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The reactions of 6-methoxybenzo[b]furan-3(2H)-one with 2-aryl-1,1- dicyanoethylenes and malononitrile or with aromatic aldehyde and two moles of malononitrile afford 2-amino-4-aryl-1,3-dicyano-7-methoxydibenzo[b,d]furans. The reactions of benzo[b]thiophen-3(2H)-one with 2-aryl-1,1-dicyanoethylenes or with aromatic aldehyde and one mole of malononitrile produce 2-amino-4-aryl-3-cyano-4H-benzothieno[3,2-b]pyrans.

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Reference:
Benzothiophene – Wikipedia,
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13C NMR spectra of the title compounds have been fully assigned.The results have been compared with those relative to other chalcogenated compounds, such as anisole, phenyl benzoate, benzofuran,… and their analogs.In chalcogenochromones and -coumarines, the heteroatom lone pair delocalization spreads to some extent over the heterocyclic part of the molecules, while in chalcogenochromanones and -indoxyles, it only extends to the homocycle.This electronic effect seems also to affect the heavy atom effect exhibited by Te-containing compounds.

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Reference:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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A short, simple and expedient synthesis of substituted benzo[b]thiophenes involving directed ortho lithiation-side-chain deprotonation-cyclisation-reduction is described. This method is a valuable improvement over earlier syntheses of the same class of compounds, both with respect to the number of steps and overall yields.

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Benzothiophene – Wikipedia,
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Substituted aurones were found to have antitrypanosomal, antifungal and immunomodulatory activity. The invention provides novel aurone compounds, pharmaceutical compositions, and methods encompassing medical and veterinary applications.

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Friedel-Crafts acylation of arenes with methylthio- (1) or phenylthio-acetyl chloride (2) provides ready access to alpha-methylthio- or alpha-phenylthio-substituted acetophenones.The acyl chlorides 1 and 2 reacted also with organoaluminium reagents to give alpha-sulfenylated alkanones.

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Benzothiophene – Wikipedia,
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The synthesis of highly substituted 1,3-dienes from the coupling of vinyl bromides with vinyl triflates is reported for the first time. The coupling is catalyzed by a combination of (5,5?-bis(trifluoromethyl)-2,2?-bipyridine)NiBr2 and (1,3-bis(diphenylphosphino)propane)PdCl2 in the presence of a zinc reductant. This method affords tetra- and penta-substituted 1,3-dienes that would otherwise be difficult to access and tolerates electron-rich and -poor substituents, heterocycles, an aryl bromide, and a pinacol boronate ester. Mechanistically, the reaction appears to proceed by an unusual zinc-mediated transfer of a vinyl group between the nickel and palladium centers.

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Reference:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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A series of achiral 3-heteroaryl substituted quinuclidin-2-ene derivatives and related compounds have been synthesized by facile methods. The compounds were evaluated for muscarinic and antimuscarinic properties in receptor binding studies using (-)-[3H]-QNB as the radioligand and in a functional assay using isolated guinea pig urinary bladder. 3-(2-Benzofuranyl)-quinuclidin-2-ene (15) displayed the highest M1-receptor affinity in the present series (K(i) = 9.6 nM).

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Benzothiophene – Wikipedia,
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An organocatalytic asymmetric formal aza-[3+3]cycloaddition of readily available N-Tosyl-3-aminobenzofuran with alpha,beta-unsaturated aldehydes was developed for the first time. This method enables the facile synthesis of biologically active and synthetically challenging polysubstituted fused benzofuran derivatives bearing two stereocenters in high yields with excellent diastereo-, and enantioselectivity (up to >20 : 1 dr, and >99% ee). (Figure presented.).

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Stopping cancer in its tracks Thia-analogues of indirubin-N-glycosides, prepared by condensation of N-glycosylisatines with thiaindane-3-one and subsequent deprotection, were tested for their activity against malignant melanoma cells. These indirubin-N-glycoside thia-analogues are active against melanoma cells, inducing growth arrest, apoptosis and inhibition of intracellular signal transduction.

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Reference:
Benzothiophene – Wikipedia,
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The title compounds were obtained by BF3-assisted reactions of 1-benzothiophen-3(2H)-one with nine ketones in diethyl ether at room temperature in moderate to high yields. The pyran 1 and ylidene 2 ratios prove to be dependent upon electronic and steric factors.

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Benzothiophene – Wikipedia,
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