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The kinetics of the hydronium-ion catalysed hydrolysis of the following heterocyclic methyl enol ethers have been measured: 3-methoxybenzofuran, 3-methoxybenzothiophene, 3-methoxyindole, 3-methoxy-1-methylindole, 3-methoxyfuran, 3-methoxythiophene, and 2-methoxythiophene.On the basis of the solvent isotope effect kH/kD = 3.08 and the failure to detect deuterium exchange when the solvent was CD3CN:D2O (9:1 v/v) it was concluded that the rate limiting step in the hydrolysis of 3-methoxybenzofuran is C-protonation.The effect of the ring-oxygen atom was measured by comparing the rate of hydrolysis of 3-methoxybenzofuran with that of 3-methoxyindene which occurs 2100 times faster.In contrast to the behaviour of 3-methoxybenzofuran the isotope effects, kH/kD, for the hydrolyses of 3-methoxyfuran, 3-methoxythiophene, 3-methoxyindole, 3-methoxy-1-methylindole and 2-methoxythiophene are ca 0.4 – 0.5 and deuterium exchange is much faster than hydrolysis when the solvent is CD3CN:D2O (9:1 v/v).It was therefore concluded that with these compound C-protonation is rapid and reversible and that slow step is attack by water on the intermediate cation.

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Reference:
Benzothiophene – Wikipedia,
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Condensation of benzofuran-3(2H-one, benzothiophen-3(2H)-one and benzoselenophen-3(2H)-one with dimedone gives 2-(3-heteryl)dimedones.Acylation of the latter leads to the corresponding tetracyclic pyrylium salts, from which condensed quinolines are obtained.Some condensed quinoline derivatives are obtained by reaction of 1-oxo-1,2,3,4-tetrahydroheterene<2,3-c>quinolines with sodiuum borohydride, hydrazine, and hydroxylamine.

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Reference:
Benzothiophene – Wikipedia,
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The invention concerns compounds of formula (I) in which: A forms a tricyclic system of formula A1, A2, A3 or A4; R1 represents a hydrogen atom, an alkyl, hydroxy, alkoxy or oxo group; (R2)m and (R3)m?are such as defined in the description; n represents an integer such that 0<=n<=3; p represents an integer such as defined in the description; B represents a group (a) or (b). The invention is useful for preparing medicines. A reaction mechanism is the microscopic path by which reactants are transformed into products. Each step is an elementary reaction. In my other articles, you can also check out more blogs about 130-03-0 Reference:
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Abstract Two novel metal free organic dyes based on thioindigo were prepared and used as sensitizers in dye-sensitized solar cells. The synthesized dyes together with their corresponding intermediates were purified and characterized by analytical techniques. Such techniques confirmed the corresponding structures of dyes and their intermediates and the yield of all the stages of dye preparation were calculated to be above 75%. Fluorometric analyses show fluorescence in the red region of the visible spectrum for both dyes. Oxidation potential measurements for both dyes ensured an energetically permissible and thermodynamically favourable charge transfer throughout the continuous cycle of photo-electric conversion. Finally, dye sensitized solar cells were fabricated in order to determine the photovoltaic behaviour and conversion efficiencies of each dye. Such evaluations demonstrate rather high conversion efficiencies of 6.10% and 6.45% for such simple structured dyes 1 and 2, respectively.

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Benzothiophene – Wikipedia,
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A series of tetracyclic quinoline- and quinoxalinecarboxamides were prepared, and their cytotoxicities were evaluated in a series of murine human tumor cell lines. Most of the quinoline derivatives were prepared by an adaptation of the Pfitzinger synthesis, followed by thermal decarboxylation and coupling with N,N-dimethylethylenediamine via a mixed anhydride method using isobutyl chloroformate. The quinoline analogues showed cytotoxicities broadly similar to those of the known tricyclic acridine-4-carboxamide mixed topoI/II inhibitor DACA, with thieno and indeno analogues being the most active. They showed little decrease in potencies against the Jurkat human leukemia topo II-resistant lines JL(A) and JL(C), suggesting their cytotoxicity does not result primarily from inhibition of topo II. The quinoxaline analogues had more varied IC50 values, being on average less cytotoxic than the quinoline derivatives, but appeared to have a similar mode of action. Overall, this new class of compounds appear to be mixed topo I/II inhibitors, up to 3-fold more cytotoxic than DACA in the human leukemia cell lines studied, with in vivo activity in colon 38 comparable to that of DACA and doxorubicin.

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Benzothiophene – Wikipedia,
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The synthesis and principal properties of alpha-(2-thionaphthenylmercapto)-propionic acids as well as of some of their derivatives have been described.Racemic acid was resolved by crystallization of its diastereometric salts with optically active bases.The asymmetric transformation of laevorotatory alpha-bromopropionic acid to delta(+)alpha-(2-thionaphthenylmercapto)-propionic acid was carried out.The absolute configurations of the enantiomers were elucidated.Optical rotatory dispersion of the laevorotatory enantiomer and its p-bromophenacyl and p-phenylphenacyl esters in the region 365HPLC of Formula: C8H6OS

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Benzothiophene – Wikipedia,
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Anodic fluorination of benzo[b]thiophene derivatives provided a complex mixture of di- and trifluorinated products. On the other hand, anodic fluorination of 3-oxo-2,3-dihydrobenzo[b]thiophene and methyl 3-oxo-2,3-dihydrobenzo[b]thiophene-2-carboxylate gave the corresponding monofluorinated products selectively in moderate yields. Anodic fluorination of methyl alpha-(2-cyanophenylthio)acetate followed by intramolecular cyclization provided 3-amino-2-fluorobenzo[b]thiophene in excellent yield. Georg Thieme Verlag Stuttgart · New York.

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Benzothiophene – Wikipedia,
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A systematic investigation of reductive ring expansion reaction of oximes with diisobutylaluminum hydride (DIBAH) was performed. The reaction regiospecifically provided a variety of unsubstituted bicyclic heterocycles 3a-3g or tricyclic heterocycles 3h, 3j-3l that contained nitrogen attached to an aromatic ring.

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(Chemical Equation Presented) The synthesis of 5- to 8-memebered cyclic thioethers 4 has been achieved through a simple two-step sequence. The present methodology utilizes the facile Friedel-Crafts acylation of terminal alkynes 1 with acid chlorides 2 followed by tandem C(sp3)-S and C(sp 2)-S bond formations with NaSH·xH2O.

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The carbonyl group present in benzothiophen-3-ones 4, 3,4- dihydrothiopyrano[3,2-b]benzothiophen-4(2H)-ones 11 and 3,4-dihydro-2H,5H- thiopyrano[2′,3′ : 4,5]thiopyrano[3,2-b]benzothiophen4-ones 16 has been made use to develop 1,2,3-selena and thiadiazoles via their semicarbazones by the reaction with selenium dioxide and thionyl chloride. The IR, H NMR and C, H analyses has been utilized to characterize the new compounds.

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Reference:
Benzothiophene – Wikipedia,
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