group underwent oxidation with mcpba to.
In addition to benzobthiophene, a second isomer is known. A novel approach for the stereoselective synthesis of benzothiophene derivatives with a fused dihydropyran moiety is demonstrated. Thiophene derivatives are a very important class of compounds with different uses, including industrial and medicinal chemistry 14. Synthesis, matrix isolation, spectroscopy, mechanistic studies, and computational chemistry mcmahon research group computational studies have been carried out on both the 2 and 3substituted benzothiophene carbenes and their possible rearrangement products at. The method makes it possible to produce the tetracyclic systems with both angular and linear structure. Benzothiophene finds use in research as a starting material for the synthesis of larger, usually. A welldefined series of long and soluble isoindigo thienoacene oligomers have been synthesized from a novel electron deficient building block. Journal of materials chemistry c synthesis of 1benzothieno3,2 b 1benzothiophene pendant and norbornene random copolymers via ring opening metathesis craig m. A palladiumcatalyzed ch arylation of electronenriched heteroarenes with aryl bromides and aryl chlorides proceeds in the presence of liotbu as a base. Hydrodesulfurization of thiophene, benzothiophene, dibenzothiophene, and related compounds catalyzed by sulfided coomo3gammaal2o3.
To address this, we have attempted heteroatom oxygen functionalization of btbt by a concise and easily scalable synthesis. Synthesis of benzothiophene and indole derivatives through metal. Preparation of 3amino6fluorobenzothiophene2carbohydrazide 2 to a stirred solution of methyl3amino6fluorobenzothiophene2carboxylate 1 2. Cyclization of 4ae with thioglycolic or thiolactic acids brought about the target spiro compounds 5ae and 6ae respectively. To address this, we have attempted heteroatom oxygen functionalization of btbt by a concise and easily scalable. Notably, while the use of various arenesheteroarenes has been explored in the previous study, 2530 the use of benzothiophene has not been examined so far. Benzothiophene is an aromatic organic compound with a molecular formula c8h 6s and an.
A new synthetic method for 1 benzothieno 3,2b1 benzothiophene derivatives btbts was developed. Synthesis and antimicrobial activities of benzothiophene. However, 1h, c nmr spectra show that the formylation of 6c with secbuli and dmf afforded an inseparable mixture due to their close r f values of benzothiophene3carboxaldehyde 7c and benzothiophene2carboxaldehyde 2b. College of biological, chemical sciences and engineering, jiaxing university, jiaxing 314001, p.
Structure, properties, spectra, suppliers and links for. Benzothiophenes were also synthesized selectively by simply increasing the amount of thionyl chloride. It is a colourless solid that is chemically somewhat similar to anthracene. Keywords benzothiophenes, fluorinated drugs, antitrypanosomal activity. Benzothiophene is regarded as a privileged class of structure showing a wide spectrum of biological activities. Synthesis and properties of isoindigo and benzo1,2b.
Benzothiophene is an aromatic organic compound with a molecular formula c 8 h 6 s and an odor similar to naphthalene mothballs. In particular, 12mercaptophenyl2yn1ols 2, bearing a ch2r substituent on the triple bond r alkyl, aryl. Synthesis of 1 benzothieno 3,2b1 benzothiophene derivatives via successive iodocyclizationphotocyclization of alkynes the journal of organic chemistry. A simple and singlestep synthesis of 2 and 3acyl substituted benzothiophenes has been described via environmentally benign acylation of benzothiophene with in situ generated acyl trifluoroacetates. We demonstrated that the 3substituted benzothiophene1,1dioxide class of compounds are effective inhibitors of mycobacterium tuberculosis growth under aerobic conditions. Hence, synthesis of novel dual inhibitors of 5loxcox is an important strategy for treatment of inflammation. Attempting to produce cyclized systems with potential antiproliferative activity, a series of novel thiophene and benzothiophene derivatives were designed and synthesized. Diisobutylaluminum hydride promoted selectivityswitchable. We examined substitution at the c3 position of the benzothiophene1,1. Benzothiophene finds use in research as a starting material. Dibenzothiophene dbt is the organosulfur compound consisting of two benzene rings fused to a central thiophene ring. Synthesis of benzothiophene carboxamide derivatives and. What are the possible starting materials for the synthesis. Preparation of the benzothiophene 3a under sunlight irradiation.
Synthesis of sheterocycles benzofused sheterocycles synthesis of benzothiophenes. Synthesis and antitubercular activity of 3substituted benzothiophene1,1dioxides we demonstrated that the 3substituted benzothiophene1,1dioxide class of compounds are efective inhibitors of mycobacterium tuberculosis growth under aerobic conditions. We developed an efficient and direct method for synthesis of benzothiophene oxides from 1bromo22trimethylsilylethynylbenzenes and thionyl chloride as an easily accessible source of the sulfinyl group. Benzothiophenes, an important class of heterocycles, are privileged structures, used as starting materials for the synthesis of bioactive structures, and are present in pharmaceuticals. A highly efficient synthesis of benzothiophenes from easily available o halovinylbenzenes and potassium sulfide tolerates a wide range of functionalities and provides various 2substituted benzo b thiophenes in high yields in the absence of a transitionmetal catalyst. Compound s2 was synthesized according to a known procedure. We report the subsequent functionalization of this compound into iodine, boronic ester and silane derivatives, which are useful intermediates for various applications. We describe a simple three step synthesis of naphtho2,1. Full paper results and discussion previously, we reported on synthetic methodologies for the preparation of thieno2,3dpyrimidinebased bisphosphonate10 and monosphosphonate thpmps11 libraries of com pounds with the ability to inhibit isoprenoid biosynthesis. Synthesis and anticonvulsant activity of new 3aryl7bromospiro 1benzothiophene3,21,3thiazolidine. The target compounds were designed to hybridize benzothiophene scaffold or its bioisostere benzofuran with various antiinflammatory pharmacophore. Design, synthesis and antitrypanosomal activities of 2,6. A new method is described for the synthesis of the heterocyclic systems of benzobthiophenoindoles from the respective isomeric amino acids with amino groups at positions 2 and 3. It is a member of dibenzothiophenes and a mancude organic heterotricyclic parent.
A convenient synthesis of benzothiophene derivatives. Synthesis of benzothiophene and indole derivatives through metalfree propargylallene rearrangement and allyl migration. Jinzhongyao, yajiexie, lianpengzhang, yujinli andhongweizhou. Regioselective synthesis of c3 alkylated and arylated. Derivatives of benzobthiophenes are useful precursors for the synthesis of thioindigo and azo disperse dyes. Novel benzothiophene 1,1dioxide deoxygenation path for.
Design, synthesis, chemical stability, packing, cyclic. These methods achieved efficient syntheses of various benzothiophene oxides and. The present work details the journey towards development of a simple, cost effective, environmentally friendly synthesis of raloxifene hydrochloride 1. Gadada naganagowda, patchanita thamyongkit, amorn petsom research center for bioorganic chemistry, department of chemistry, faculty of science, chulalongkorn university, bangkok 10330, thailand.
Hence versatile synthetic strategies are needed to discover the properties of this molecule. Synthesis of c2 substituted benzothiophenes via an. Synthesis unit 4 synthesis and reactions of isoquinolines unit 5 application of the isoquinoline ring system in drug synthesis module 2 benzofuran, benzothiophene and indoles unit 1 reactions of benzopyrrole indole unit 2 synthesis of benzopyrrole indole unit 3. On the other hand, other groups of compounds such as benzophenone, aminopyridine, and amisynthesis of benzothiophene carboxamide derivatives and. It occurs naturally as a constituent of petroleumrelated deposits such as lignite tar. In some countries this may not be legally possible. Subsequent alkylation with 1bromo5methylhexane in dmf62 led to 3b in 58% yield. The reaction of c4substitutedphenylnbenzoylnmethylglycines with benzobthiophene 1,1dioxide unexpectedly gave benzothiophenefused pyrrole derivatives in toluene under microwave irradiation via a cycloaddition and metalfree pummerertype sulfone deoxygenation path. For example, the preparation of c3borylated benzothiophene by bcl3induced borylative cyclization of arylalkynes was recently. Synthesis and antitubercular activity of 3substituted.
Aminocatalytic strategy for the synthesis of optically. The larock indole synthesis using orthohaloaniline derivatives is a. Its various derivatives are useful as pesticides, fungicides, and herbicides. In the past decade, a large number of naturally occuring thiazole and oxazolecontaining peptides have been isolated from microbial and marine origins. The presence of high amounts of sulfur in soils adjacent to the study area was reported by fernandez et al. A practical synthesis of benzothiophenes via visiblelightpromoted. Gurnos jones arkivoc 2000 iii 240251 issn 15517004 page 243 arkat usa, inc 3bromobenzothiophene 6c in 60% yield. Transitionmetalfree synthesis of c3arylated benzofurans. Pdf synthesis of benzothiophene and indole derivatives through. What links here related changes upload file special pages permanent link page. Synthesis of benzothiophene and indole derivatives through.
Synthesis and structure elucidation of some novel thiophene and benzothiophene derivatives as cytotoxic agents. Novel and convenient approaches to benzothiophene derivatives 3 and 5 have been developed, based on heterocyclization reactions of 12mercaptophenyl2yn1ols 2 or 4, respectively, readily available from alkynylation of 2mercaptobenzaldehydes or 12mercaptophenyl ketones 1. We examined substitution at the c3 position of the benzothiophene1,1dioxide series systematically to delineate structureactivity relationships influencing potency and cytotoxicity. Synthesis, properties, and structures of benzo1,2b. The present method consists of iodocyclization of 1,2bis2methylthiophenylethynes and photolysis of 3iodo2methylthiophenylbenzobthiophenes. Dibenzothiophene is a mancude organic heterotricyclic parent that consists of a thiophene ring flanked by two benzene rings orthofused across the 2,3 and 4,5positions. New benzothiophene derivatives as dual cox12 and 5lox. Synthesis and anticonvulsant activity of new 3aryl7. New method for the synthesis of indoleand benzothiophene. Download fulltext pdf download fulltext pdf synthesis and antimicrobial activities of benzothiophene derivatives article pdf available in journal of the chilean chemical society 571. Benzothiophenes heterocyclic building blocks sigmaaldrich.