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Ni-Mediated Generation of “cN” Unit from Formamide and Its Catalysis in the Cyanation Reactions

The in situ generation of a “cyano” unit from readily available organic precursors is of high interest in synthetic chemistry. Herein, we report the first example of Ni-mediated dehydration of formamide to form “CN” and its subsequent catalytic applications in the hydrocyanation of alkynes and cyanation of aryl halides. Formamide can serve as a convenient source for the nitrile unit, in that it releases water as the only byproduct.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

Discovery of 5-Bromobenzothiophene

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CYCLOALKYLNITRILE PYRAZOLE CARBOXAMIDES AS JANUS KINASE INHIBITORS

Cycloalkylnitrile pyrazole carboxamides as JAK inhibitors useful for the treatment of JAK-mediated diseases such as rheumatoid arthritis, asthma, COPD and cancer are provided

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Benzothiophene – Wikipedia,
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Synthesis, transition temperatures, and optical properties of various 2,6-disubstituted naphthalenes and related 1-benzothiophenes with butylsulfanyl and cyano or isothiocyanato terminal groups

Fourteen compounds based on 2,6-disubstituted naphthalenes or related 1-benzothiophene moieties with butylsulfanyl and cyano or isothiocyanato terminal groups have been synthesised. The transition temperatures of the compounds and their refractive indices have been determined and the derived values for the optical anisotropies, polarisabilities and order parameters have been calculated. With one exception (which also shows a smectic A phase), all the compounds with naphthyl and phenyl groups are solely nematogenic; for these compounds the naphthyl unit gives an average increase in T(N-I) value and melting point of 72 and 20C respectively compared to the values for the compounds with a phenyl in place of the naphthyl unit. The incorporation of a 2,5-thiophene unit in place of phenyl lowers T(N-I) and when it is part of a 1-benzothiophene unit the depression is even greater. The naphthalene compounds increase the values of optical anisotropy by approximately 0.04, compared to the phenyl systems, mainly because they increase the refractive index of the e-ray (n values); compound 12 has an exceptionally high optical anisotropy (Deltan value) of 0.54.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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NOVEL ANTHRANILIC ACID DERIVATIVE OR SALT THEREOF

The anthranilic acid derivative or the salt thereof represented by the general formula wherein R1 and R2 are hydrogen atom, or the like; R3 is a phenyl, cycloalkyl or bicyclic heterocyclic group which may be substituted, or the like; R4 is a phenyl, cycloalkyl or pyridyl group which may be substituted, or the like; X1 is an alkylene or alkenylene group which may be substituted or a bond; X2 is the general formula -X3-X4- or -X4-X3-, wherein X3 is a sulfur atom, an imino group or a bond, or the like; X4 means an alkylene or alkenylene group which may be substituted or a bond; is useful for a remedy such as rheumatoid arthritis, osteoarthritis and carcinoma, because it shows MMP-13 production inhibitory effect.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Modular Synthesis of Di- A nd Trisubstituted Imidazoles from Ketones and Aldehydes: A Route to Kinase Inhibitors

A one-pot and modular approach to the synthesis of 2,4(5)-disubstituted imidazoles was developed based on ketone oxidation, employing catalytic HBr and DMSO, followed by imidazole condensation with aldehydes. This methodology afforded twenty-nine disubstituted NH-imidazoles (23%-85% yield). A three-step synthesis of 20 kinase inhibitors was achieved by employing this oxidation-condensation protocol, followed by bromination and Suzuki coupling in the imidazole ring to yield trisubstituted NH-imidazoles (23%-69%, three steps). This approach was also employed in the synthesis of known inhibitor GSK3037619A.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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RhCl3-Catalyzed Oxidative C-H/C-H Cross-Coupling of (Hetero)aromatic Sulfonamides with (Hetero)arenes

1,1?-Bi(hetero)aryl 2-sulfonamide scaffolds have been widely used as a privileged structure in drug discovery. Herein, we report an efficient rhodium-catalyzed oxidative C-H/C-H cross-coupling between a (hetero)aromatic sulfonamide and a (hetero)arene to afford ortho-sulfonamido bi(hetero)aryls. This methodology features broad substrate scope, good functional group tolerance, and relatively inexpensive catalyst (without the use of RhCp). A wide range of (hetero)arenes such as thiophenes, benzothiophenes, pyrroles, furans, benzofuran, indolizine, and simple arenes can engage in this transformation. This protocol also provides a facile route to bi(hetero)aryl sultams and dibenzo[b,d]thiophene 5,5-dioxides through further intramolecular cyclization, indicating its potential application in materials exploitation.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Palladium-Catalyzed alpha-Arylation of Carboxylic Acids and Secondary Amides via a Traceless Protecting Strategy

A novel traceless protecting strategy is presented for the long-standing challenge of conducting the palladium-catalyzed alpha-arylation of carboxylic aids and secondary amides with aryl halides. Both of the presented coupling processes occur with a variety of carboxylic acids and amides and with a variety of aryl bromides containing a broad range of functional groups, including base-sensitive functionality like acyl, alkoxycarbonyl, nitro, cyano, and even hydroxyl groups. Five commercial drugs were prepared through this method in one step in 81-96% yield. Gram-scale synthesis of medication Naproxen and Flurbiprofen with low palladium loading further highlights the practical value of this method.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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USE OF BENZO-HETEROARYL SULFAMIDE DERIVATIVES FOR THE TREATMENT OF PAIN

The present invention is a method for the treatment of pain comprising administering to a subject in need thereof a therapeutically effective amount of one or more novel benzo-heteroaryl sulfamide derivatives of formula (I) as herein defined. The present invention is further directed to methods for the treatment of pain comprising co-therapy with analgesic agent(s) and a compound of formula (I) as described herein.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Enzymatic enantioselective decarboxylative protonation of heteroaryl malonates

The enzyme aryl/alkenyl malonate decarboxylase (AMDase) catalyses the enantioselective decarboxylative protonation (EDP) of a range of disubstituted malonic acids to give homochiral carboxylic acids that are valuable synthetic intermediates. AMDase exhibits a number of advantages over the non-enzymatic EDP methods developed to date including higher enantioselectivity and more environmentally benign reaction conditions. In this report, AMDase and engineered variants have been used to produce a range of enantioenriched heteroaromatic alpha-hydroxycarboxylic acids, including pharmaceutical precursors, from readily accessible alpha-hydroxymalonates. The enzymatic method described here represents an improvement upon existing synthetic chemistry methods that have been used to produce similar compounds. The relationship between the structural features of these new substrates and the kinetics associated with their enzymatic decarboxylation is explored, which offers further insight into the mechanism of AMDase. Versatile decarboxylase: Aryl malonate decarboxylase (AMDase) and engineered variants have been shown to catalyse the enatioselective decarboxylative protonation of a range of alpha-heteroaryl alpha-hydroxy malonates with excellent yields and enantioselectivity (see scheme).

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Organic light emitting compd. and organic electroluminescence element using the same (by machine translation)

The present invention relates to a novel indole-based compound having excellent hole injection and transport capabilities, light-emission, and other properties, and to an organic electroluminescent device the luminous efficiency, driving voltage, service life, and other characteristics of which are improved due to containing the compound in one or more organic material layers.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem