5381-20-4

Usage

Uses

Used in Pharmaceutical Industry:
1-Benzothiophene-3-carbaldehyde is used as a starting material for the multi-step synthesis of anthra[2,3-b:7,6-b′]bis[1benzothiophenes (ABBTs), which are a class of organic compounds with potential applications in the development of new drugs and therapeutic agents.
Used in Organic Synthesis:
1-Benzothiophene-3-carbaldehyde is used as a key intermediate in the synthesis of various organic compounds, such as:
6-(N,N-dimethylamino)-2-(benzo[b]thiophen-3-yl)quinazolin-4-one: 1-Benzothiophene-3-carbaldehyde may have potential applications in the development of new pharmaceuticals or materials.
6-(pyrrolidin-1-yl)-2-(benzo[b]thiophen-3-yl)quinazolin-4-one: 1-Benzothiophene-3-carbaldehyde can be used in the synthesis of new organic materials or as a precursor for further chemical reactions.
(Z)-2-(benzo-[b]-thio-phen-3-yl-methyl-ene)-1-aza-bi-cyclo-[2.2.2]-octan-3-one: 1-Benzothiophene-3-carbaldehyde may be used in the development of new organic materials or as a building block for more complex organic molecules.

InChI:InChI=1/C9H6OS/c10-5-7-6-11-9-4-2-1-3-8(7)9/h1-6H

Upstream product

• 3216-47-5 3-chloromethylbenzothiophene 
• 100-97-0 hexamethylenetetramine 
• 917-54-4 methyllithium 
• 86051-32-3 ⁽¹⁾benzothieno(3,2-d)isoselenazole 
• 7342-82-7 3-Bromothianaphthene 
• 68-12-2 N,N-dimethyl-formamide 
• 50-00-0 formaldehyd 
• 95-15-8 Benzo[b]thiophene 
• 4885-02-3 Dichloromethyl methyl ether 
• 119072-55-8 tert-butylisonitrile 
• 5381-25-9 benzo[b]thiophene-3-carboxylic acid 
• 1207738-76-8 N-methoxy-N-methylbenzo[b]thiophene-3-carboxamide 
• 5381-24-8 benzo[b]thiophen-3-yl methanol 
• 24434-84-2 benzo[b]thiophene-3-carbonitrile 

Downstream Products

• 35523-49-0 4-benzo[b]thiophen-3-ylmethylene-2-phenyl-4H-oxazol-5-one 
• 5370-66-1 N-Methyl-4-(3-benzothienylethenyl)-pyridinium-iodid 
• 35523-50-3 4-benzo[b]thiophen-3-ylmethylene-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one 
• 5592-03-0 NSC108783 
• 4565-13-3 3-styrylbenzothiophene 
• 2050-68-2 4,4'-dichlorobiphenyl 
• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 693228-22-7 2-(4-methoxyphenyl)-1-benzothiophene-3-carbaldehyde 
• 581-80-6 4,4'-bis(trifluoromethyl)biphenyl 
• 693228-25-0 2-(4'-benzotrifluoride)-benzo[b]thiophene-3-carboxaldehyde 
• 1591-30-6 (1,1'-biphenyl)-4,4'-dicarbonitrile 
• 4341-02-0 biphenyl-2,2'-dicarbonitrile 
• 2436-96-6 1-nitro-2-(2-nitrophenyl)benzene 
• 39856-98-9 bromo-2 formyl-3 <1>benzothiophene 

Relevant academic research and scientific papers

Unified Synthesis of Polycyclic Alkaloids by Complementary Carbonyl Activation**

A complementary dual carbonyl activation strategy for the synthesis of polycyclic alkaloids has been developed. Successful applications include the synthesis of tetracyclic alkaloids harmalanine and harmalacinine, pentacyclic indoloquinolizidine alkaloid nortetoyobyrine, and octacyclic β-carboline alkaloid peganumine A. The latter synthesis features a protecting-group-free assembly and an asymmetric disulfonimide-catalyzed cyclization. Furthermore, formal syntheses of hirsutine, deplancheine, 10-desbromoarborescidine A, and oxindole alkaloids rhynchophylline and isorhynchophylline have been achieved. Finally, a concise synthesis of berberine alkaloid ilicifoline B was completed.

Potent Inhibition of Nicotinamide N-Methyltransferase by Alkene-Linked Bisubstrate Mimics Bearing Electron Deficient Aromatics

Nicotinamide N-methyltransferase (NNMT) methylates nicotinamide (vitamin B3) to generate 1-methylnicotinamide (MNA). NNMT overexpression has been linked to a variety of diseases, most prominently human cancers, indicating its potential as a therapeutic target. The development of small-molecule NNMT inhibitors has gained interest in recent years, with the most potent inhibitors sharing structural features based on elements of the nicotinamide substrate and the S-adenosyl-l-methionine (SAM) cofactor. We here report the development of new bisubstrate inhibitors that include electron-deficient aromatic groups to mimic the nicotinamide moiety. In addition, a trans-alkene linker was found to be optimal for connecting the substrate and cofactor mimics in these inhibitors. The most potent NNMT inhibitor identified exhibits an IC50 value of 3.7 nM, placing it among the most active NNMT inhibitors reported to date. Complementary analytical techniques, modeling studies, and cell-based assays provide insights into the binding mode, affinity, and selectivity of these inhibitors.

Controlled Reduction of Nitriles by Sodium Hydride and Zinc Chloride

A new protocol for the controlled reduction of nitriles to aldehydes was developed using a combination of sodium hydride and zinc chloride. The iminyl zinc intermediates derived from aromatic nitriles could be further functionalized with allylmetal nucleophiles to afford homoallylamines. As the method allows the reduction of various aliphatic and aromatic nitriles with a concise procedure under milder reaction conditions and exhibits wide functional group compatibility, it is well suited for use in various opportunities in chemical synthesis.

Facile One-Pot Transformation of Primary Alcohols into 3-Aryl- and 3-Alkyl-isoxazoles and -pyrazoles

Various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylisoxazoles in good yields in one pot by successive treatment with PhI(OAc) 2 in the presence of TEMPO, NH 2 OH, and then NCS, followed by reaction with alkynes in the presence of Et 3 N. Similarly, various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylpyrazoles in good yields in one pot by successive treatment with PhI(OAc) 2 in the presence of TEMPO, PhNHNH 2, and then NCS and decyl methyl sulfide, followed by reaction with alkynes in the presence of Et 3 N. Thus, both 3-aryl- and 3-alkylisoxazoles, and 3-aryl- and 3-alkylpyrazoles could be prepared from readily available primary alcohols in one pot under transition-metal-free conditions.

PPAR (peroxisome proliferator-activated receptor) agonist and application thereof to treatment of senile dementia and other diseases

The invention relates to a compound, namely a gamma-subtype peroxisome proliferator-activated receptor (PPAR) agonist. In addition, the invention discloses a medicinal component and a preparation containing the compound and application of such the gamma-subtype PPAR agonist.

Visible light photocatalysis with CBr4: A highly selective aerobic photooxidation of methylarenes to aldehydes

A metal-free, operationally simple and efficient means of aerobic photooxidation of methylarenes to aromatic aldehydes at room temperature employing visible light photocatalysis with CBr4 is reported. The reaction is highly selective as it proceeds without any over oxidation to carboxylic acids. The utilisation of visible light and molecular oxygen is inexpensive, readily available, non-toxic and the sustainable reagents make the protocol compatible with green chemistry demands. A plausible mechanism for the formation of aldehydes from methylarenes is also provided.

Palladium-catalyzed synthesis of aldehydes from aryl halides and tert-butyl isocyanide using formate salts as hydride donors

An efficient one-pot palladium-catalyzed hydroformylation of aryl halides to produce aromatic aldehydes has been achieved, employing tert-butyl isocyanide as a C1 resource and formate salt as a hydride donor without any additional bases. Characterized by its mild reaction conditions, easy operation and lower toxicity, this reaction can tolerate a wide array of functional groups with moderate to excellent yields.

Palladium-catalyzed formylation of aryl halides with tert -butyl isocyanide

A novel palladium-catalyzed formylation of aryl halides with isocyanide in the presence of Et3SiH has been demonstrated, which provides a strategy toward important aldehydes with moderate to excellent yield. The advantage of this reaction includes milder conditions, convenient operation, lower toxicity, and wide functional group tolerance.

One-pot transformation of methylarenes into aromatic aldehydes under metal-free conditions

On the basis of studies of the transformation of benzylic bromides into the corresponding aromatic aldehydes by treatment with N-methylmorpholine N-oxide, various methylarenes were treated either with DBDMH in the presence of AIBN in acetonitrile at reflux (Method A) or with NBS in CCl4 under irradiation with a tungsten lamp at 30 °C (Method B), followed by treatment with N-methylmorpholine N-oxide to provide aromatic aldehydes in good yields. These methods could be adopted in one-pot transformations of methylarenes into aromatic aldehydes under conditions free of less toxic reagents and transition metals. Copyright

Enantioselective straightforward access to benzo[b]thiophene analogs of Azatoxin

Horner-Wadsworth Emmons olefination followed by asymmetric hydrogenation allowed the first synthetic access to the chiral thiotryptophan with good enantiomeric excess. Oxazolidinone formation followed by a Pictet-Spengler condensation provided the benzothiophenic analog of Azatoxin.