17890-55-0

Usage

Synthesis Reference(s)

Synthetic Communications, 23, p. 743, 1993 DOI: 10.1080/00397919308009834Synthesis, p. 58, 1978

InChI:InChI=1/C11H10O2S/c1-2-13-11(12)10-7-8-5-3-4-6-9(8)14-10/h3-7H,2H2,1H3

Upstream product

• 55163-91-2 ethyl thioglycolate sodium salt 
• 89-98-5 2-chloro-benzaldehyde 
• 89407-29-4 (2-Formyl-phenylsulfanyl)-acetic acid ethyl ester 
• 623-51-8 ethyl 2-sulfanylacetate 
• 6630-33-7 ortho-bromobenzaldehyde 
• 552-89-6 2-nitro-benzaldehyde 
• 623-47-2 propynoic acid ethyl ester 
• 55164-16-4 2,2'-dithiodibenzaldehyde 
• 105-36-2 ethyl bromoacetate 
• 64-17-5 ethanol 
• 201230-82-2 carbon monoxide 
• 1191415-24-3 2-(2,2-dibromovinyl)benzenethiol 
• 95-15-8 Benzo[b]thiophene 
• 109-94-4 formic acid ethyl ester 

Downstream Products

• 17890-56-1 benzothiophene-2-methanol 
• 6314-28-9 benzo[b]thiophene-2-carboxylic acid 
• 30962-69-7 2-(β-Hydroxyethyl)-benzothiophene 
• 95-15-8 Benzo[b]thiophene 
• 175135-07-6 benzo[b]thiophene-2-carboxylic acid hydrazide 
• 10133-20-7 2-bromomethylbenzo[b]thiophene 
• 22720-75-8 2-acetyl benzo[b]thiophene 

Relevant academic research and scientific papers

Reaction of 2H-1-Benzothiete with Diazo Compounds in the Presence of Rhodium(II) Acetate

2,3-Dihydrobenzothiophenes (7a-e) were prepared by the Rh2+ catalyzed reaction of 2H-1-benzothiete (1) and diazo compounds (3a-e). α, β-Unsaturated diazo esters (3b,e) and diazo ketones (3d,e) yielded additionally 4,5-dihydro-1-benzothiepins

Practical synthesis of 2-acetylbenzo[b]thiophene

2-Acetyl-benzo[b]thiophene and its oxime were prepared from 2-nitrobenzaldehyde in good yields and under convenient conditions.

Heterocyclic compound for treating osteoporosis as well as preparation method and application of heterocyclic compound

The invention relates to the field of a medicine for preventing and treating osteoporosis. The invention provides a pyrazole heterocyclic compound or pharmaceutically acceptable salt of the compound. An in-vivo test finds out that the pyrazole heterocyclic compound can be used for inhibiting bone turnover rate enhancement and bone destruction, which are caused by ovariectomy; meanwhile, the concentration of blood calcium can be improved and deposition of bones is facilitated, so that the pyrazole heterocyclic compound has remarkable effects of preventing and treating the osteoporosis.

Accepting the Invitation to Open Innovation in Malaria Drug Discovery: Synthesis, Biological Evaluation, and Investigation on the Structure-Activity Relationships of Benzo[b]thiophene-2-carboxamides as Antimalarial Agents

Malaria eradication is a global health priority, but current therapies are not always suitable for providing a radical cure. Artemisinin has paved the way for the current malaria treatment, the so-called Artemisinin-based Combination Therapy (ACT). However, with the detection of resistance to ACT, innovative compounds active against multiple parasite species and at multiple life stages are needed. GlaxoSmithKline has recently disclosed the results of a phenotypic screening of an internal library, publishing a collection of 400 antimalarial chemotypes, termed the “Malaria Box”. After analysis of the data set, we have carried out a medicinal chemistry campaign in order to define the structure-activity relationships for one of the released compounds, which embodies a benzothiophene-2-carboxamide core. Thirty-five compounds were prepared, and a description of the structural features responsible for the in vitro activity against different strains of P. falciparum, the toxicity, and the metabolic stability is herein reported.

MODULATORS FOR NICOTINIC ACETYLCHOLINE RECEPTOR α2 AND α4 SUBUNITS

Positive allosteric modulators (PAMs) of nicotinic acetylcholine receptors (nAChR) are important therapeutic candidates as well as valuable research tools. We identified a novel type II PAM, (R)-7-bromo-N-(piperidin-3-yl)benzo[b]thiophene-2-carboxamide (B

Cu(ii)-catalyzed esterification reaction via aerobic oxidative cleavage of C(CO)-C(alkyl) bonds

A novel Cu(ii)-catalyzed aerobic oxidative esterification of simple ketones for the synthesis of esters has been developed with wide functional group tolerance. This process is assumed to go through a tandem sequence consisting of α-oxygenation/esterification/nucleophilic addition/C-C bond cleavage and carbon dioxide is released as the only byproduct.

A family of low molecular-weight, organic catalysts for reductive C-C bond formation

Hydrazines form a new family of low molecular-weight reducing agents for diazonium salts. Using only small amounts of hydrazine catalyst, the coupling of diazonium salts to a variety of reactive partners has been achieved, without the requirement for either metal adjuvants or irradiation with visible or ultraviolet light. The generality of the concept proposed herein as well as its advantages in the preparative scale is outlined and discussed.

Synthesis of a novel class of substituted benzothiophene or benzofuran derivatives as BMP-2 up-regulators and evaluation of the BMP-2-up-regulating effects in vitro and the effects on glucocorticoid-induced osteoporosis in rats

The BMP pathway is a promising new target for the design of therapeutic agents for the treatment of low bone mass. To enrich our understanding of SAR and based on our previously concluded structure-effect relationship, 23 derivatives were prepared in this

One-pot transformation of carboxylic acids into nitriles

A variety of aromatic and aliphatic carboxylic acids were smoothly converted into the corresponding nitriles in good yields in a one-pot procedure by treatment with ethyl iodide/K2CO3/18-crown-6, followed by sodium diisobutyl-tert-butoxyaluminium hydride (SDBBA-H), and finally treatment with molecular iodine or 1,3-diiodo-5,5-dimethylhydantoin (DIH), and aqueous ammonia. This method is useful for the conversion of various aromatic and aliphatic carboxylic acids into the corresponding nitriles in a one-pot procedure. A variety of aromatic and aliphatic carboxylic acids were smoothly converted into the corresponding nitriles in good yields in a one-pot procedure by treatment with ethyl iodide/K2CO3/18-crown-6, followed by sodium diisobutyl-tert-butoxyaluminium hydride (SDBBA-H), and finally treatment with molecular iodine or 1,3-diiodo-5,5-dimethylhydantoin (DIH), and aqueous ammonia. Copyright

An unusual 1,2-aryl shift in palladium-catalyzed cross-coupling ethoxycarbonylation of arylboronic acids with α-iminoesters

The Pd-catalyzed cross-coupling ethoxycarbonylation of aryl boronic acids with N-aryl-α-iminoesters affords aryl carboxylic esters via carbonyl-imino σ bond cleavage. This unprecedented mode of reaction allows regioselective installation of the ethoxycarbonyl group into target molecules. Mechanism studies have revealed that an unusual 1,2-aryl shift process is involved in the transformation. The Royal Society of Chemistry.