Day: February 10, 2023

Benzothiophene or Benzofuran Bridges in Diaryl Ethenes: Two-Step Access by Pd-Catalyzed C-H Activation and Theoretical/Experimental Studies on Their Photoreactivity was written by Yuan, Kedong;Boixel, Julien;Chantzis, Agisilaos;Jacquemin, Denis;Guerchais, Veronique;Doucet, Henri. And the article was included in Chemistry – A European Journal in 2014.Safety of 2,3-Dibromobenzo[b]thiophene This article mentions the following:

A series of terarylenes incorporating benzothiophene (BT)/benzofuran (BF) as the central ethene unit was synthesized by using sequential Pd-catalyzed C-H activation reactions. This new methodol. allows the easy modification of the nature of the pendant heteroarene groups. Diaryl ethene (DAE) derivatives with thiophene, thiazole, pyrrole, isoxazole and pyrazole rings were prepared A large number of asym. DAEs are easily accessible by this new method in both the BT and BF series. The study of their photochromic properties in solution revealed that the nature of the heteroarene and of the central unit drastically modify their photochromic behavior. TD-DFT calculations were performed to assess the nature of the relevant excited states. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Safety of 2,3-Dibromobenzo[b]thiophene).

2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7) 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.Safety of 2,3-Dibromobenzo[b]thiophene

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.Application of 7312-11-0 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, Methyl 5-bromobenzo[b]thiophene-2-carboxylate (cas: 7312-11-0Application of 7312-11-0).

Methyl 5-bromobenzo[b]thiophene-2-carboxylate (cas: 7312-11-0) 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.Application of 7312-11-0

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Benzo[b]thiophene-2-carboxamide derivatives as potent urotensin-II receptor antagonists was written by Lim, Chae Jo;Woo, Seong Eun;Ko, Su Ik;Lee, Byung Ho;Oh, Kwang-Seok;Yi, Kyu Yang. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2016.Application of 7312-11-0 This article mentions the following:

Members of a series of benzo[b]thiophene-2-carboxamide derivatives, possessing an N-(1-(3-bromo-4-(piperidin-4-yloxy)benzyl)piperidin-4-yl) group, were synthesized and evaluated as urotensin-II receptor antagonists. The results show that these substances have potent UT binding affinities. Observations made in a systematic SAR investigation of the effects of a variety of substituents at the 5- and 6-positions in the benzo[b]thiophene-2-carboxamide moiety on UT binding affinities led to identification of the 5-cyano analog I as a highly potent UT antagonist with an IC₅₀ value of 25 nM. Despite having a good metabolic stability, compound I is a potent inhibitor of CYP isoenzyme and displays an unsuitable PK profile. In the experiment, the researchers used many compounds, for example, Methyl 5-bromobenzo[b]thiophene-2-carboxylate (cas: 7312-11-0Application of 7312-11-0).

Methyl 5-bromobenzo[b]thiophene-2-carboxylate (cas: 7312-11-0) 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 has been used as a raw material for the synthesis of biologically active structures and is found in pharmaceuticals such as leukotriene synthesis inhibitors and antifungals, as well as in many natural products.Application of 7312-11-0

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Acetylation of 2-bromo-3-methyl- and 3-bromo-2-methylthianaphthene and the Schmidt reaction of the products was written by Matsuki, Yasuo;Ito, Ichi. And the article was included in Nippon Kagaku Zasshi in 1967.Safety of 3-Bromo-2-methylbenzo[b]thiophene This article mentions the following:

2-Bromo-3-methylthianaphthene (11.4 g.) in 35 ml. PhNO2 was treated with 4.35 g. AcCl and 7.35 g. AlCl3 at 10° to give 9.2% 4-acetyl-2-bromo-3-methylthianaphthene (I), m. 123-4°, 2,4-dinitrophenylhydrazone m. 278° (decomposition), 67.4% Ia (R1 = Br, R2 = Me, R3 = Ac) (II), m. 114-15°; 2,4-dinitrophenylhydrazone m. 270-1°, and 19.1% Ia (R1 = Ac, R2 = Me, R3 = H) (III). Reaction at 25° gave 9.9% I, 72.7% II and 26.6% III. Similar reaction of 3-bromo-2-methylthianaphthene gave 94.1% Ia (R1 = Me, R2 = Br, R3 = Ac), m. 96-7°, 2,4-dinitrophenylhydrazone m. 282° (decomposition), at 0° and 80.6% 3-acetyl-2-methylthianaphthene at 10°. The results were attributed to the electron density at 3 position. II (1 g.) was dissolved in 80 ml. MeOH containing 0.23 g. NaOH and hydrogenated over Pd-C to yield 0.66 g. Ia (R1 = H, R2 = Me, R3 = Ac), m. 42-3°; 2,4-dinitrophenylhydrazone m. 282° (decomposition). II (2.7 g.) was treated with KClO (3.8-4 g.) in 30-5 ml. H2O and 20 ml. dioxane at 55-60° and then at 80° to give 2.62 g. Ia (R3 = CO2H) (Ib, R1 = Br, R2 = Me) (IV), m. 261-2°; Me ester m. 131-2°. Similarly the following Ib were obtained (R1, R2, m.p. and m.p. of Me ester given): H, Me, 226-7°, -; Me, Br (V), 272-3°, 98-9°; Me, H, 228-9°, 48-9°. Heating IV with Raney Ni yielded p-iso-PrC6H4CO2H. Similarly V gave p-PrC6H4CO2H. II (4.04 g.) in 19.5 ml. AcOH and 1.95 g. H2SO4 was treated with 1.95 g. NaN3 at 65-70° to give 63% Ia (R1 = Br, R2 = Me, R3 = AcNH) (VI), m. 196-7°, and 13% Ia (R1 = Br, R2 = Me, R3 = NH2) sulfate, m. 234°. Similarly the following Ia were obtained (R1, R2, R3, % yield, m.p. of the acetamido derivative, % yield and m.p. of amine sulfate given): Me, Br, AcNH, 71, 181.5-2°, 19, 272° (decomposition); AcNH, Me, H, 50, 180-1°, -, -; Me, AcNH, H, 82, 184-5°, -, -. Reduction of VI with Na-Hg gave 6-acetamido-3-methylthianaphthene. 2-(N-Methylcarbamoyl)-3-methylthianaphthene, m. 139-40°, and 3-(N-methylcarbamoyl)-2-methylthianaphthene, m. 166-7°, were prepared In the experiment, the researchers used many compounds, for example, 3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9Safety of 3-Bromo-2-methylbenzo[b]thiophene).

3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The core structure is a part of various pharmaceutical substances and natural products. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization.Safety of 3-Bromo-2-methylbenzo[b]thiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Practical Synthesis of Photochromic Diarylethenes in Integrated Flow microreactor Systems was written by Asai, Tatsuro;Takata, Atsushi;Nagaki, Aiichiro;Yoshida, Jun-ichi. And the article was included in ChemSusChem in 2012.Safety of 3-Bromo-2-methylbenzo[b]thiophene This article mentions the following:

An effective method for the synthesis of photochromic diarylethenes through the generation of heteroaryllithiums and subsequent reaction with octafluorocyclopentene has been developed by using integrated flow microreactor systems. Reactions can be conducted without using cryogenic conditions by virtue of effective temperature and residence time control, although much lower temperatures (<-78 °C) are needed for batch macroreactions. Moreover, the synthesis of unsym. diarylethenes, which is difficult to achieve when using conventional batch macrosystems, has been accomplished based on the selective introduction of one aryl group to give arylheptafluorocyclopentene followed by the introduction of another aryl group. The productivity of the laboratory-scale system is approx. 0.5 mmol min^-1. Therefore, the present integrated flow microreactor method serves as a practical way of synthesizing various photochromic diarylethene derivatives In the experiment, the researchers used many compounds, for example, 3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9Safety of 3-Bromo-2-methylbenzo[b]thiophene).

3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9) 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.Safety of 3-Bromo-2-methylbenzo[b]thiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Concise Synthesis of Highly Substituted Benzo[a]quinolizines by a Multicomponent Reaction/Allylation/Heck Reaction Sequence was written by den Heeten, Rene;van der Boon, Leon J. P.;Broere, Daniel L. J.;Janssen, Elwin;de Kanter, Frans J. J.;Ruijter, Eelco;Orru, Romano V. A.. And the article was included in European Journal of Organic Chemistry in 2012.Category: benzothiophene This article mentions the following:

The combination of the recently developed multicomponent construction of highly substituted 3,4-dihydropyridones with subsequent allylation and intramol. Heck-type cyclization allows the straightforward construction of benzo[a]quinolizines, a class of polycyclic compounds that – despite their interesting pharmacol. and photochem. properties – have little precedent in the literature. After optimization of the individual steps, we used this reliable three-step sequence to generate a small library of diversely substituted benzo[a]quinolizines and various heterocyclic analogs. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Category: benzothiophene).

2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7) 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.Category: benzothiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Synthesis and photochromism studies of 1-(2-methyl-3-benzothiophene)-2-[2-methyl-5-(4-aminomethanephenyl)-3-thienyl]perfluorocyclopentene was written by Dong, Xiaorong;Wei, Shasha;Liu, Gang;Pu, Shouzhi. And the article was included in Advanced Materials Research (Durnten-Zurich, Switzerland) in 2014.HPLC of Formula: 10243-15-9 This article mentions the following:

A new unsym. photochromic diarylethene compound, 1-(2-methyl-3-benzothiophene)-2-[2-methyl-5-(4-aminomethanephenyl)]-3-thienyperfluorocyclopentene (I) was synthesized and its photochromic properties were examined The result indicated that the compound I changed the color from colorless to purple upon irradiation with 297 nm UV light, in which absorption maxima was observed at 564 nm in acetonitrile. The kinetic experiments showed that the cyclization and cycloreversion processes were zeroth and first order reactions, resp. This new photochromic system also exhibited fluorescence switching in acetonitrile solution In the experiment, the researchers used many compounds, for example, 3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9HPLC of Formula: 10243-15-9).

3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9) 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: 10243-15-9

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Modulation of the absorption, fluorescence, and liquid-crystal properties of functionalized diarylethene derivatives was written by Frigoli, Michel;Mehl, Georg H.. And the article was included in Chemistry – A European Journal in 2004.Application In Synthesis of 6-Methoxybenzo[b]thiophene This article mentions the following:

Systematic variation of the mol. symmetry in a photochromic system based on a 1,2-bis(2-methylbenzo[b]thiophen-3-yl)hexafluorocyclopentene group, connected by decyl spacers to two cyanobiphenyl groups as mesogens, allows for a systematic investigation of the correlations between mol. shape and symmetry, electronic effects, photochromic conversion and liquid-crystalline properties. In the experiment, the researchers used many compounds, for example, 6-Methoxybenzo[b]thiophene (cas: 90560-10-4Application In Synthesis of 6-Methoxybenzo[b]thiophene).

6-Methoxybenzo[b]thiophene (cas: 90560-10-4) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The core structure is a part of various pharmaceutical substances and natural products. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.Application In Synthesis of 6-Methoxybenzo[b]thiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Nickel-catalyzed and Li-mediated regiospecific C-H arylation of benzothiophenes was written by Mohr, Yorck;Hisler, Gaelle;Grousset, Leonie;Roux, Yoann;Quadrelli, Elsje Alessandra;Wisser, Florian M.;Canivet, Jerome. And the article was included in Green Chemistry in 2020.Safety of 6-Methoxybenzo[b]thiophene This article mentions the following:

A nickel-based catalytic system for the regiospecific C2-H arylation of benzothiophenes with aryl iodides to afford 2-aryl benzothiophenes I [R¹ = H, 5-Me, 5-F, etc.; Ar = Ph, 4-FC₆H₄, 1-naphthyl, etc.] was established. NiCl₂(bpy) was used as a catalyst in combination with LiHMDS as a base in dioxane. The catalytic system was applicable to a variety of functionalized benzothiophenes, as well as other heteroarenes including thiophene, benzodithiophene, benzofuran and selenophene in combination with iodo aryl electrophiles. The role of LiHMDS as a uniquely potent base and a postulated mechanism were discussed. The applicability of this system was finally demonstrated for the synthesis of an intermediate of an active pharmaceutical ingredient. In the experiment, the researchers used many compounds, for example, 6-Methoxybenzo[b]thiophene (cas: 90560-10-4Safety of 6-Methoxybenzo[b]thiophene).

6-Methoxybenzo[b]thiophene (cas: 90560-10-4) 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. It has been used as a raw material for the synthesis of biologically active structures and is found in pharmaceuticals such as leukotriene synthesis inhibitors and antifungals, as well as in many natural products.Safety of 6-Methoxybenzo[b]thiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Cope rearrangements in the benzo[b]thiophene series was written by Sura, Tushar P.;MacDowell, Denis W. H.. And the article was included in Journal of Organic Chemistry in 1993.Application of 6287-82-7 This article mentions the following:

The inability to observe Cope rearrangement products at elevated temperatures for di-Et α-allyl-2-naphthalenemalonate and di-Et α-allyl-9-phenanthrenemalonate does not extend to analogous systems resulting from replacement of the aromatic units by 2- and 3-benzo[b]thiophene nuclei. Thermal rearrangement of di-Et α-allyl-3-benzo[b]thiophenemalonate at 215-255°C for 11 h gave the expected Cope rearrangement product di-Et 2-allyl-3-benzo[b]thiophenemalonate (8%) accompanied by trans- and cis-Et 2,3-dihydro-1-(ethoxycarbonyl)-1H-benzo[b]cyclopenta[d]thiopehen-2-acetate in 10% yield 5% yield, resp. The attempted structure verification of 2-allyl-3-benzo[b]thiophenemalonate by an independent route gave di-Et 2-(1-propenyl)-3-benzo[b]thiophenemalonate which when heated at 230-240°C for 18 h gave 1-carbethoxy-2-hydroxy-3-methyldibenzothiophene as a major product. Similar results were observed with 2-substituted analogs of di-Et α-allyl-3-benzo[b]thiophenemalonate, both di-Et 3-allyl-2-benzo[b]thiophenemalonate and Et 1,2-dihydro-3-(ethoxycarbonyl)-3H-benzo[b]cyclopenta[d]thiophene-2-acetate were formed. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Application of 6287-82-7).

2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7) 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. The different substitution patterns in these heterocycles offer new opportunities for drug discovery and other applications in materials science.Application of 6287-82-7

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem