A new synthetic method for 1benzothieno3,2b1 benzothiophene derivatives btbts was developed. What are the possible starting materials for the synthesis. A highly efficient synthesis of benzothiophenes from easily available ohalovinylbenzenes and potassium sulfide tolerates a wide range of functionalities and provides various 2substituted benzo bthiophenes in high yields in the absence of a transitionmetal catalyst. Some authors have reported anaerobic desulfurization by sutfatereducing bacteria. 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. It occurs naturally as a constituent of petroleumrelated deposits such as lignite tar. In the present research manuscript, we described a series of new compounds containing coumarins, pyrimidines and pyrazole substituted benzothiophene derivatives 3af, 4, 5, and 7 have been synthesized from 2,4diflurobenzonitrile and methyl thioglycolate as starting material. Synthesis of c2 substituted benzothiophenes via an. Synthesis and evaluation of a series of benzothiophene acrylonitrile analogs as anticancer agents. 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.
Biodesulfurization of dibenzothiophene by a newly isolated. An interrupted pummerer reaction between benzothiophene s. Electronic transport of benzothiophenebased chiral. Synthesis of benzothiophene and indole derivatives through. Organic sulfur compound of fossil fuel are too resistant to be removed by the conventional desulfurization processes. It is also used in the manufacturing of dyes such as thioindigo. For further information contact manager repository services. Synthesis and antimicrobial activities of benzothiophene derivatives article pdf available in journal of the chilean chemical society 571. Benzofuran is the parent of many correlated compounds with more complex structures. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, and sertaconazole, and also btcp. Synthesis and antimicrobial activities of benzothiophene. A practical synthesis of benzothiophenes via visiblelightpromoted. A ftir study of the adsorption of indole, carbazole. Hydrophobic interactions improve selectivity to er.
Benzothiophenes, an important class of heterocycles, are privileged structures, used as starting materials for the synthesis of bioactive structures, and are. Benzothiophene is an aromatic organic compound with a molecular formula c8h 6s and an. Dibenzothiophene dbt is the organosulfur compound consisting of two benzene rings fused to a central thiophene ring. It is a colourless solid that is chemically somewhat similar to anthracene. Sulfur can be removed from benzothiophene bt by some bacteria without breaking carboncarbon bonds. Synthesis and reactions of benzofuran and benzothiophene, chemistry tutorial. These catalytic reactions are biphydrodesulfurizations bhds.
Us6048875a benzothiophene, benzofuran and indole compounds. Identification of benzothiophene carboxylate derivatives as novel bdk inhibitors. Synthesis and antimicrobial activity of benzothiophene. Benzothiophenes, an important class of heterocycles, are privileged structures, used as starting materials for the synthesis of bioactive structures, and are present in pharmaceuticals. Benzothiophene3carboxaldehyde, hive tryptamine chemistry. The synthesis of photochromic compounds containing combinations of benzothiophene and thiophene 70 04jppa97, 09jms100, indene 71 06tl1267, or benzofuran rings 72 and 73 06bcj1100, 08bcsj644 was documented scheme 22. Files are available under licenses specified on their description page. Synthesis of benzothiophene derivatives by pdcatalyzed or. Dibenzothiophene is listed in the worlds largest and most authoritative dictionary database of abbreviations and acronyms. Gadada naganagowda, patchanita thamyongkit, amorn petsom research center for bioorganic chemistry, department of chemistry, faculty of science, chulalongkorn university, bangkok 10330, thailand. Different substitution patterns in these heterocycles provide new. However, a clear mechanism for bt desulfurization and its genetic components have not been reported in literatures so far. This colourless solid is a component of the coal tar.
Us4380635a us06331,046 us33104681a us4380635a us 4380635 a us4380635 a us 4380635a us 33104681 a us33104681 a us 33104681a us 4380635 a us4380635 a us 4380635a authority us united states prior art keywords ml process ch product mixture prior art date 19810403 legal status the legal status is an assumption and is not a legal conclusion. It was designed to improve the bioavailability of raloxifene and provide sustained antiestrogenic blockade in the treatment of. Benzothiophenes heterocyclic building blocks sigmaaldrich. Supporting information supporting information file 1 experimental procedures and analytical data. This study aimed to investigate the best growth conditions of agrobacterium tumefaciens strain lsu20 on desulfurized of dibenzothiophene dbt compound in the ntetradecane as model of oil. Mild reaction conditions, a onepot procedure, and easily accessible starting materials make these protocols powerful tools for the synthesis of these compounds, which are often used in. New benzothiophene derivatives as dual cox12 and 5lox. Regioselective synthesis of c3 alkylated and arylated. Looking for online definition of dibenzothiophene or what dibenzothiophene stands for.
The experiments were performed with the medium two. Predicted data is generated using the us environmental protection agencys episuite. Phosphinate and phosphonate derivatives can serve as useful transition. Communications in tetrahedron letters are expected to represent brief summaries of preliminary work or initial results at the cutting edge of the field. Dibenzothiophene what does dibenzothiophene stand for. Figure 2 is a new benzothiophene analog that is structurally related to raloxifene.
Tetrahedron letters also publishes digests, commissioned. Aerobic oxidative desulfurization of benzothiophene, dibenzothiophene and 4,6dimethyldibenzothiophene using an andersontype catalyst c. Novel and convenient approaches to benzothiophene derivatives 3 and 5 have been developed, based on heterocyclization reactions of 12 mercaptophenyl 2yn1ols 2 or 4, respectively, readily available from alkynylation of 2mercaptobenzaldehydes or 12mercaptophenyl ketones 1. With 1,2bis2methylthiophenylethynes treated with i2phioac2 in ch2cl2 at room temperature, selective cyclization at sulfur took place to. Trakarnpruk petrochemistry and polymer science, faculty of science, chulalongkorn university, bangkok 10330, thailand oxidative desulfurization of model compounds benzothiophene, dibenzothiophene, 4,6dimethyldibenzo. The key feature of the improved process is one pot high yielding deprotection of sulfonyl group in water. This tricyclic heterocycle, and especially its alkyl substituted derivatives, occur widely in heavier fractions of petroleum. 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. Rapid publication of such research enables authors to transmit their new contributions quickly to a large, international audience. The subsequently generated benzothiophenium salts undergo a previously unexplored 1,2migration to access c2 functionalized benzothiophenes. In order to obtain the desired sulfone derivatives, the sulfide group. The birch reductions of benzothiophene and dibenzothiophene have been studied for a number of years. Two efficient synthetic protocols were developed for the synthesis of dibenzothiophene and 1,4dihydrodibenzothiophene using thioaurones and allylic phosphonium salt. Electronic transport of benzothiophenebased chiral molecular solenoids studied by theoretical simulations katsunori tagami, masaru tsukada, yasuo wada, tomokazu iwasaki, hiroyuki nishide waseda research institute for science and engineering.
Preparation of the benzothiophene 3a under sunlight irradiation. Oxidative desulfurization using polyoxometalates c. Synthesis and evaluation of a series of benzothiophene. In addition to benzobthiophene, a second isomer is known. Benzothiophene3carboxaldehyde dichloromethyl methyl ether was added dropwise to an icecold solution of 10. Other notes this product has been replaced by t27405aldrich thianaphthene 95%. In summary, we have developed an expedient route for the construction of benzothiophene and indole derivatives via propargylallene rearrangement and allyl migration. The reaction proceeded under mild conditions to produce useful benzothiophene and indole derivatives. The subsequently generated benzothiophenium salts undergo a previously unexplored 1,2. Iodinecatalyzed cascade reactions of substituted thiophenols with alkynes under metal and solventfree conditions enable the synthesis of benzothiophene derivatives in good yields. Benzothiophene is an aromatic organic compound with a molecular formula c 8 h 6 s and an odor similar to naphthalene mothballs. The present method consists of iodocyclization of 1,2bis2methylthiophenylethynes and photolysis of 3iodo2methylthiophenylbenzobthiophenes. An overview of benzo b thiophenebased medicinal chemistry.
Genetic analysis of benzothiophene biodesulfurization. Benzothiophene, benzofuran and indole compounds download pdf. Synthesis and reactions of benzofuran and benzothiophene. 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. Benzothiophene carboxamide derivatives of aminobenzophenone, aminopyridine, aminobenzimidazole, and aniline derivatives compounds 1 9 were synthesized and compounds 3, 6, 7, 8, and 9 tested in vivo for their hypolipidemic activity. Selective derivatization and desulfurization to alkylbenzenes. Such an efficient, economical, and green transformation should provide an attractive approach to various benzothiophenes. For the first time, the synthesis of organosilicon derivatives of dialkyl1benzothieno3,2b1 benzothiophene btbt capable of forming a semiconducting monolayer at the waterair interface is. Benzofuran is basically a heterocyclic compound comprising of fused benzene and furan ring. The present work details the journey towards development of a simple, cost effective, environmentally friendly synthesis of raloxifene hydrochloride 1. Benzothiophene finds use in research as a starting material for the synthesis of larger, usually bioactive structures. Soluble in ethanol, soluble in ether, acetone and general organic solvents, insoluble in water.
Novel benzothiophene 1,1dioxide deoxygenation path for. After two hours 10ml concentrated hcl was added, producing a solid blach mass. The catalytic synthesis of benzothiophene journal of the american. A palladiumcatalyzed ch arylation of electronenriched heteroarenes with aryl bromides and aryl chlorides. A, candidate bdk inhibitor 476i16 identified by highthroughput screening of a 2,000compound chemical library.
Benzothiophene manufacturer, benzothiophene suppliers. View the article pdf and any associated supplements and figures for a period of 48 hours. Benzothiophene carboxylate derivatives as novel allosteric. Aerobic oxidative desulfurization of benzothiophene. B, separation of compound 476i16 into smaller compound fractions bt1 and bt2 by reversedphase hplc. An interrupted pummerer reaction between benzothiophene soxides and the coupling partners yields sulfonium salts that lack aromaticity and therefore allow facile 3,3sigmatropic rearrangement.
All structured data from the file and property namespaces is available under the creative commons cc0 license. Synthesis of benzothiophene carboxamide derivatives and. Abstract four methylbenzothiophenes and two methylnaphthothiophenes were synthesized by cyclization of arylketosulphides obtained by reaction of halogen ketones on thiophenols in the presence o. New benzothiophene derivatives as dual cox12 and 5lox inhibitors. Penthala nr1, sonar vn, horn j, leggas m, yadlapalli js, crooks pa.
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