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The total synthesis of 3,4-dihydro-2H,5H-thiopyrano<2',3':4,5>thiopyrano<3,2-b>benzothiophen-4-one (9) from benzothiophen-3-one (4) has been described.

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New Advances in Chemical Research in 2021. Catalysts allow a reaction to proceed that has a lower activation energy than the uncatalyzed reaction. In heterogeneous catalysis, catalysts provide a surface to which reactants bind in a process of adsorption. Computed Properties of C8H6OS. Introducing a new discovery about 130-03-0, Name is Benzo[b]thiophen-3(2H)-one

The most red-shifted hemithioindigo photoswitches have been identified through systematic introduction of aryl units to a parent pyrrole hemithioindigo photoswitch. Increasing the size of the 5?-aryl substituent is ineffective at producing further redshifted chromophores. A second generation of 3?,5?-diarylated photoswitches which possess increased tunability is reported. Experimental and computational evidence indicates the 4? position is electronically isolated from the bulk of the conjugated system.

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General procedure: Under an inert atmosphere of argon, a solution of 9 mmol of Component 4 or Component 5 together with 5 mmol of thioindoxyl in 15 mL of methanol was vigorously stirred and to which small portions of Na2CO3 was added. After 1 h of stirring at 45 C, the dark red residue was filtered and successively and intensively washed with methanol and cold water. The resulting precipitate was filtered and purified by silica gel column chromatography (ethyl acetate:hexane 1:2)., 130-03-0

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Reference:
Article; Hosseinnezhad, Mozhgan; Moradian, Siamak; Gharanjig, Kamaladin; Dyes and Pigments; vol. 123; (2015); p. 147 – 153;,
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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Benzothiophene – Wikipedia,
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Catalysts allow a reaction to proceed via a pathway that has a lower activation energy than the uncatalyzed reaction. In heterogeneous catalysis, catalysts provide a surface to which reactants bind in a process of adsorption. 130-03-0, name is Benzo[b]thiophen-3(2H)-one. In an article,Which mentioned a new discovery about 130-03-0, name: Benzo[b]thiophen-3(2H)-one.

gamma-Radiolysis of aqueous benzothiophene solutions saturated with N2O has been studied.In the absence of other reagents, the only products detected are 2- and 3-hydroxybenzothiophene and their corresponding lactonic and ketonic tautomers and a small amount of dimeric species.In the presence of potassium hexacyanoferrate or sodium hydroxide, however, products attributable to hydroxylation at all six available carbon sites are detected and dimer formation is reduced.Analysis of the experimental data suggests that both benzothiophene and its hydroxylation products are efficient scavengers for the radiation-produced OH radicals and that the initial yield of hydroxylation products is equal to that of hydroxyl radicals.Consistent with the electrophilic characteristics of the OH radical, k(OH+C8H6S):k(OH+C8H5SOH)=0.5+/-0.1.All six available carbon sites are capable of forming OH adducts, but the radicals formed by addition to the 4, 5, 6, and 7 positions tend to revert to the original compound or its ion in a neutral or acidic medium.In the case of the adducts formed by addition to the thiophene ring, on the other hand, the 3 position is seen to be favored, possibly as the result of the preservation of the aromatic benzene resonance structure.

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Benzothiophene – Wikipedia,
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An important 13C NMR shielding effect on carbons bearing a heavy chalcogen is demonstrated.This effect is parallel to that induced by iodine, but to a lesser extent.For acyclic compounds and for partially saturated heterocycles, there is an excellent linear correlation between the 13C chemical shifts of carbons bearing a chalcogen and carbons bearing a halogen atom in the corresponding compound.The linearity of the relationship is less satisfactory with heteroaromatic compounds.

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3-Oxo-2,3-dihydrobenzo[b]furans, -thiophenes and -selenophenes 1a-c afforded the bromo-aldehydes 2 under Vilsmeier-Haack-Arnold conditions. Palladium-catalysed aryl-aryl coupling of 2 with o-formyl-phenylboronic acid allowed the formation of dialdehydes 3 which underwent McMurry cyclisation or pinacol condensation to yield polycyclic aromatic derivatives 4 or the dihydroxylated compounds 5.

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Benzothiophene – Wikipedia,
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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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The condensation of ethyl sarcosinate on 2- or 3-halogeno 3- or 2-formyl<1>benzofuran, benzothiophene or benzoselenophene, and on the related 2H-<1>-3-benzoheterocyclanones is described.In the last instances the resulting compounds were formylated in the 2-position with subsequent cyclodehydration.After hydrolysis and decarboxylation, the 1-methyl<1>benzothieno-, benzoseleno<2,3-b>pyrroles and the 1-methyl<1>benzofuro, benzothieno- and benzoseleno<3,2-b>pyrroles were thus obtained.

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Benzothiophene – Wikipedia,
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The O-deuterated enolic tautomers 3-deuteroxybenzofuran, 3-deuteroxybenzothiophene, 3-deuteroxyindole, 3-deuteroxy-1-methylindole, 3-deuteroxyfuran, 3-deuteroxythiophene, 2-deuteroxybenzothiophene, and 2-deuteroxythiophene have been generated in solution in mixtures of CD3COCD3, CD3CN, or CD3SOCD3 with D2O by hydrolysis of their trimethylsilyl derivatives in the presence of DCl (1E-3 – 1E-4 M) and characterized by 1H NMR spectroscopy.Solutions of 3-hydroxypyrrole and of 3-hydroxy-1-methylpyrrole were obtained by methanolysis of their trimethylsilyl derivatives,evaporation of the methanol, and immediate dissolution in DMSO-d6.The carbocyclic analogues of the bicyclic heterocyclic enols 3-deuteroxyindene and 2-deuteroxyindene were also generated in solution.Attempts to prepare solutions of 2-deuteroxyfuran, 2-deuteroxypyrrole, and 2-deuteroxy-1-methylpyrrole were unsuccessful.The kinetics of ketonization of the OH forms of these enols have been investigated in water or aqueous acetonitrile solution.The equilibrium constants for the keto-enol tautomerism were also determined either by direct measurement when sufficient enol was present at equilibrium or as the ratio of the rate constant for enolization of the keto form to that for ketonization of the enol form, the former being determined by the iodine-trapping technique.The effect of solvent on the equilibrium constants was also studied.Sufficient data were available for the equilibrium between 3-hydroxyindole and 3-ketoindole for them to be analyzed by the four-parameter equation of Mills and Beak to yield an a value of 2.4 and a b value of -3.0.The pKas of the bicyclic enols were measured. 3-Hydroxybenzofuran and3-hydroxybenzothiophene are stronger acids than 3-hydroxyindole and 3-hydroxy-1-methylindole.The ketonization reactions are general acid and general base catalyzed and their mechanisms are discussed.

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Benzothiophene – Wikipedia,
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