Heterocyclic Building Blocks-Benzothiophene

Wang, Zheng; Lin, Qing; Ma, Ning; Liu, Song; Han, Mingyang; Yan, Xiuli; Liu, Qingbin; Solan, Gregory A.; Sun, Wen-Hua published their research in Catalysis Science & Technology in 2021. The article was titled 《Direct synthesis of ring-fused quinolines and pyridines catalyzed by NNHY-ligated manganese complexes (Y = NR2 or SR)》.HPLC of Formula: 88-15-3 The article contains the following contents:

Four cationic manganese(I) complexes, [(fac-NNHN)Mn(CO)3]Br (Mn-1-Mn-3) and [(fac-NNHS)Mn(CO)3]Br (Mn-4) (where NNH is a 5,6,7,8-tetrahydro-8-quinolinamine moiety), have been synthesized and evaluated as catalysts for the direct synthesis of quinolines and pyridines by the reaction of a γ-amino alc. with a ketone or secondary alc.; NNHS-ligated Mn-4 proved the most effective of the four catalysts. The reactions proceeded well in the presence of catalyst loadings in the range 0.5-5.0 mol% and tolerated diverse functional groups such as alkyl, cycloalkyl, alkoxy, chloride and hetero-aryl. A mechanism involving acceptorless dehydrogenation coupling (ADC) has been proposed on the basis of DFT calculations and exptl. evidence. Significantly, this manganese-based catalytic protocol provides a promising green and environmentally friendly route to a wide range of synthetically important substituted monocyclic, bicyclic as well as tricyclic N-heterocycles (including 50 quinoline and 26 pyridine examples) with isolated yields of up to 93%. In addition to this study using 1-Thiophen-2-yl-ethanone, there are many other studies that have used 1-Thiophen-2-yl-ethanone(cas: 88-15-3HPLC of Formula: 88-15-3) was used in this study.

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Specialized thiophenes can be synthesized similarly using Lawesson’s reagent as the sulfidizing agent, or via the Gewald reaction, which involves the condensation of two esters in the presence of elemental sulfur. Another method is the Volhard–Erdmann cyclization. HPLC of Formula: 88-15-3

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

《The synthesis of fluorescent benzofuro[2,3-c]pyridines via palladium-catalyzed heteroaromatic C-H addition and sequential tandem cyclization》 was published in Organic Chemistry Frontiers in 2020. These research results belong to Xiong, Wenzhang; Chen, Zhongyan; Shao, Yinlin; Li, Renhao; Hu, Kun; Chen, Jiuxi. Application In Synthesis of 1-Thiophen-2-yl-ethanone The article mentions the following:

A Pd-catalyzed tandem reaction of 2-(cyanomethoxy)chalcones with thiophenes/2-methylfuran/1-methylpyrrole/1,2-dimethylindole through direct C-H addition and sequential intramol. conjugate addition/cyclization/aromatization provided a diverse range of 3-aryl-benzofuro[2,3-c]pyridines I [R = H, 6-Me, 6-MeO, 6-F, 6-Cl, 6-Br; R1 = 2-thienyl, 5-methyl-2-furyl, 1-methylpyrrol-2-yl, 1,2-dimethylindol-3-yl; Ar = Ph, 2-thienyl, 2-MeC6H4, etc.]. A representative product was assessed as a ratiometric fluorescent probe for Hg2+. In addition to this study using 1-Thiophen-2-yl-ethanone, there are many other studies that have used 1-Thiophen-2-yl-ethanone(cas: 88-15-3Application In Synthesis of 1-Thiophen-2-yl-ethanone) was used in this study.

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Specialized thiophenes can be synthesized similarly using Lawesson’s reagent as the sulfidizing agent, or via the Gewald reaction, which involves the condensation of two esters in the presence of elemental sulfur. Another method is the Volhard–Erdmann cyclization. Application In Synthesis of 1-Thiophen-2-yl-ethanone

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

《Comparison of acrylamide and furan concentrations, antioxidant activities, and volatile profiles in cold or hot brew coffees》 was published in Food Science and Biotechnology in 2020. These research results belong to Kang, Da-eun; Lee, Haeng-Un; Davaatseren, Munkhtugs; Chung, Myung-Sub. Category: benzothiophene The article mentions the following:

The aim of this study was to investigate the formation of furan and acrylamide and to compare antioxidant capacities and volatile compounds in cold or hot brewed coffees. Cold brews were prepared at 5°C and 20°C for 12 h. using steeping and dripping, and hot brews were prepared at 80°C and 95°C for 5 min. using the pour-over method. Furan contents of cold steeping at 5°C and hot brewed at 80°C showed the higher levels significantly (p < 0.05), which were 17.0 ± 0.5 and 10.6 ± 0.1 ng/mL, resp. However, acrylamide contents in cold steeping at 5°C and hot brew at 80°C showed lower levels, which were 4.1 ± 0.4 and 3.5 ± 0.1 ng/mL resp. Cold brews at 20°C showed the highest levels of antioxidant activities while hot brews showed similar levels with cold brews at 5°C. This study confirms that levels of different beneficial and hazardous chem. compounds could be manipulated by adjusting the coffee extraction conditions. In the experimental materials used by the author, we found 1-Thiophen-2-yl-ethanone(cas: 88-15-3Category: benzothiophene)

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Specialized thiophenes can be synthesized similarly using Lawesson’s reagent as the sulfidizing agent, or via the Gewald reaction, which involves the condensation of two esters in the presence of elemental sulfur. Another method is the Volhard–Erdmann cyclization. Category: benzothiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

《Enhanced Two-Photon Absorption of Cross-Conjugated Chalcone Derivatives: Modulation of the Effective π-Conjugated Structure》 was written by Jia, Jidong; Zhang, Xueru; Wang, Yuxiao; Shi, Yufang; Sun, Jinyu; Yang, Junyi; Song, Yinglin. Formula: C6H6OS And the article was included in Journal of Physical Chemistry A in 2020. The article conveys some information:

Three cross-conjugated chalcone derivatives T3CT, T3CP2, and T3CP3 were designed and synthesized to develop excellent organic nonlinear optical (NLO) materials. In a Z-scan experiment, all compounds show good NLO absorption characteristics in the visible to near-IR region. The photophys. mechanism is confirmed to be two-photon absorption (TPA)-induced excited-state absorption (ESA). Intramol. charge transfer (ICT) observed in transient absorption spectra (TAS) significantly affects mol. NLO properties. We define the π-conjugated system that dominates the electron transition process in the cross-conjugated structure as the effective π-conjugated structure. Electron transition anal. shows a sufficiently strong ICT can effectively expand the effective π-conjugated structure in these cross-conjugated structures. The TPA cross sections of these compounds at 650 and 750 nm are only in the range of 17-97 GM. However, we achieve a significant enhancement of the TPA cross section at 580 nm (1737-2027 GM) by extending the effective π-conjugated structure. Excited by 580 nm femtosecond laser pulses, all compounds exhibit excellent OL performance and the min. OL threshold is 4.71 x 10-3 J/cm2. The results show that these cross-conjugated chalcone derivatives have promising applications in OL, and their NLO performance can be effectively improved by modulating the effective π-conjugated structure. The results came from multiple reactions, including the reaction of 1-Thiophen-2-yl-ethanone(cas: 88-15-3Formula: C6H6OS)

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Specialized thiophenes can be synthesized similarly using Lawesson’s reagent as the sulfidizing agent, or via the Gewald reaction, which involves the condensation of two esters in the presence of elemental sulfur. Another method is the Volhard–Erdmann cyclization. Formula: C6H6OS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

《NH4OAc-Promoted Domino Route to Hydroxyarylated Unsymmetrical Pyridines under Neat Conditions》 was written by Prakash, Meher; Gudimella, Santosh K.; Lodhi, Rajni; Guin, Soumitra; Samanta, Sampak. COA of Formula: C6H6OS And the article was included in Journal of Organic Chemistry in 2020. The article conveys some information:

A new metal-, oxidant-, and solvent-free ecofriendly domino method has been established for modular synthesis of a diverse range of medicinally promising hydroxyarylated unsym. pyridines in good to high chem. yields with an excellent regioselectivity. This domino process involves a range of N-sulfonyl ketimines as C,N-binucleophiles, enolizable ketones, and aromatic/heteroaromatic aldehydes using ammonium acetate as an ideal promoter under neat conditions, which creates two new C-C bonds and one C-N bond. Notably, the neutral reaction conditions are mild enough to tolerate a range of functionalities and cover a variety of substrates, thus bestowing a powerful avenue to access tri- and tetrasubstituted pyridines including carbo- and heterocyclic fused ones. Interestingly, a practical, scalable, and high-yielding synthesis of pyridylphenol derivatives was successfully accomplished by our unique method. In the experiment, the researchers used many compounds, for example, 1-Thiophen-2-yl-ethanone(cas: 88-15-3COA of Formula: C6H6OS)

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Specialized thiophenes can be synthesized similarly using Lawesson’s reagent as the sulfidizing agent, or via the Gewald reaction, which involves the condensation of two esters in the presence of elemental sulfur. Another method is the Volhard–Erdmann cyclization. COA of Formula: C6H6OS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

《Iodide-Selective PVC Membrane Electrode Based on Copper Complex of 2-Acetylthiophene Semicarbazone as Carrier》 was written by Suman, Shankar; Singh, Ram. Formula: C6H6OS And the article was included in Analytical Chemistry Letters in 2020. The article conveys some information:

A highly selective poly(vinyl chloride) (PVC) membrane electrode based on copper (II) complex of 2 acetylthiophene semicarbazone as a new carrier for iodide selective electrode is fabricated with the composition of PVC (30%), plasticizer (64%), ionophore (4%) and lipophilic additive (2%). The prepared electrode has been found to exhibit the best sensitivity over a wide concentration range of 1×10-6 to 3.2×10-2 M with a near Nernstian response of 57.2 mV per decade over a wide pH range of 2.5 10.5. The detection limit for the electrode was found to be 5.50×10-7 M with the response time of 15 s and can be used for at least 3 mo without any considerable divergence in its potential response. In addition to this study using 1-Thiophen-2-yl-ethanone, there are many other studies that have used 1-Thiophen-2-yl-ethanone(cas: 88-15-3Formula: C6H6OS) was used in this study.

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Specialized thiophenes can be synthesized similarly using Lawesson’s reagent as the sulfidizing agent, or via the Gewald reaction, which involves the condensation of two esters in the presence of elemental sulfur. Another method is the Volhard–Erdmann cyclization. Formula: C6H6OS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

《Synthesis, single crystal structure, DNA binding and antioxidant properties of 5-(4-(dimethylamino)phenyl)-3-(thiophen-2-yl)-pyrazoline-1-carbothioamide》 was written by Rana, Manish; Fatima, Aysha; Siddiqui, Nazia; Dar, Sajad Hussain; Javed, Saleem; Rahisuddin. Reference of 1-Thiophen-2-yl-ethanoneThis research focused onthiophenyl pyrazoline carbothioamide preparation crystal structure DNA binding antioxidant. The article conveys some information:

5-(4-(Dimethylamino)phenyl)-3-(thiophen-2-yl)-pyrazoline-1-carbothioamide I was synthesized. The compound shows strong antioxidant activity with IC50 value of 0.632 ± 0.002μg/mL. The compound crystallizes as a monoclinic system, P21/c centro-sym. space group, Z = 8 and size of the corresponding unit cell: a = 11.7134(10) Å , b = 17.3334(15) Å , c = 16.9831(14) Å , α = 90, β = 108.038(2), γ = 90. DNA binding measurements (UV-vis., fluorescence, cyclic voltammetry and competitive assay using ethidium bromide) of compounds showed intercalative mode of interaction. The binding constant (Kb), Gibbs free energy (ΔG) of compound I were found to be 1.3 x 105 M-1 and -67.17 KJmol-1, resp. The calculated Ksv values at two different temperatures (298 and 303 K) are 3.02 x 103 and 2.16 x 103 M-1 resp. To optimize mol. structure and compute wavenumbers of normal vibrational modes, B3LYP method and 6-311 ++ G (d, p) basis set were used. Hirshfeld surface anal. provides a thorough illustration of the intermol. interactions on crystal surface, and fingerprint plots were discovered. Exptl. bond lengths and bond angles corroborated well with the computational parameters. The GIAO approach was used to estimate 1H-NMR and 13C-NMR chem. shifts, and compared to exptl. spectra. Electronic properties such as UV-Vis (in gas phase, ethanol and DMSO) were analyzed using TD-DFT method and the PCM solvent model, and results were compared to exptl. UV-Vis spectra. In the part of experimental materials, we found many familiar compounds, such as 1-Thiophen-2-yl-ethanone(cas: 88-15-3Reference of 1-Thiophen-2-yl-ethanone)

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Reflecting their high stabilities, thiophenes arise from many reactions involving sulfur sources and hydrocarbons, especially unsaturated ones. Thiophenes are classically prepared by the reaction of 1,4-diketones, diesters, or dicarboxylates with sulfidizing reagents such as P4S10 such as in the Paal-Knorr thiophene synthesis. Reference of 1-Thiophen-2-yl-ethanone

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

《Palladium-carbene catalyzed direct arylation of five-membered heteroaromatics》 was written by Kaloglu, Murat; Kaloglu, Nazan; Yildirim, Ilkay; Ozdemir, Namik; Ozdemir, Ismail. Computed Properties of C6H6OS And the article was included in Journal of Molecular Structure in 2020. The article conveys some information:

In this study, PEPPSI-type, (PEPPSI = Pyridine Enhanced Precatalyst Preparation Stabilization and Initiation), new Pd-catalysts with N-heterocyclic carbene ligand I [R1 = Ph, 4-MeC6H4, 2,4,6-(Me)3C6H2, etc.; R2 = nBu, 3-MeOC6H4; X = Cl, Br] were synthesized and used as catalysts in the synthesis of bi(hetero)arenes R3-R4 [R3 = 5-acetyl-2-thienyl, furan-2-carbonyl, 4,5-dimethyl-thiazolyl; R4 = Ph, 4-MeC6H4, 3-quinolyl, etc.] by direct arylation process. The structures of complexes I were elucidated by different spectroscopic and anal. techniques such as NMR, FT-IR and elemental anal. The more detailed structural characterization of one of the complexes I [R1 = 4-MeC6H4; R2 = 3-MeOC6H4; X = Br] was determined by single-crystal X-ray diffraction study. Complexes I were used as effective catalysts in the direct arylation of five-membered heteroaromatics such as thiophene, furan and thiazole derivatives with aryl bromides in the presence of 1 mol% of catalyst loading and successful results were obtained. In the experimental materials used by the author, we found 1-Thiophen-2-yl-ethanone(cas: 88-15-3Computed Properties of C6H6OS)

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Reflecting their high stabilities, thiophenes arise from many reactions involving sulfur sources and hydrocarbons, especially unsaturated ones. Thiophenes are classically prepared by the reaction of 1,4-diketones, diesters, or dicarboxylates with sulfidizing reagents such as P4S10 such as in the Paal-Knorr thiophene synthesis. Computed Properties of C6H6OS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

The author of 《Lewis Base-Catalyzed Enantioselective Conjugate Reduction of β,β-Disubstituted α,β-Unsaturated Ketones with Trichlorosilane: E/Z-Isomerization, Regioselectivity, and Synthetic Applications》 were Sugiura, Masaharu; Ashikari, Yasuhiko; Takahashi, Yuka; Yamaguchi, Koki; Kotani, Shunsuke; Nakajima, Makoto. And the article was published in Journal of Organic Chemistry in 2019. Synthetic Route of C6H6OS The author mentioned the following in the article:

The chiral bisphosphine dioxide-catalyzed asym. conjugate reduction of acyclic β,β-disubstituted α,β-unsaturated ketones with trichlorosilane affords saturated ketones having a stereogenic carbon center at the carbonyl β-position with high enantioselectivities. Because the E/Z-isomerizations of enone substrates occur concomitantly, reduction products with the same absolute configurations are obtained from either (E)- or (Z)-enones. Conjugate reduction is accelerated in the presence of an electron-rich aryl group at the β-position of the enone owing to its carbocation-stabilizing ability. Computational studies were also conducted in order to elucidate the origin of the observed enantioselectivity. The regio- and enantioselective reductions of dienones were realized and applied to the syntheses of ar-turmerone, turmeronol A, mutisianthol, and jungianol, which are optically active sesquiterpenes. The experimental process involved the reaction of 1-Thiophen-2-yl-ethanone(cas: 88-15-3Synthetic Route of C6H6OS)

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Reflecting their high stabilities, thiophenes arise from many reactions involving sulfur sources and hydrocarbons, especially unsaturated ones. Thiophenes are classically prepared by the reaction of 1,4-diketones, diesters, or dicarboxylates with sulfidizing reagents such as P4S10 such as in the Paal-Knorr thiophene synthesis. Synthetic Route of C6H6OS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

《Preparation of optically active 2-(or 3)(p-tolylsulfinyl)-3(or 2)furyl- or thienylcarboxaldehydes》 was written by Girodier, Laurent D.; Maignan, Christian S.; Rouessac, Francis P.. Application In Synthesis of 2-(Thiophen-3-yl)-1,3-dioxolane And the article was included in Tetrahedron: Asymmetry on August 31 ,1995. The article conveys some information:

The preparation of the four enantiomerically pure title compounds is described by reaction of (1)-(-)-Ss-menthyl-p-toluenesulfinate on furan or thiophene precursors. The experimental process involved the reaction of 2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3Application In Synthesis of 2-(Thiophen-3-yl)-1,3-dioxolane)

2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3) is one of dioxolane. 1,3-Dioxolane derivatives are recognized as important motifs for the construction of numerous pharmacologically active molecules as antiviral, antifungal, anti-HIV, and adrenoreceptor antagonists.Application In Synthesis of 2-(Thiophen-3-yl)-1,3-dioxolane

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem