Properties and Exciting Facts About Benzo[b]thiophen-3(2H)-one

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Synthesis of new merocyanine dyes of thiophene series

Reaction of benzo[b]thiophen-3(2H)-one or thieno[2,3-b]pyridin-3(2H)-one with diarylpropargylic alcohols gives new merocyanine dyes.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

Extracurricular laboratory:new discovery of Benzo[b]thiophen-3(2H)-one

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Organocatalytic Asymmetric Formal Aza-[3+3]Cyclo-additions of 3-Aminobenzofuran with alpha,beta-Unsaturated Aldehydes

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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Benzothiophene – Wikipedia,
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Reaction of 6-methoxybenzo[b]furan-3(2H)-one and benzo[b]thiophen-3(2H) -one with 2-aryl-1,1-dicyanoethylenes as a convenient synthetic route to substituted 2-amino-4-aryl-1,3-dicyano-7-methoxydibenzo[b,d]furans and 2-amino-4-aryl-3-cyano-4H-benzothieno[3,2-b]pyrans

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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Benzothiophene – Wikipedia,
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Making fast photoswitches faster – Using hammett analysis to understand the limit of donor-acceptor approaches for faster hemithioindigo photoswitches

Hemithioindigo (HTI) photoswitches have a tremendous potential for biological and supramolecular applications due to their absorptions in the visible-light region in conjunction with ultrafast photoisomerization and high thermal bistability. Rational tailoring of the photophysical properties for a specific application is the key to exploit the full potential of HTIs as photoswitching tools. Herein we use time-resolved absorption spectroscopy and Hammett analysis to discover an unexpected principal limit to the photoisomerization rate for donor-substituted HTIs. By using stationary absorption and fluorescence measurements in combination with theoretical investigations, we offer a detailed mechanistic explanation for the observed rate limit. An alternative way of approaching and possibly even exceeding the maximum rate by multiple donor substitution is demonstrated, which give access to the fastest HTI photoswitch reported to date. An unexpected principal limit to the photoisomerization rate for donor-substituted hemithioindigos (HTIs; see figure) has been discovered; this provides a quantitative estimate for the highest possible photoisomerization rate. A mechanistic explanation for the observed limit is offered together with an alternative way of approaching the maximum rate by multiple donor substitution. This approach gave access to the fastest HTI photoswitch reported to date.

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Benzothiophene – Wikipedia,
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THE TAUTOMERISM OF HYDROXY DERIVATIVES OF FIVE-MEMBERED OXYGEN, NIRTOGEN, AND SULFUR HETEROCYCLES

The unstable enolic tautomers 3-hydroxyfuran, 2- and 3-hydroxy-thiophene, 3-hydroxy-pyrrole, 3-hydroxy-1-methyl-pyrrole and their benzo-derivatives have been generated in solution and the rate and equilibrium constants for their ketoization determined.

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Benzothiophene – Wikipedia,
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Polycyclicpolythia compounds: Benzothiophen-3-one as potential synthon for the synthesis of 3,4-dihydro-2H,5H-thiopyrano<2',3':4,5>thiopyrano<3,2-b>benzothiophen-4-one – Part II

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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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Intramolecular S¡¤¡¤¡¤O chalcogen bond in thioindirubin

Results of X-ray diffraction study and quantum-chemical calculations revealed that molecular conformation of thioindirubin molecule creates suitable conditions for formation of intramolecular C-H¡¤¡¤¡¤O and S¡¤¡¤¡¤O interactions. Analysis of molecular electrostatic potential (MEP) demonstrates existence of two areas of positive MEP (sigma-holes) in the outermost part of the sulfur atom on the continuation of the lines of the C-S bonds. One of these sigma-holes is oriented toward region of negative MEP around the oxygen atom of carbonyl group. Such situation corresponds to formation of sigma-hole or chalcogen bond. Existence of both types of bonding interactions is confirmed by topological analysis of electron density distribution using “Atoms in Molecules” (AIM) theory. Energies of the C-H¡¤¡¤¡¤O hydrogen bond and the S¡¤¡¤¡¤O sigma-hole bond derived from AIM and NBO theories are very close.

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Reference£º
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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CYCLOCONDENSATION OF 3(2H)-BENZOTHIOPHENONE AND OXIDATION PRODUCTS OBTAINED DURING THESE REACTIONS

The cyclocondensation of 3(2H)-benzothiophenone under acidic conditions has been studied.The symmetrical cyclotrimer tris(benzothieno)<2,3:2',3':2'',3''>benzene was formed and under certain conditions also a rearranged cyclotrimer, tris(benzothieno)<2,3:2',3':3'',2''>benzene.The formation of cyclotrimers was accompanied by oxidative coupling products involving the initially formed dimeric compound, 3-hydroxy-2,3-bibenzothienyl.During several of these reactions, a novel heterocycle, tris(benzothieno)<3,2-b:2',3'-d:2'',3''-f>oxepin, was formed.The products were studied by mass spectrometry and fragmentation pathways were determined by a linked scanning technique.

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Benzothiophene – Wikipedia,
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INHIBITORS OF ESTROGEN RECEPTOR ALPHA AND THEIR USE AS THERAPEUTICS FOR CANCER

This invention provides of compounds having structures of Formula A, uses of these compounds for treatment of various indications, including breast cancer, as well as methods of treatment involving these compounds.

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Brief introduction of Benzo[b]thiophen-3(2H)-one

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Application of 130-03-0, Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 130-03-0, molcular formula is C8H6OS, introducing its new discovery.

One-step synthesis of thioaurones

A rapid, one-step preparation of 2-(arylmethylidene)-1-benzothiophen-3-ones (thioaurones) using directed alpha-metallation, ring closure and aldol-type condensation is described. The reaction leads exclusively to the Z-isomer.

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Reference£º
Benzothiophene – Wikipedia,
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