Heterocyclic Building Blocks-Benzothiophene

《The development of a one pot, regiocontrolled, three-component reaction for the synthesis of thieno[2,3-c]pyrroles》 was published in Organic & Biomolecular Chemistry in 2013. These research results belong to Hong, Cynthia M.; Statsyuk, Alexander V.. Category: benzothiophene The article mentions the following:

A three-component reaction has been developed that allows the regioselective synthesis of thieno[2,3-c]pyrroles, e.g. I. The reaction is based on the ability of 2-acetyl-3-thiophenecarboxaldehyde to react with amine and thiol nucleophiles to produce the corresponding tri-substituted thieno[2,3-c]pyrroles, with water as the only byproduct. The developed reaction expands the range of synthetically accessible, tri-substituted thieno[2,3-c]pyrroles. In the experimental materials used by the author, we found 2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3Category: benzothiophene)

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.Category: benzothiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

In 2019,Angewandte Chemie, International Edition included an article by Zhang, Linli; Tang, Yitian; Han, Zhaobin; Ding, Kuiling. Synthetic Route of C6H6OS. The article was titled 《Lutidine-Based Chiral Pincer Manganese Catalysts for Enantioselective Hydrogenation of Ketones》. The information in the text is summarized as follows:

A series of MnI complexes containing lutidine-based chiral pincer ligands (S,S) or (R,R) I (R = H, Me, t-Bu, Cl, OMe; R1 = i-Pr, Bn) with modular and tunable structures has been developed. The complex shows unprecedentedly high activities (up to 9800 TON; TON = turnover number), broad substrate scope (81 examples), good functional-group tolerance, and excellent enantioselectivities (85-98% ee) in the hydrogenation of various ketones, e.g., acetophenone. These aspects are rare in earth-abundant metal catalyzed hydrogenations. The utility of the protocol have been demonstrated in the asym. synthesis of a variety of key intermediates for chiral drugs. Preliminary mechanistic investigations indicate that an outer-sphere mode of substrate-catalyst interactions probably dominates the catalysis.1-Thiophen-2-yl-ethanone(cas: 88-15-3Synthetic Route of 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. Synthetic Route of C6H6OS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

In 2019,Journal of the American Chemical Society included an article by Zhu, Xiaotao; Deng, Weili; Chiou, Mong-Feng; Ye, Changqing; Jian, Wujun; Zeng, Yuehua; Jiao, Yihang; Ge, Liang; Li, Yajun; Zhang, Xinhao; Bao, Hongli. HPLC of Formula: 88-15-3. The article was titled 《Copper-catalyzed radical 1,4-difunctionalization of 1,3-enynes with alkyl diacyl peroxides and N-fluorobenzenesulfonimide》. The information in the text is summarized as follows:

Many reactions involving allenyl ion species have been studied, but reactions involving allenyl radicals are less well understood, perhaps because of the inconvenience associated with the generation of short-lived allenyl radicals. We describe here a versatile method for the generation of allenyl radicals and their previously unreported applications in the intermol. 1,4-carbocyanation and 1,4-sulfimidocyanation of 1,3-enynes. With the assistance of the trifunctional reagents, alkyl diacyl peroxides or N-fluorobenzenesulfonimide, a range of synthetically challenging multi-substituted allenes can be prepared with high regioselectivity. These multi-substituted allenes can be easily transformed into synthetically useful structures such as fluorinated vinyl cyanides, lactones, functionalized allenyl amides, 1-aminonaphthalenes, and pyridin-2(1H)-ones, and several novel transformations are reported. The results of radical scavenger and radical clock experiments are consistent with the proposed allenyl radical pathway. D. functional theory (DFT) and IR spectroscopy studies suggest the formation of an isocyanocopper(II) species in the ligand exchange step. On the basis of the results of IR, DFT, and diastereoselectivity studies, an isocyanocopper(II)/copper(I) catalytic cycle is proposed, which differs from the previously considered Cu(III) mechanism in cyanation reactions. In the part of experimental materials, we found many familiar compounds, such as 1-Thiophen-2-yl-ethanone(cas: 88-15-3HPLC of Formula: 88-15-3)

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 author of 《Photocatalytic decarboxylative alkylations mediated by triphenylphosphine and sodium iodide》 were Fu, Ming-Chen; Shang, Rui; Zhao, Bin; Wang, Bing; Fu, Yao. And the article was published in Science (Washington, DC, United States) in 2019. Formula: C6H6OS The author mentioned the following in the article:

Most photoredox catalysts in current use are precious metal complexes or synthetically elaborate organic dyes, the cost of which can impede their application for large-scale industrial processes. We found that a combination of triphenylphosphine and sodium iodide under 456-nm irradiation by blue light-emitting diodes can catalyze the alkylation of silyl enol ethers by decarboxylative coupling with redox-active esters in the absence of transition metals. Deaminative alkylation using Katritzky’s N-alkylpyridinium salts and trifluoromethylation using Togni’s reagent are also demonstrated. Moreover, the phosphine/iodide-based photoredox system catalyzes Minisci-type alkylation of N-heterocycles and can operate in tandem with chiral phosphoric acids to achieve high enantioselectivity in this reaction. In the experiment, the researchers used many compounds, for example, 1-Thiophen-2-yl-ethanone(cas: 88-15-3Formula: 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. Formula: C6H6OS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

In 2022,Akolkar, Hemantkumar N.; Dengale, Sujata G.; Deshmukh, Keshav K.; Karale, Bhausaheb K.; Darekar, Nirmala R.; Khedkar, Vijay M.; Shaikh, Mubarak H. published an article in Polycyclic Aromatic Compounds. The title of the article was 《Design, Synthesis and Biological Evaluation of Novel Furan and Thiophene Containing Pyrazolyl Pyrazolines as Antimalarial Agents》.Product Details of 88-15-3 The author mentioned the following in the article:

In search for novel compounds targeting malaria, based on the in silico mol. docking binding affinity data, the novel furans containing pyrazolyl chalcones I (R = H, 4-F; Ar = Ph, thiophen-2-yl, 5-bromothiophen-2-yl) and pyrazoline derivatives II were synthesized. Compounds with thiophene and pyrazoline ring II (R = 4-F; Ar = 5-bromothiophen-2-yl) (0.47μM), II (R = H; Ar = 5-bromothiophen-2-yl) (0.47μM) and II (R = H; Ar = thiophen-2-yl) (0.21μM) exhibited excellent anti-malarial activity against Plasmodium falciparum compared with standard antimalarial drug quinine (0.83μM). To check the selectivity furthermore, compounds were tested for antimicrobial activity and none of the synthesized compound exhibited significant potency compared with the standard antibacterial drug chloramphenicol and antifungal drug nystatin resp. So, it can be resolved that the synthesized compounds show selectively antimalarial activity and have the potential to be explored further. In the part of experimental materials, we found many familiar compounds, such as 1-Thiophen-2-yl-ethanone(cas: 88-15-3Product Details of 88-15-3)

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. Product Details of 88-15-3

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

HPLC of Formula: 88-15-3In 2022 ,《Determination of the semiexperimental equilibrium structure of 2-acetylthiophene in the presence of methyl internal rotation and substituent effects compared to thiophene》 was published in Physical Chemistry Chemical Physics. The article was written by Dindic, Christina; Ludovicy, Jil; Terzi, Vladimir; Luechow, Arne; Vogt, Natalja; Demaison, Jean; Nguyen, Ha Vinh Lam. The article contains the following contents:

The microwave spectra of thiophene and 2-acetylthiophene were recorded in the frequency range from 2 to 40 GHz using two mol. jet Fourier transform microwave spectrometers. For 2-acetylthiophene, two conformers with a syn and an anti orientation of the S1-C2 and C6=O bonds (with respect to the C2-C6 bond) were identified, and the syn-conformer was more stable. The spectra of the 34S- and 13C-isotopologues of syn-2-acetylthiophene were also assigned, and the semiexperimental equilibrium structure could be determined Compared to thiophene, at the substitution position, the S1-C2 and C2C3 bond lengths both increase by about 0.007 Å, and the bond angle S1-C2C3 decreases by 0.06°, noticeably larger than the exptl. uncertainties. A-E torsional splittings were observed due to internal rotation of the Me group hindered by a barrier height of 330.187(35) and 295.957(17) cm-1 for the syn-conformer and the anti-conformer, resp. Geometry and internal rotation parameters are compared with those of related thiophene derivatives, as well as those of furan and 2-acetylthiophene to gain a better understanding of structure determination in the presence of Me internal rotation. The results came from multiple reactions, including the reaction of 1-Thiophen-2-yl-ethanone(cas: 88-15-3HPLC of Formula: 88-15-3)

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. HPLC of Formula: 88-15-3

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

In 2019,Journal of Heterocyclic Chemistry included an article by Shelke, Premchand B.; Mali, Suraj N.; Chaudhari, Hemchandra K.; Pratap, Amit P.. Application In Synthesis of 1-Thiophen-2-yl-ethanone. The article was titled 《Chitosan hydrochloride mediated efficient, green catalysis for the synthesis of perimidine derivatives》. The information in the text is summarized as follows:

Chitosan hydrochloride as biopolymer-based, renewable and recyclable heterogeneous catalyst was used for efficient one-pot synthesis of 2,3-dihydro-1H-perimidine derivatives I [R1 = H, Me, Et, Ph; R2 = Me, Ph, 2-furyl, etc.; R1R2 = (CH2)5] via reaction of naphthalene-1,8-diamine with various ketones. This newly developed greener methodol. provided a very simple and greener route for the synthesis of perimidines in short time with excellent yield.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

Formula: C6H6OSIn 2019 ,《Catalytic Enantioselective Addition of Prochiral Radicals to Vinylpyridines》 appeared in Journal of the American Chemical Society. The author of the article were Cao, Kangning; Tan, Siu Min; Lee, Richmond; Yang, Songwei; Jia, Hongshao; Zhao, Xiaowei; Qiao, Baokun; Jiang, Zhiyong. The article conveys some information:

Pyridine, one of the most important azaarenes, is ubiquitous in functional mols. The electronic properties of pyridine were exploited to trigger asym. transformations of prochiral species as a direct approach for accessing chiral pyridine derivatives However, the full potential of this synthetic strategy for the construction of enantioenriched γ-functionalized pyridines remains untapped. Here, the authors describe the first enantioselective addition of prochiral radicals to vinylpyridines under cooperative photoredox and asym. catalysis mediated by visible light. The enantioselective reductive couplings of vinylpyridines with aldehydes, ketones, and imines were achieved by employing a chiral Bronsted acid to activate the reaction partners and provide stereocontrol via H-bonding interactions. Valuable chiral γ-secondary/tertiary hydroxyl- and amino-substituted pyridines were obtained in high yields with good to excellent enantioselectivities.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. 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. Formula: C6H6OS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

《Synthesis of 4,6-dihydrothieno[3,4-b]thiophene》 was published in Journal of Organic Chemistry in 1966. These research results belong to MacDowell, Denis W. H.; Patrick, Timothy B.. Recommanded Product: 13250-82-3 The article mentions the following:

The synthesis of the title compound (I) along with several new 2,3-disubstituted thiophenes is described. N.M.R. and uv spectra of I are discussed with respect to possible ring strain in the thiophene nucleus. The experimental process involved the reaction of 2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3Recommanded Product: 13250-82-3)

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.Recommanded Product: 13250-82-3

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Reference of 1-Thiophen-2-yl-ethanoneIn 2019 ,《Thiophene and furan appended pyrazoline based fluorescent chemosensors for detection of Al3+ ion》 was published in Inorganic Chemistry Communications. The article was written by Rangasamy, Manjunath; Palaninathan, Kannan. The article contains the following contents:

Thiophene and furan appended pyrazoline receptors R1 and R2 were designed and synthesized for selective detection of Al3+ ion. Their photophys. properties were studied by UV-visible and fluorescence spectra. Surprisingly, both receptors R1 and R2 were displayed an excellent selective and sensitive response to Al3+ ion alone over other tested metal ions. Both the receptor R1 and R2 displays 1:1 stoichiometry for [R1-Al3+] and [R2-Al3+] complex and formed with an association constant of 1.84 × 104 M-1 and 1.92 × 104 M-1 resp. The limit of detection were calculated for R1 and R2 since 8.92 × 10-8 M and 1.04 × 10-7 M by the fluorescence titration method. The thiophene based receptor R1 exhibited superior chemosensor characteristics such as high intensity absorption and emission at longer wavelength as compered that of furan based receptor R2. 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