Tag: 100-200

Synthesis of thiophenes and thiapyrans. III. Hydroxythianaphthenes and alkoxythianaphthenes was written by Sunthankar, A. V.;Tilak, B. D.. And the article was included in Proceedings – Indian Academy of Sciences, Section A in 1951.Formula: C9H8OS This article mentions the following:

Monomethoxythianaphthalenes are prepared by condensing a mercaptoanisole with BrCH₂CH(OMe)₂ (I) and effecting a ring closure of the resulting sulfide. p-MeOC₆H₄SH (7.6 g.), 1.2 g. Na, 1.25 g. NaI, 9.3 g. I, and 25 cc. absolute alc. boiled 2 h., and the crude product distilled yields 70% p-methoxyphenyl 2,2-dimethoxyethyl sulfide (II), b_2.5-3 155-60°; dinitrophenylhydrazone, m. 106-7°. From 6.1 g. II added to 30 g. P₂O₅ and 10 cc. H₃PO₄ at 150-60°/0.34 mm. is obtained 5-methoxythianaphthene (isolated as the picrate), which after distillation forms a white solid, m. 42-3°, b_0.52 85-90°; the yield is poor. Similarly prepared were m-methoxyphenyl 2,2-dimethoxyethyl sulfide, b_2.5 125-30° (2,4-dinitrophenylhydrazone, m. 123-4°); 6-methoxythianaphthene, b₁₆ 153-6° (62% yield)(picrate, m. 105-6°); o-methoxyphenyl 2,2-dimethoxyethyl sulfide, b₁₅ 175-80° (2,4-dinitrophenylhydrazone, m. 135-6°); 7-methoxythianaphthene, (III), b₁₅ 140-5° (yield 18%)(picrate, m. 110-11°); p-ethoxyphenyl 2,2-dimethoxyethyl sulfide, b₁₂ 180° (2,4-dinitrophenylhydrazone, m. 84-5°); 5-ethoxythianaphthene, b₁₂ 145° (picrate, m. 93°); 3-methoxy-p-toluenethiol, b₁₂ 130°; 3-methoxy-4-methylphenyl 2,2-dimethoxyethyl sulfide, b₁₅ 185° (2,4-dinitrophenylhydrazone, m. 123-4°); 6-methoxy-5-methylthianaphthene (IV), m. 62-3°, b₁₂ 160° (picrate, m. 107-8°); 6-methoxy-5-methylthianaphthene 1,1-dioxide (from 0.45 g. IV, 7 cc. glacial AcOH, and 3 cc. H₂O₂ heated 6 h. at 85°), m. 187°. Demethylation of 0.62 g. III with 5 g. pyridine-HCl by heating 9 h. at 180° gave 0.5 g. (88%) 7-hydroxythianaphthene, b₈ 135°, m. 67-8° (picrate, m. 184-6°); from IV by the same procedure is obtained 6-hydroxy-5-methylthianaphthene, m. 146-7°, b₁₀ 160-5°. All b.ps. are given as bath temperature In the experiment, the researchers used many compounds, for example, 6-Methoxybenzo[b]thiophene (cas: 90560-10-4Formula: C9H8OS).

6-Methoxybenzo[b]thiophene (cas: 90560-10-4) belongs to benzothiophene derivatives. Benzothiophenes are valuable heterocycles that are widely used in medicines, agrochemicals, and materials science. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization.Formula: C9H8OS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

A highly efficient one-pot reaction of 2-(gem-dibromovinyl)phenols(thiophenols) with K₄Fe(CN)₆ to 2-cyanobenzofurans(thiophenes) was written by Zhou, Wei;Chen, Wei;Wang, Lei. And the article was included in Organic & Biomolecular Chemistry in 2012.HPLC of Formula: 55219-11-9 This article mentions the following:

2-Cyanobenzofurans and 2-cyanobenzothiophenes I [R = H, 5-Me, 5-tBu, etc.; X = O, S] were prepared through an efficient one-pot Ullmann-reaction/cyanation reaction. In the presence of CuI/Na₂CO₃-Pd(OAc)₂/PPh₃ in DMF, the reaction of 2-(gem-dibromovinyl)phenols and 2-(gem-dibromovinyl)thiophenols with K₄Fe(CN)₆, as nontoxic and user-friendly cyanating reagent, proceeded smoothly to generate the corresponding 2-cyanobenzofurans and 2-cyanobenzothiophenes in good yields. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9HPLC of Formula: 55219-11-9).

Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9) 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 raloxifene, zileuton, and sertaconazole, and also BTCP.HPLC of Formula: 55219-11-9

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

2-(2-Thienyl)-5,6-dihydroxy-4-carboxypyrimidines as Inhibitors of the Hepatitis C Virus NS5B Polymerase: Discovery, SAR, Modeling, and Mutagenesis was written by Koch, Uwe;Attenni, Barbara;Malancona, Savina;Colarusso, Stefania;Conte, Immacolata;Di Filippo, Marcello;Harper, Steven;Pacini, Barbara;Giomini, Claudia;Thomas, Steven;Incitti, Ilario;Tomei, Licia;De Francesco, Raffaele;Altamura, Sergio;Matassa, Victor G.;Narjes, Frank. And the article was included in Journal of Medicinal Chemistry in 2006.Electric Literature of C9H5NS This article mentions the following:

Infections caused by hepatitis C virus (HCV) are a significant world health problem for which novel therapies are in urgent demand. The polymerase of HCV is responsible for the replication of viral RNA. The authors recently disclosed dihydroxypyrimidine carboxylates as novel, reversible inhibitors of the HCV NS5B polymerase. This series was further developed into 5,6-dihydroxy-2-(2-thienyl)pyrimidine-4-carboxylic acids such as (I) (EC₅₀ 9.3 μM), which now show activity in the cell-based HCV replication assay. The structure-activity relation of these inhibitors is discussed in the context of their physicochem. properties and of the polymerase crystal structure. We also report the results of mutagenesis experiments which support the proposed binding model, which involves pyrophosphate-like chelation of the active site Mg ions. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9Electric Literature of C9H5NS).

Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9) belongs to benzothiophene derivatives. Benzothiophene finds use in research as a starting material for the synthesis of larger, usually bioactive structures. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.Electric Literature of C9H5NS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Potential hypolipidemic agents. XX. Synthesis and lipid-lowering properties of annelated thiophenecarboxylic acids was written by Gronowitz, Salo;Herslof, Margareta;Svenson, Rolf;Bondesson, Goran;Magnusson, Olle;Stjernstrom, Nils E.. And the article was included in Acta Pharmaceutica Suecica in 1978.Quality Control of 5-Fluoro-1-benzothiophene-2-carboxylic acid This article mentions the following:

Condensed thiophenecarboxylic acids I–V (R = H, Cl, F; R¹ = H, Cl; R² = H, Cl, F, Me, R³ = H; R² = H, R³ = Cl) were prepared The V had anticholesteremic and hypolipemic activity superior that of clofibrate, whereas IV was inactive. Chlorination increased the hypolipemic activity of I through III. In the experiment, the researchers used many compounds, for example, 5-Fluoro-1-benzothiophene-2-carboxylic acid (cas: 70060-13-8Quality Control of 5-Fluoro-1-benzothiophene-2-carboxylic acid).

5-Fluoro-1-benzothiophene-2-carboxylic acid (cas: 70060-13-8) 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 zileuton, raloxifene, and sertaconazole, and also BTCP.Quality Control of 5-Fluoro-1-benzothiophene-2-carboxylic acid

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Design, synthesis, and biological activity evaluation of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives as broad-spectrum antifungal agents was written by Zhao, Liyu;Sun, Yin;Yin, Wenbo;Tian, Linfeng;Sun, Nannan;Zheng, Yang;Zhang, Chu;Zhao, Shizhen;Su, Xin;Zhao, Dongmei;Cheng, Maosheng. And the article was included in European Journal of Medicinal Chemistry in 2022.Synthetic Route of C9H5FO2S This article mentions the following:

To discover antifungal compounds with broad-spectrum and stable metabolism, a series of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives were designed and synthesized. Compounds I [R¹ = 6-F, 6-Cl, 6-Br; R² = 4-F] and [R¹ = 6-Cl, 6-Br; R² = 4-Cl] exhibited excellent broad-spectrum antifungal activity against Candida albicans with MIC values in the range of 0.03-0.5μg/mL, and against Cryptococcus neoformans and Aspergillus fumigatus with MIC values in the range of 0.25-2μg/mL. In addition, compounds I [R¹ = 6-Cl; R² = 4-F] and [R¹ = 6-Cl; R² = 4-Cl] showed high metabolic stability in human liver microsomes in vitro, with the half-life of 80.5 min and 69.4 min, resp. Moreover, compounds I [R¹ = 6-Cl; R² = 4-F] and [R¹ = 6-Cl; R² = 4-Cl] showed weak or almost no inhibitory effect on the CYP3A4 and CYP2D6. The pharmacokinetic evaluation in SD rats showed that compoundI [R¹ = 6-Cl; R² = 4-F] had suitable pharmacokinetic properties and was worthy of further study. In the experiment, the researchers used many compounds, for example, 5-Fluoro-1-benzothiophene-2-carboxylic acid (cas: 70060-13-8Synthetic Route of C9H5FO2S).

5-Fluoro-1-benzothiophene-2-carboxylic acid (cas: 70060-13-8) belongs to benzothiophene derivatives. Benzothiophene finds use in research as a starting material for the synthesis of larger, usually bioactive structures. It is also used in the manufacturing of dyes such as thioindigo.Synthetic Route of C9H5FO2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Thiocyanate radical mediated dehydration of aldoximes with visible light and air was written by Ban, Yong-Liang;Dai, Jian-Ling;Jin, Xiao-Ling;Zhang, Qing-Bao;Liu, Qiang. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2019.Name: Benzo[b]thiophene-2-carbonitrile This article mentions the following:

Herein, a new means of activating aldoximes by an in situ generated thiocyanate radical from ammonium thiocyanate and mol. oxygen at room temp has been discussed. With a catalytic amount of organic dye aizenuranine as the photocatalyst, the dehydration of aldoximes proceeds smoothly under visible light irradiation, providing a simple to handle, excellent functional group tolerance, and metal-free protocol for a wide range of nitriles. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9Name: Benzo[b]thiophene-2-carbonitrile).

Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The electrophilic substitution of benzothiophene systems is much less regioselective than that of indoles. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization.Name: Benzo[b]thiophene-2-carbonitrile

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Nickel-catalyzed hydrogenolysis of unactivated carbon-cyano bonds was written by Patra, Tuhin;Agasti, Soumitra;Modak, Atanu;Maiti, Debabrata. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2013.Name: Benzo[b]thiophene-2-carbonitrile This article mentions the following:

Selective hydrogenolysis of C-CN bonds can allow chemists to take advantage of ortho-directing ability, α-C-H acidity, and electron withdrawing ability of the cyano group for synthetic manipulations. We have discovered hydrogenolysis of aryl and aliphatic cyanides under just 1 bar of hydrogen by using a nickel catalyst. E.g., in presence of Ni(COD)₂, tricyclohexylphosphine, and AlMe₃, hydrogenolysis of aromatic nitrile (I) gave 79% II. This protocol was applied in the aryl cyanide directed functionalization reaction and α-substitution of benzyl cyanides. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9Name: Benzo[b]thiophene-2-carbonitrile).

Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The electrophilic substitution of benzothiophene systems is much less regioselective than that of indoles. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, sertaconazole, and also BTCP.Name: Benzo[b]thiophene-2-carbonitrile

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Practical one-pot transformation of electron-rich aromatics into aromatic nitriles with molecular iodine and aqueous NH₃ using Vilsmeier-Haack reaction was written by Ushijima, Sousuke;Moriyama, Katsuhiko;Togo, Hideo. And the article was included in Tetrahedron in 2012.Reference of 55219-11-9 This article mentions the following:

Various electron-rich aromatics could be efficiently transformed into the corresponding aromatic nitriles in good to moderate yields by treatment with DMF and POCl₃, followed by the reaction with mol. iodine or 1,3-diiodo-5,5-dimethylhydantoin (DIH) in aqueous NH₃. Some of the less reactive aromatics, such as anisole, 1,2-dimethoxybenzene, 1,4-dimethoxybenzene, and mesitylene, could also be transformed into the corresponding aromatic nitriles in good to moderate yields using N-methylformanilide and O(POCl₂)₂, followed by reaction with mol. iodine in aqueous NH₃. Moreover, propiophenone derivatives could be successfully transformed into the corresponding β-chlorocinnamonitriles by the reaction with DMF and POCl₃, followed by the reaction with mol. iodine and aqueous NH₃. These reactions are novel metal-free one-pot methods for the preparation of aromatic nitriles from electron-rich aromatics and β-chlorocinnamonitriles from propiophenones. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9Reference of 55219-11-9).

Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9) belongs to benzothiophene derivatives. Benzothiophenes are valuable heterocycles that are widely used in medicines, agrochemicals, and materials science. The different substitution patterns in these heterocycles offer new opportunities for drug discovery and other applications in materials science.Reference of 55219-11-9

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem