Heterocyclic Building Blocks-Benzothiophene

Rhodium(III)-Catalyzed Regioselective C-H Annulation and Alkenylation of 2-Pyridones with Terminal Alkynes was written by Li, Jiajie;Xu, Xin;Luo, Zhenli;Yao, Zhen;Yang, Ji;Zhang, Xin;Xu, Lijin;Wang, Peng;Shi, Qian. And the article was included in Advanced Synthesis & Catalysis in 2022.Related Products of 4298-52-6 This article mentions the following:

Cp*Rh(III)-catalyzed regioselective C-H annulation and alkenylation of 2-pyridones with terminal alkynes was developed. The cationic Cp*Rh(III) catalytic system containing FeCl₃ additive enables annulation of 1-(2-pyridyl)-2-pyridones with terminal alkynes, providing efficient access to 5,7-diarylated 2-quinolinones I [R = H, 4-Me, 3-Br, etc.; R¹ = H, 4-Me, 5-F, etc.; Ar = Ph, 2-MeC₆H₄, 2-naphthyl, etc.]. The reaction pathway could be switched to alkenylation with [Cp*RhCl₂]₂ as the catalyst, NaOAc as the additive and HOAc as the solvent, affording C6-alkenylated 1-(2-pyridyl)-2-pyridones II [R² = Ph, 3-MeC₆H₄, 2-naphthyl, etc.; R³ = H, 4-Me, 3-Br, etc.] in high yields. These protocols accommodated a wide range of substrates with good functional group compatibility. In the experiment, the researchers used many compounds, for example, 2-Ethynylthiophene (cas: 4298-52-6Related Products of 4298-52-6).

2-Ethynylthiophene (cas: 4298-52-6) belongs to benzothiophene derivatives. Benzothiophene scaffolds are of great importance due to its increased presence in bioactive molecules. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.Related Products of 4298-52-6

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Synthesis of sulfur isosteres of cholanthrene was written by Faller, Pierre. And the article was included in Comptes Rendus des Seances de l’Academie des Sciences, Serie C: Sciences Chimiques in 1966.Reference of 5118-13-8 This article mentions the following:

The synthesis of I and II is described. 4-Bromobenzo[b]thiophene (III), b₂₀ 144° [1,1-dioxo derivative m. 147° (EtOH)], was prepared from ο-BrC₆H₄CHO via the following intermediates: 5-(ο-bromobenzylidene)rhodanine, m. 189° (EtOH); ο-BrC₆H₄CH:C(SH)CO₂H, m. 147°; [ο-BrC₆H₄CH:C(CO₂H)S]₂, m. 207° (EtOH); and 4-bromobenzo[b]-2-thienoic acid, m. 272° (EtOH). The Grignard reagent from I condensed with 4-cyanoindan and hydrolyzed gave IV, m. 88-9° (petroleum ether) [2,4-dinitrophenylhydrazone m. 234-5° (EtOH)], which subjected at 400-20° during 5-10 min. to an Elbs cyclodehydration under N yielded 10% II, m. 187-8° (EtOH-C₆H₆). 7-Br isomer of III yielded similarly V, m. 86.5° (petroleum ether) [2,4-dinitrophenylhydrazone m. 257° (EtOH-C₆H₆)], which was converted to 40% I, m. 172-3° (EtOH-C₆H₆); 2,4,7-trinitrofluorenone adduct m. 266° (absolute EtOH); picric acid adduct m. 149-50° (absolute EtOH); maleic anhydride adduct m. 251-2° (C₆H₆-petroleum ether). In the experiment, the researchers used many compounds, for example, 4-Bromobenzo[b]thiophene (cas: 5118-13-8Reference of 5118-13-8).

4-Bromobenzo[b]thiophene (cas: 5118-13-8) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The core structure is a part of various pharmaceutical substances and natural products. The different substitution patterns in these heterocycles offer new opportunities for drug discovery and other applications in materials science.Reference of 5118-13-8

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Preheated fly-ash catalyzed aldol condensation: efficient synthesis of chalcones and antimicrobial activities of some 3-thienyl chalcones was written by Arulkumaran, Ranganathan;Vijayakumar, Sambandhamoorthy;Sakthinathan, S. Pazhanivel;Kamalakkannan, Dakshnamoorthy;Ranganathan, Kaliyaperumal;Suresh, Ramamoorthy;Sundararajan, Rajasekaran;Vanangamudi, Ganesan;Thirunarayanan, Ganesamoorthy. And the article was included in Journal of the Chilean Chemical Society in 2013.Formula: C13H10OS This article mentions the following:

In the present study the authors have prepared a series of chalcone derivatives by a solvent-free aldol condensation mediated by microwave irradiation The synthesis of the target compounds was achieved using heat-treated fly ash (ash residue) as a catalyst. The yields of the ketones are more than 60%. The synthesized chalcones were characterized by their anal., phys. and spectral data. The antimicrobial activities of substituted styryl 3-thienyl ketones were studied using the Bauer-Kirby method. The title compounds thus formed included 3-(4-nitrophenyl)-1-(3-thienyl)-2-propen-1-one (I) and related substances, such as 2-thiophene derivatives, naphthalene derivatives, benzenamine derivatives, halobenzene derivatives, phenol derivatives, etc. In the experiment, the researchers used many compounds, for example, 3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one (cas: 3988-77-0Formula: C13H10OS).

3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one (cas: 3988-77-0) belongs to benzothiophene derivatives. Functionalized benzothiophenes are important constructs found in molecules with wide ranging biological activity and in organic materials. It is found within the chemical structures of pharmaceutical drugs such as zileuton, raloxifene, and sertaconazole, and also BTCP.Formula: C13H10OS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Enantioselective Synthesis of Atropisomers Featuring Pentatomic Heteroaromatics by Pd-Catalyzed C-H Alkynylation was written by Zhang, Shuo;Yao, Qi-Jun;Liao, Gang;Li, Xin;Li, Han;Chen, Hao-Ming;Hong, Xin;Shi, Bing-Feng. And the article was included in ACS Catalysis in 2019.Recommanded Product: 113893-08-6 This article mentions the following:

In the presence of Pd(OAc)₂ and L-tert-leucine, biaryl aldehydes containing five-membered rings such as I underwent enantioselective alkynylation with bromoalkynes such as (triisopropylsilyl)bromoacetylene mediated by silver(I) trifluoroacetate in AcOH/toluene to give nonracemic atropisomeric biaryls such as II. A wide range of atropisomers in which either C-N or C-C bonds serve as the atropisomeric axis and containing one or two five-membered rings at each end of the axis were obtained; various five-membered heteroarenes, including pyrroles, thiophenes, benzothiophenes, and benzofurans were compatible with the method. A nonracemic 3,3′-bisbenzothiophene was prepared in 93% ee by this method. DFT calculations of the racemization barriers for various biaryls indicated that the shape of the rings on the biaryl axis is important in determining the racemization barriers. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophen-3-ylboronic acid (cas: 113893-08-6Recommanded Product: 113893-08-6).

Benzo[b]thiophen-3-ylboronic acid (cas: 113893-08-6) belongs to benzothiophene derivatives. Benzothiophene is a fused ring compound of thiophene ring and benzene ring, which is an important class of heterocycles with advantageous structures. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.Recommanded Product: 113893-08-6

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Design and facile synthesis of 6-(benzothiophen-3-yl)-3-para-substituted-[1,2,4] triazolo [3,4-a] phthalazine derivatives as anti-microbial agents was written by Prabhakar, V.;Sudhakar Babu, K.;Ravindranath, L. K.;Lakshmi Reddy, I.;Latha, J.. And the article was included in Research Journal of Chemical Sciences in 2016.Computed Properties of C8H7BO2S This article mentions the following:

The synthesis, characterization and screening the biol. activity of the series of 6-(benzothiophen-3-yl)-3-para-substituted-[1,2,4]triazolo[3,4-a]phthalazines I [R = H, 4-Me, 2,5-di-F, etc.] with good yields were reported. The synthesized compounds I were characterized by IR, ¹H-NMR, ¹³C-NMR and mass spectral data. The anti-microbial activity of the compounds I were screened by disk diffusion method. Compounds I [R = 4-F, 2,5-di-F, 4-F₃C] demonstrated good antimicrobial activity against all the tested microbial strains. Compound I [R = 2,5-di-F] was showed good antibacterial and antifungal activities. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophen-3-ylboronic acid (cas: 113893-08-6Computed Properties of C8H7BO2S).

Benzo[b]thiophen-3-ylboronic acid (cas: 113893-08-6) belongs to benzothiophene derivatives. Benzothiophene finds use in research as a starting material for the synthesis of larger, usually bioactive structures. It is found within the chemical structures of pharmaceutical drugs such as zileuton, raloxifene, and sertaconazole, and also BTCP.Computed Properties of C8H7BO2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Synthesis of Novel Chiral Phosphoric Acid-Bearing Two Acidic Phenolic Hydroxyl Groups and its Catalytic Evaluation for Enantioselective Friedel-Crafts Alkylation of Indoles and Enones was written by Liu, Xiong-Li;Yu, Zhang-Biao;Pan, Bo-Wen;Chen, Lin;Feng, Ting-Ting;Zhou, Ying. And the article was included in Journal of Heterocyclic Chemistry in 2015.Category: benzothiophene This article mentions the following:

A novel chiral phosphoric acid catalyst bearing two acidic phenolic hydroxyl groups was synthesized. Its catalytic activity as a chiral Bronsted acid has been examined in the enantioselective Friedel-Crafts alkylation of indoles and enones as a model reaction. In comparison with the other chiral phosphoric acid catalysts, the reaction catalyzed by the novel chiral catalyst afforded the desired 3-substituted indoles I (R¹ = H, OCH₃, Br; R² = H, CH; R³ = Ph, n-Pr, 2-naphthyl, 2-thienyl, 2-furyl; R⁴ = Ph, CH₃, 2-thienyl, 4-ClC₆H₄, 4-CH₃OC₆H₄) in a higher enantioselectivity (up to 69% ee). In the experiment, the researchers used many compounds, for example, 3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one (cas: 3988-77-0Category: benzothiophene).

3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one (cas: 3988-77-0) belongs to benzothiophene derivatives. Benzothiophene is used as starting material for the synthesis of bioactive molecules. The core structure is a part of various pharmaceutical substances and natural products. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, and sertaconazole, and also BTCP.Category: benzothiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Optimization of synthesis process of 1,3,2-dioxathiolane 2,2-dioxide was written by Wang, Peihong;Zhang, Nan;Zhou, Baoqiang;Gao, Ruichang. And the article was included in Huagong Jinzhan in 2016.Safety of 1,3,2-Dioxathiolane 2,2-dioxide This article mentions the following:

1,3,2-Dioxathiolane 2,2-dioxide is synthesized from ethylene glycol and thionyl chloride in the presence of ruthenium trichloride heterogeneous catalyst and oxidant, and characterized by ¹H NMR and IR. The effects of different oxidants, molar ratio of raw materials, reaction temperature, reaction time, oxidant dosage and catalyst dosage on the yield of target product are investigated. The optimal reaction conditions contain sodium periodate as oxidant, thionyl chloride:ethylene glycol molar ratio of 1.2:1, sodium periodate:ethylene glycol mass ratio of 3:1, catalyst:ethylene glycol mass ratio of 0.002:1, reaction temperature of 40°C and reaction time of 60 min. Under the optimal reaction conditions, the yield of target product reaches 81.25%. The synthesis process has advantages of fewer byproducts, lower toxicity and higher yield, and is more valuable in practical application. In the experiment, the researchers used many compounds, for example, 1,3,2-Dioxathiolane 2,2-dioxide (cas: 1072-53-3Safety of 1,3,2-Dioxathiolane 2,2-dioxide).

1,3,2-Dioxathiolane 2,2-dioxide (cas: 1072-53-3) belongs to benzothiophene derivatives. Benzothiophenes are valuable heterocycles that are widely used in medicines, agrochemicals, and materials science. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, sertaconazole, and also BTCP.Safety of 1,3,2-Dioxathiolane 2,2-dioxide

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Effect of LiPF₆ concentration in Li[Ni_0.4Mn_0.4Co_0.2]O₂/graphite pouch cells operated at 4.5 V was written by Petibon, R.;Madec, L.;Abarbanel, D. W.;Dahn, J. R.. And the article was included in Journal of Power Sources in 2015.Application In Synthesis of 1,3,2-Dioxathiolane 2,2-dioxide This article mentions the following:

The effect of LiPF₆ concentration in the 1 M-2.5 M range was studied in Li[Ni_0.4Mn_0.4Co_0.2O]₂ (NMC(442))/graphite and LaPO₄ coated-NMC(442)/graphite pouch cells cycled to high voltage. Electrochem. impedance spectroscopy on sym. cells revealed that the dramatic impedance growth observed in NMC(442)/graphite cells cycled to high voltage comes from the interface impedance of the pos. electrode. The use of high LiPF₆ concentrations in the 2-2.5 M range dramatically slowed down the impedance growth of both coated and uncoated NMC(442)/graphite cells containing certain electrolyte additive blends and cycled to high voltage. However no beneficial effect was observed in control cells containing no electrolyte additive. X-ray photoelectron spectra of cycled electrodes of coated-NMC(442)/graphite cells showed that LiPF₆ concentration greatly affected the composition of the solid electrolyte interphase of both the pos. and neg. electrodes of cells containing additives. In the experiment, the researchers used many compounds, for example, 1,3,2-Dioxathiolane 2,2-dioxide (cas: 1072-53-3Application In Synthesis of 1,3,2-Dioxathiolane 2,2-dioxide).

1,3,2-Dioxathiolane 2,2-dioxide (cas: 1072-53-3) belongs to benzothiophene derivatives. Benzothiophene is a fused ring compound of thiophene ring and benzene ring, which is an important class of heterocycles with advantageous structures. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.Application In Synthesis of 1,3,2-Dioxathiolane 2,2-dioxide

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Synthesis and S_NV reactions of 2-(haloethenyl)benzo[b]thiophene 1,1-dioxides was written by Gajewski, Robert P.;Jackson, Johnny L.;Jones, Noel D.;Swartzendruber, John K.;Deeter, Jack B.. And the article was included in Journal of Organic Chemistry in 1989.Application In Synthesis of 6-Chlorobenzothiophene This article mentions the following:

The synthesis of a variety of 2-(haloethenyl)benzo[b]thiophenes from both substituted and unsubstituted benzo[b]thiophenes is described. Their corresponding 1,1-dioxides exhibited versatile reactivity via S_NV (addition/conjugated elimination) and direct substitution mechanisms with amine, thio, and alkoxy nucleophiles in good yield. E.g., thianaphthene was lithiated and treated with F₂C:CCl₂ to give I (R = H, R¹ = R² = Cl, n = 0), which was oxidized with H₂O₂ to give I (R’s = same as above, n = 2) (II). Treatment of II with Me₂NH, EtOH, EtSH, and PhSH gave I (R = NEt₂, OEt, SEt, R¹ = H, R² = Cl, n = 2; R = R² = PhS, R¹ = H, n = 2), resp. Among the ∼70 other compounds prepared were I (R = SPr, R¹ = H, R² = NEt₂, n = 0; R = H, R¹ = R² = Br, n = 0, 2; R = NMe₂, R¹ = H, R² = F, n = 2). In the experiment, the researchers used many compounds, for example, 6-Chlorobenzothiophene (cas: 66490-20-8Application In Synthesis of 6-Chlorobenzothiophene).

6-Chlorobenzothiophene (cas: 66490-20-8) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The core structure is a part of various pharmaceutical substances and natural products. It is found within the chemical structures of pharmaceutical drugs such as zileuton, raloxifene, and sertaconazole, and also BTCP.Application In Synthesis of 6-Chlorobenzothiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Raney nickel desulfurization was written by Hurd, Charles D.;Rudner, Bernard. And the article was included in Journal of the American Chemical Society in 1951.Formula: C7H9NO3S This article mentions the following:

Three Raney-Ni preparations were investigated in the desulfuration of S-containing compounds o-Tolyl isothiocyanate or o-tolylthiourea gave o-MeC₆H₄NH₂; PhSO₂ derivative, white plates from 80% EtOH, m. 125-6° and 124-4.5°; Bz derivative, m. 144-5° and 142-3°. There were no secondary amines. Thiobenzanilide gave PhNHCH₂Ph; PhCONHPh, m. 164-6°; benzenesulfon(N-benzylanilide), m. 117-18°; benzo(N-benzylanilide), m. 106.5-107° (white needles from EtOH). 2-Mercaptobenzothiazole gave mostly PhNH₂, with smaller amounts of o-H₂NC₆H₄SH and benzothiazole; picrate, needles from 90% EtOH, m. 178-9.5°. 2-Mercapto- (I) and 2-amino-4-phenylthiazole (II) yielded MeCOPh; 2,4-dinitrophenylhydrazone, m. 246-8°. I also gave 4-phenylthiazole; HCl salt, m. 76-8°; picrate, m. 162-3°. II gave MeNH₂ and PhEtNH. 2-Amino- and 2-mercapto-4-hydroxythiazole gave AcNH₂ and AcH, resp. 2-Thienyl Me ketone gave BuCOMe [2,4-dinitrophenylhydrazone, m. 104-5° (orange-red rods from EtOH)], and small amounts of AcH and EtOH. In the experiment, the researchers used many compounds, for example, 2-Amino-3-hydroxy-3-(thiophen-2-yl)propanoic acid (cas: 32595-59-8Formula: C7H9NO3S).

2-Amino-3-hydroxy-3-(thiophen-2-yl)propanoic acid (cas: 32595-59-8) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The electrophilic substitution of benzothiophene systems is much less regioselective than that of indoles. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.Formula: C7H9NO3S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem