New benzothiophene derivatives as dual cox12 and 5lox. Chemical on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. Simultaneous inhibition of 5loxcox may enhance antiinflammatory effects and reduce side effects. 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. Read synthesis of indole, benzofuran and benzothiophene by reaction of 2anilinoethanol, 2phenoxyethanol and 2phenylthioethanol on alpo 4 and pdalpo 4 catalysts, journal of molecular catalysis a. Synthesis and antitubercular activity of 3substituted. The direct synthesis of benzothiophene3carboxylic acid from benzothiophene utilizing friedelcrafts acylation with trichloroacetyl chloride, followed by basic hydrolysis is presented. The results showed that this compound exhibited reversible photochromism, changing from colorless to yellow after irradiation with uv light both in solution and in pmma amorphous film. The structures of all the products were characterized by nmr, ir, hrms together with xray crystallographic analysis. Find msds or sds, a coa, data sheets and more information.
Takahiro soeta, saori shitaya, takumi okuno, shuhei fujinami, yutaka ukaji. Press, in comprehensive heterocyclic chemistry ii, 1996. Pdf synthesis and characterization of selective dopamine. A mixture of benzobthiophene3carbaldehyde 8 1 mole and the appropriate substituted phenylacetonitrile reactant 1. Synthesis of benzothiophenefused pyran derivatives via. Synthesis of benzothiophene and indole derivatives through. Regioselective synthesis of c3 alkylated and arylated. The reaction of substituted buta1enes with potassium sulfide enables an atom economical, and transitionmetalfree synthesis of thiophenes via cleavage of multiple ch bonds. Preparation of 3amino6fluorobenzothiophene2carbohydrazide 2 to a stirred solution of methyl3amino6fluorobenzothiophene2carboxylate 1 2. Azaindole, benzofuran, and benzothiophene analogs of l741,626.
It occurs naturally as a constituent of petroleumrelated deposits such as lignite tar. Benzothiophene derivatives were synthesized regioselectively using coupling reactions and electrophilic cyclization reactions. Synthesis of benzothiophene carboxamide derivatives and. Evaluation of benzothiophene carboxamides as analgesics. Electrochemical behavior of methyl 3chloro, bromo and iodo1benzothiophene2carboxylates 1 3, and of their reduction and dimer products 4, 5 in anhydrous dimethylformamide has been investigated at mercury and platinum electrodes using polarography, cyclic voltammetry and. Synthesis of 1 provided the first test for this route. Beilstein journal of organic chemistry 2017, 18661870.
Synthesis, properties of a photochromic diarylethene. Hence versatile synthetic strategies are needed to discover the properties of this molecule. Synthesis and evaluation of a series of benzothiophene. Antimicrobial properties of isolated compounds were tested against indicator microorganisms such as c. Synthesis of benzothiophene analogues of ketoconazole and. Moreover, the latter process has been adapted to accomplish the synthesis of indole, benzofuran, and benzothiophene derivatives 23, 27, and 28, respectively. Benzothiophene2boronic acid mida ester 95% sigmaaldrich.
Synthesis of zbenzobthiophene acrylonitriles57 and 911. 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. Synthesis of sheterocycles benzofused sheterocycles synthesis of benzothiophenes. Synthesis and cycloaddition reaction of 3vinylthieno3,2b1benzothiophene. The target compounds were designed to hybridize benzothiophene scaffold or its bioisostere benzofuran with various antiinflammatory pharmacophore. The synthesis of the benzothiophene analogues of the orally active antifungal agents ketoconazole and itraconazole 3a and 3b is reported.
To address this, we have attempted heteroatom oxygen functionalization of btbt by a concise and easily scalable. College of biological, chemical sciences and engineering, jiaxing university, jiaxing 314001, p. Owing to a peculiar hyperconjugation effect, the innate reactivity of haloglycines became the key to crack open the vault, revealing new treasures of amino acids. The 1,3dipolar cycloaddition of azomethine ylides derived from isatin and sarcosine to z2arylmethylidene1benzothiophen32h ones afforded novel dispiro1benzothiophene2,3pyrrolidine2,3indoline2,3diones in moderate yields. Benzobthiophene, benzothiophene, thionaphthene cas number 95158. The chemistry of sulphone hydrazide has gained increase interest in both synthetic organic chemistry and biological fields and has considerable value. We report the subsequent functionalization of this compound into iodine, boronic ester and silane derivatives, which are useful intermediates for various applications. On the other hand, other groups of compounds such as benzophenone, aminopyridine, and amisynthesis of benzothiophene carboxamide derivatives and. Hence, synthesis of novel dual inhibitors of 5loxcox is an important strategy for treatment of inflammation. A preparative method of synthesis of the new methyl 3iodo1benzothiophene2carboxylate was elaborated.
Synthesis and antimicrobial activity of benzothiophene. A new domino reaction between thioaurones and malononitrile has been reported. There have been numerous examples of utilizing thiophene derivatives, both of natural and synthetic origins, for a variety of. 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. Derivatives of benzobthiophenes are useful precursors for the synthesis of thioindigo and azo disperse dyes. A palladiumcatalyzed ch arylation of electronenriched heteroarenes with aryl bromides and aryl chlorides proceeds in the presence of liotbu as a base. Thiophene is ppt on a modest synthesis of around alkylthiols to provide thiophene trifluoroborates in high pdf with. We examined substitution at the c3 position of the benzothiophene1,1.
As illustrated in scheme 3, deprotonation at 5position of 2chlorothiophene, followed by trapping with tmscl generated 3. Benzothiophene is regarded as a privileged class of structure showing a wide spectrum of biological activities. Specialized thiophenes can be synthesized similarly using lawessons reagent such as a bright counter and display endosymbiotic hypothesis quizlet medical terminology on a synthesis than pdf. A new photochromic diarylethene compound, 12methylbenzofuran22,4dimethyl5thiazolyl perfluorocyclopentene 1o, was synthesized, and its photochromic reactivity, fluorescent were also investigated. Synthesis of dispiro1benzothiophene2,3pyrrolidine2. Researcharticle synthesis of benzothiophenefused pyran derivatives via piperidine promoted domino reaction shihangli,aiminyu,jianfali,andxiangtaimeng.
An overview of benzo b thiophenebased medicinal chemistry. Synthesis and properties of isoindigo and benzo1,2b. The applications of thiophene and benzothiophene derivatives were not well exemplified in the first edition of comprehensive heterocyclic chemistry checi. A direct synthesis of benzothiophene3carboxylic acid from benzothiophene. Benzothiophene finds use in research as a starting material. Moreover, the strategy can also be used for the synthesis of thiophenes from 1,4diaryl1,3dienes. Pdf synthesis and reactions of sulphone hydrazides. The crystalstructure, electrochemical and photochemical properties of this compound were determined. A new unsymmetrical photochromic diarylethene 12methyl3benzothiophene22methyl51,3 dioxolane 3 thienyl perfluorocyclopentene 1o has been synthesized. The present method consists of iodocyclization of 1,2bis2methylthiophenylethynes and photolysis of 3iodo2methylthiophenylbenzobthiophenes. Our findings demonstrate that newly synthesized bromo.
Synthesis of benzothiophene and indole derivatives through metalfree propargylallene rearrangement and allyl migration. Differently substituted 2,5diarylthiazole can be obtained with the same catalyst system by switching the solvent and the. Synthesis and characterization of selective dopamine d2 receptor antagonists. Benzothiophene is an aromatic organic compound with a molecular formula c 8 h 6 s and an odor similar to naphthalene mothballs. A direct synthesis of benzothiophene3carboxylic acid. A welldefined series of long and soluble isoindigo thienoacene oligomers have been synthesized from a novel electron deficient building block. Synthesis and antimicrobial activities of benzothiophene derivatives article pdf available in journal of the chilean chemical society 571. Synthesis and application of 12methyl3benzothiophene.
With 1,2bis2methylthiophenylethynes treated with i2phioac2 in ch2cl2 at room temperature, selective cyclization at sulfur took place to. Synthesis of benzothiophene derivatives by pdcatalyzed or. In the meantime, its photochromic, kinetics and fluorescence properties were investigated in detail. Its various derivatives are useful as pesticides, fungicides, and herbicides. The results showed this compound exhibited reversible photochromism, undergoing reversible cyclization and cycloreversion. The three patterns of reactivity observed for the o. The therapeutic importance of these compounds is the attractive force to continue research in such a point. Synthesis of c2 substituted benzothiophenes via an. 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. A new synthetic method for 1benzothieno3,2b1benzothiophene derivatives btbts was developed. Synthesis of 3chloron02hydroxy6 pentadecylbenzylidenebenzothiophene 2carbohydrazide gadada naganagowda, patchanita thamyongkit, runchana klaiudom, orathip pengsakut, amorn petsom research center for bioorganic chemistry rcbc, department of chemistry, faculty of science, chulalongkorn university, bangkok 10330, thailand.
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