Heterocyclic Building Blocks-Benzothiophene

Chen, Lu published the artcileA modular biomimetic strategy for the synthesis of macrolide P-glycoprotein inhibitors via Rh-catalyzed C-H activation, Name: 3-Acetylthiophene, the main research area is allyl alc preparation diastereoselective chemoselective; vinylethylene carbonate preparation carboxylic acid allylation rhodium catalyst.

An Rh(III)-catalyzed native carboxylic acid-directed and solvent-free C-H activation allylation with high stereoselectivity and chemoselectivity is achieved. The generated poly-substituted allylic alc., e.g., I as a multifunctional and biomimetic building block is crucial for the synthesis of (Z)-allylic-supported macrolides, e.g., II. Moreover, the unique allylic-supported macrolides significantly potentiate the sensitivity of tumor cells to cytotoxic agents such as vinorelbine and docetaxel by reversing p170-glycoprotein-mediated MDR.

Nature Communications published new progress about Allylation catalysts, stereoselective (chemoselective). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Name: 3-Acetylthiophene.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Lecoeur, Sylvaine published the artcileSpecificity of in vitro Covalent Binding of Tienilic Acid Metabolites to Human Liver Microsomes in Relationship to the Type of Hepatotoxicity: Comparison with Two Directly Hepatotoxic Drugs, Name: 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, the main research area is tienilate metabolite binding liver microsome hepatotoxicity; cytochrome P4502C9 tienilate binding antibody formation.

To better understand the first steps leading to drug-induced immunoallergic hepatitis, the authors studied the target of anti-LKM2 autoantibodies appearing in tienilic acid-induced hepatitis, and the target of tienilic acid-reactive metabolites. It was identified as cytochrome P 450 2C9, (P 450 2C9): indeed,anti-LKM2 specifically recognized P 450 2C9, but none of the other P450s tested (including other 2C subfamily members, 2C8 and 2C18). Tienilic acid-reactive metabolite(s) specifically bound to P 4502C9, and experiments with yeast expressing active isolated P450s showed that P 450 2C9 was responsible for tienilic acid-reactive metabolite(s) production Results of qual. and quant. covalent binding of tienilic acid metabolite(s) to human liver microsomes were then compared to those obtained with two drugs leading to direct toxic hepatitis, namely, acetaminophen and chloroform. Kinetic constants (Km and Vmax) were measured, and the covalent binding profile of the metabolites to human liver microsomal proteins was studied. Tienilic acid had both the lowest Km and the highest covalent binding rate at pharmacol. doses. For acetaminophen and chloroform, several microsomal proteins were covalently bound, while covalent binding was highly specific for tienilic acid and dihydralazine, another drug leading to immunoallergic hepatitis. Although low numbers of drugs were tested, these results led the authors to think that there may exist a relation between the specificity of covalent binding and the type of hepatotoxicity.

Chemical Research in Toxicology published new progress about Autoantibodies, monoclonal Role: BIOL (Biological Study). 40180-04-9 belongs to class benzothiophene, name is 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, and the molecular formula is C13H8Cl2O4S, Name: 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Nicholson, Kieran published the artcileA Boron-catalyzed, Diastereo- and Enantioselective Allylation of Ketones with Allenes, Recommanded Product: 3-Acetylthiophene, the main research area is homoallylic alc preparation diastereoselective regioselective enantioselective mechanistic study; allene ketone allylation boron catalyst.

Here, a boron-catalyzed allylation of ketones R1C(O)R2 (R1 = Ph, furan-2-yl, benzodioxol-5-yl, etc.; R2 = Me, 4-fluorophenyl) and 1-indanone with allenes R3C(R4)=C=CH2 [R3 = cyclohexyl, phenylethyl, Me; R4 = H, Me; R3R4 = -(CH2)5-] is presented. Excellent yield, regioselectivity and diastereoselectivity were found across functionalized allylic alcs. R(R1)C(OH)C(R3)(R4)CH=CH2 and 1-(3-cyclohexylprop-1-ene)indanol. The reaction was further developed to accommodate an enantioenriched boron catalyst and thus gave asym. ketone allylation in good yield allylic alcs., diastereoselectivity and enantioselectivity. Mechanistic studies supported a hydroboration-allylation-transborylation pathway.

ACS Catalysis published new progress about Allenes Role: RCT (Reactant), RACT (Reactant or Reagent). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Recommanded Product: 3-Acetylthiophene.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Zhao, Yiming published the artcileBalancing Bulkiness in Gold(I) Phosphino-triazole Catalysis, Recommanded Product: 3-Acetylthiophene, the main research area is crystal structure phosphinotriazole gold chloro complex; gold triazolylphosphine preparation catalyst alkyne hydration cross coupling; Click chemistry; Gold; Homogeneous catalysis; Phosphane ligands; Triazoles.

The syntheses of 1-phenyl-5-phosphino 1,2,3-triazoles are disclosed, within which, the P atom (at the 5-position of a triazole) is appended by one, two or three triazole motifs, and the valency of the P(III) atom is completed by two, one or zero ancillary (Ph or cyclohexyl) groups, resp. This series of phosphines was compared with tricyclohexylphosphine and PPh3 to study the effect of increasing the number of triazoles appended to the central P atom from zero to three triazoles. Au(I) chloride complexes of the synthesized ligands were prepared and analyzed by techniques including single-crystal x-ray diffraction structure determination Au(I) complexes were also prepared from 1-(2,6-dimethoxy)-phenyl-5-dicyclohexyl-phosphino 1,2,3-triazole and 1-(2,6-dimethoxy)-phenyl-5-diphenyl-phosphino 1,2,3-triazole ligands. The crystal structures thus obtained were examined using the SambVca (2.0) web tool and percentage buried volumes determined The effectiveness of these Au(I) chloride complexes to serve as precatalysts for alkyne hydration were assessed. Also, the regioselectivity of hydration of but-1-yne-1,4-diyldibenzene was probed.

European Journal of Organic Chemistry published new progress about Alkynes Role: RCT (Reactant), RACT (Reactant or Reagent). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Recommanded Product: 3-Acetylthiophene.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Tran, Khoa M. published the artcileSynthesis of primary N-arylthioglyoxamides from anilines, elemental sulfur and primary C-H bonds in acetophenones, Name: 3-Acetylthiophene, the main research area is ketothioamide preparation; aniline sulfur aryl methyl ketone oxidative coupling.

A simple method for coupling of anilines, acetophenones and elemental sulfur to afford α-ketothioamides RNHC(S)C(O)R1 [R = cyclohexyl, Ph, 2-ClC6H4, etc.; R1 = 2-MeOC6H4, 3-BrC6H4, 2-thienyl, etc.] was developed. Reactions proceeded in the presence of Na2SO3 and DMSO, thus eliminating the need for transition metals and external oxidants. Functionalities such as halogen, ester, methylthio, and heterocycle groups were compatible with the conditions. Electron-poor acetophenones sometimes gave isosteric glyoxamides.

RSC Advances published new progress about Anilines Role: RCT (Reactant), RACT (Reactant or Reagent). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Name: 3-Acetylthiophene.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Qin, Zemin published the artcileConstruction of a Pyrimidine Framework through [3 + 2 + 1] Annulation of Amidines, Ketones, and N,N-Dimethylaminoethanol as One Carbon Donor, Quality Control of 1468-83-3, the main research area is pyrimidine preparation green chem; amidine ketone dimethylaminoethanol three component annulation copper bromide.

An efficient, facile, and eco-friendly synthesis of pyrimidine derivatives has been developed. It involves a [3 + 2 + 1] three-component annulation of amidines, ketones, and one carbon source. N,N-Dimethylaminoethanol is oxidized through C(sp3)-H activation to provide the carbon donor. One C-C and two C-N bonds are formed during the oxidative annulation process. The reaction shows good tolerance to many important functional groups in air, making this methodol. a highly versatile alternative, and significant improvement to the existing methods for structuring a pyrimidine framework, especially 4-aliphatic pyrimidines.

Journal of Organic Chemistry published new progress about Amidines Role: RCT (Reactant), RACT (Reactant or Reagent). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Quality Control of 1468-83-3.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Gu, Jia-Yi published the artcilePhotoinduced umpolung addition of carbonyl compounds with α,β-unsaturated esters enables the polysubstituted γ-lactone formation, Recommanded Product: 3-Acetylthiophene, the main research area is unsaturated ester carbonyl compound iridium photocatalyst umpolung addition transesterification; aryl lactone diastereoselective preparation.

The photoinduced intermol. umpolung addition of aromatic ketones/aldehydes with α,β-unsaturated esters via ketyl radical intermediates was reported. Following an intramol. transesterification, a variety of γ-lactone derivatives were readily accessed. Mechanistic investigations demonstrated the significant role of Hantzsch ester, which served both as the electron and proton donor.

Chemical Communications (Cambridge, United Kingdom) published new progress about Addition reaction catalysts, stereoselective (photochem.). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Recommanded Product: 3-Acetylthiophene.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Feng, Zengqiang published the artcileVisible-Light-Promoted Synthesis of α-CF2H-Substituted Ketones by Radical Difluoromethylation of Enol Acetates, Computed Properties of 1468-83-3, the main research area is difluoro arylketone preparation; enol acetate triphenylphosphonium bromide iridium catalyst phtochem radical difluroalkylaion.

An efficient and novel visible-light-promoted radical difluoromethylation of enol acetates for the synthesis of α-CF2H-substituted ketones were described. Upon irradiation under blue LED with catalytic amounts of fac-Ir(ppy)3, this photocatalytic procedure employed difluoromethyltriphenylphosphonium bromide as a radical precursor. Various α-CF2H-substituted ketones were successfully created via designed systems based on the SET process. The methodol. were provided an operationally simple process with broad functional group compatibility.

Organic Letters published new progress about Acetates Role: RCT (Reactant), RACT (Reactant or Reagent). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Computed Properties of 1468-83-3.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Kumar, Togiti Uday published the artcileApplication of Polyphosphoric Acid-Mediated Acyl Migration for Regiospecific Synthesis of Diverse 2-Acylpyrroles from Chalcones, Formula: C6H6OS, the main research area is chalcone preparation toluenesulfonylmethyl isocyanide Van Leusen reaction; acylpyrrole preparation polyphosphoric acid catalyst regioselective intermol transacylation.

A metal-free approach for the synthesis of 2-acylpyrroles was reported. Synthesis of the target mol. started from chalcones and carried out in two steps. Initial step involved the conversion of chalcones to corresponding 4-substituted-3-acylpyrroles by reaction with TosMIC. In the subsequent step, target mols. were obtained in modest to good yields by polyphosphoric acid-mediated acyl rearrangement of 3-acylpyrroles to their 2-acyl congeners. The crucial final step was amenable to diverse substitutions on pyrrole ring. Preliminary experiment for the determination of mechanism indicated the involvement of acylium ion.

Journal of Heterocyclic Chemistry published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Formula: C6H6OS.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Amberchan, Gabriella published the artcileReaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups, Related Products of benzothiophene, the main research area is alc preparation; amine tertiary preparation; tertiary amide reduction diisobutylaluminum borohydride preparation; aldehyde reduction diisobutylaluminum borohydride preparation; epoxide reduction diisobutylaluminum borohydride preparation; carboxylic acid reduction diisobutylaluminum borohydride preparation; ester reduction diisobutylaluminum borohydride preparation; secondary alc preparation; ketone reduction diisobutylaluminum borohydride preparation; primary amine preparation; nitrile reduction diisobutylaluminum borohydride preparation.

The binary hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], synthesized from diisobutylaluminum hydride (DIBAL) and borane di-Me sulfide (BMS) has shown great potential in reducing a variety of organic functional groups. This unique binary hydride, (iBu)2AlBH4, is readily synthesized, versatile, and simple to use. Aldehydes e.g., benzaldehyde, ketones e.g., 2-octanone, esters e.g., Et 3-phenylpropionate, and epoxides e.g., cyclohexeneoxide are reduced very fast to the corresponding alcs. viz., benzyl alc., 2-octanol, 3-phenylpropan-1-ol and cyclohexanol resp. in essentially quant. yields. This binary hydride can reduce tertiary amides e.g., N,N-diethylbenzamide rapidly to the corresponding amine, N,N-diethylbenzylamine at 25°C in an efficient manner. Furthermore, nitriles e.g., benzonitrile are converted into the corresponding amine, 4-methylbenzyl amine in essentially quant. yields. These reactions occur under ambient conditions and are completed in an hour or less. The reduction products are isolated through a simple acid-base extraction and without the use of column chromatog. Further investigation showed that (iBu)2AlBH4 has the potential to be a selective hydride donor as shown through a series of competitive reactions. Similarities and differences between (iBu)2AlBH4, DIBAL, and BMS are discussed.

Journal of Organic Chemistry published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Related Products of benzothiophene.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem