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