6622-22-6

Usage

Uses

Used in Pharmaceutical Industry:
(2Z)-2-(thiophen-2-ylmethylidene)-1-benzofuran-3(2H)-one is used as a potential pharmaceutical compound for its unique structure and properties. Its heterocyclic nature and the presence of both benzofuran and thiophene rings may contribute to its activity against various biological targets, warranting further research into its therapeutic potential.
Used in Organic Synthesis:
In the field of organic synthesis, (2Z)-2-(thiophen-2-ylmethylidene)-1-benzofuran-3(2H)-one can be utilized as a key intermediate or building block for the synthesis of more complex molecules. Its distinctive structure may facilitate the development of novel compounds with specific applications in various industries, including materials science, agrochemicals, and pharmaceuticals.

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 7169-34-8 3-oxo-2,3-dihydrobenzo[b]furan 
• 118-93-4 o-hydroxyacetophenone 
• 119271-85-1 3-(2-thienyl)-1-(2-hydroxyphenyl)-2-propen-1-one 
• 4298-52-6 2-ethynyl-thiophene 
• 533-58-4 2-Iodophenol 
• 201230-82-2 carbon monoxide 

Downstream Products

• 1510838-47-7 2-phenyl-4-(thiophen-2-yl)benzofuro[3,2-b]pyridine 

Relevant academic research and scientific papers

Vinylcyclopropanes as All-Carbon 1,5-Dipoles: A Reactivity Switch for Palladium-Catalyzed (5 + 4) Cycloadditions

Azonanes were prepared by a palladium-catalyzed (5 + 4) cycloaddition between activated vinylcyclopropanes and 1-azadienes. During this process, the vinylcyclopropane partner displayed an unusual reactivity and behaved as an all-carbon 1,5-dipole. A N,N-bidentate ligand was required to inhibit the formation of thermodynamic (3 + 2) cycloadducts.

A Palladium-Catalyzed Oxa-(4+4)-Cycloaddition Strategy towards Oxazocine Scaffolds

A Pd-catalyzed oxa-(4+4)-cycloaddition between 1-azadienes and (2-hydroxymethyl)allyl carbonates is described. Aurone-derived azadienes furnished polycyclic 1,5-oxazocines in good yields. Interestingly, linear azadienes have also been involved and yielded monocyclic heterocycles with complete regioselectivity. DFT calculations were carried out to gain insight on this observation.

Diversity-oriented synthesis of benzofuro[3,2-b]pyridine derivatives from aurone-derived α,β-unsaturated imines and activated terminal alkynes

An efficient annulation reaction of aurone-derived α,β-unsaturated imines and activated terminal alkynes mediated by triethylamine is described, which enables the facile synthesis of 1,4-dihydrobenzofuro[3,2-b]pyridines in high yields. When the nucleophil

Divergent synthesis of flavones and aurones via base-controlled regioselective palladium catalyzed carbonylative cyclization

A regioselective approach for construction of 5-membered and 6-membered flavonoid is established by Pd catalyzed carbonylative cyclization of 2-iodophenol with terminal alkynes using different amine bases under mild reaction condition. The catalytic experiments found that piperazine preferentially accelerate 6-endo cyclization, and triethylamine mediated Pd catalyzed 5-exo cyclization. Under optimized reaction condition, Pd catalyzed carbonylative protocol successfully applied for the diverse structures of 39 examples in good to excellent yield and regioselectivity.

2-Chlorophenyl-substituted benzofuro[3,2-b]pyridines with enhanced topoisomerase inhibitory activity: The role of the chlorine substituent

A new series of 2-chloropheny-substituted benzofuro[3,2-b]pyridines were designed, synthesized, and evaluated for topoisomerase I and II inhibition and antiproliferative activity. Compounds 17–19, 23, 24, 26, and 27 exhibited excellent topo II inhibitory

Design, synthesis and MAO inhibitory activity of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives

A series of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives (aurones, 1–20) were synthesized and screened for their inhibitory activity against hMAO. Seventeen compounds (1–5, 7–17, 19) were found to be selective towards hMAO-B, while two w

2,4-Diaryl benzofuro[3,2-b]pyridine derivatives: Design, synthesis, and evaluation of topoisomerase inhibitory activity and cytotoxicity

Designed and synthesized twenty-four 2,4-diaryl benzofuro[3,2-b]pyridine derivatives were evaluated for topoisomerase I and II inhibitory activities as well as cytotoxicities against several human cancer cell lines. Various aryl groups such as phenyl, 2-