6391-66-8

Usage

Uses

Used in Pharmaceutical Industry:
2,3,4,6-Tetrahydro-2,2-dimethyl-5H-pyrano[3,2-c]quinolin-5-one is used as a key intermediate in the synthesis of various bioactive molecules for medicinal applications, leveraging its unique structural features to enhance drug efficacy and target specificity.
Used in Antiviral Applications:
In the field of antiviral research, 2,3,4,6-Tetrahydro-2,2-dimethyl-5H-pyrano[3,2-c]quinolin-5-one is being studied for its potential as an antiviral agent, with the aim of developing new treatments for viral infections by targeting specific viral processes.
Used in Antifungal Applications:
2,3,4,6-Tetrahydro-2,2-dimethyl-5H-pyrano[3,2-c]quinolin-5-one is also being explored for its antifungal properties, potentially leading to the development of new antifungal drugs to combat fungal infections.
Used in Anticancer Applications:
2,3,4,6-Tetrahydro-2,2-dimethyl-5H-pyrano[3,2-c]quinolin-5-one is under investigation for its potential as an anticancer agent, with research focusing on its ability to target and inhibit the growth of cancer cells, offering a new avenue for cancer treatment.
Used in Medicinal Chemistry and Drug Discovery:
2,3,4,6-Tetrahydro-2,2-dimethyl-5H-pyrano[3,2-c]quinolin-5-one serves as a building block in medicinal chemistry, contributing to the discovery and development of novel therapeutic agents with improved pharmacological profiles.
Further research is essential to fully elucidate the properties and potential uses of 2,3,4,6-Tetrahydro-2,2-dimethyl-5H-pyrano[3,2-c]quinolin-5-one, ensuring its safe and effective application in various therapeutic areas.

Upstream product

• 91794-24-0 4-Hydroxy-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one 
• 14668-44-1 5-isopropyl-2-oxo-tetrahydro-furan-3-carboxylic acid anilide 
• 21873-59-6 3,3-bis(γ,γ-dimethylallyl)-2.4-dioxo-1,2,3,4-tetrahydroquinoline 
• 109573-27-5 4-hydroxy-3-(3-hydroxy-3-methylbutyl)quinolin-2(1H)-one 
• 109573-19-5 4-hydroxy-3-(3-methylbut-3-enyl)quinolin-2(1H)-one 
• 111094-76-9 2-methyl-2-chloromercurymethyl-3,4-dihydro-2H,5H-pyrano{3,2-c}quinolin-5-one 
• 50-00-0 formaldehyd 
• 70254-43-2 4-Hydroxy-2-quinolone 
• 541-47-9 3-Methylbutenoic acid 
• 78-79-5 isoprene 
• 870-63-3 prenyl bromide 
• 14872-56-1 5-isopropyl-2-oxo-tetrahydro-furan-3-carboxylic acid ethyl ester 
• 91794-23-9 4-keto-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyrano<3,2-c>quinolin-5-one 
• 62-53-3 aniline 

Downstream Products

• 523-64-8 flindersine 

Relevant academic research and scientific papers

A Chiral Phenanthroline Ligand with a Hydrogen-Bonding Site: Application to the Enantioselective Amination of Methylene Groups

A silver-catalyzed amination is reported that occurs at the aliphatic C3-substituent of various quinolones and pyridones. The C-H amination reaction proceeded with high site-and enantioselectivity (14 examples, 83-97% ee). The key to its success is the use of a chiral phenanthroline ligand that is attached via an ethynyl linker to the 8-position of octahydro-1H-4,7-methanoisoindol-1-one. AgPF6 (10 mol %) served as the silver source, PhI.NNs as the nitrene precursor, and 1,10-phenanthroline as the coligand. The reaction outcome can be understood by assuming a nitrene C-H insertion within a hydrogen-bonded silver complex in which a single C-H bond is exposed to the catalytic reaction center.

Acid-Catalyzed Regiodivergent Annulation of 4-Hydroxycoumarins with Isoprene: Entry to Pyranocoumarins and Pyranochromones

An acid-catalyzed regiodivergent formal [3+3] annulation of 4-hydroxycoumarins with isoprene is developed. A variety of pyranocoumarins were obtained exclusively in the presence of strong Br?nsted acid, while varying to Lewis acid delivered pyranochromones as main products. The protocol also features high atom-economy, wide substrate scope, easy scale-up, and good applications in natural product synthesis.

Simple efficient synthesis of pyranoquinoline alkaloids: Flindersine, khaplofoline, haplamine and their analogues

An efficient two step synthesis of pyranoquinoline alkaloids is described. Direct treatment of isoprene with 4-hydroxyquinolin-2(1H)-one in the presence of polyphosphoric acid furnished dihydroflindersine in good yield, and which on dehydrogenation led to a new synthesis of flindersine. Khaplofoline, a linear pyranoquinoline alkaloid, was obtained as a minor product. The syntheses of derivatives are also documented.

Synthesis of pyranoquinoline alkaloids via (4+2) cycloaddition reaction

An easy route to synthesize pyranoquinoline based alkaloids like flindersine, haplamine, N-methylflindersine and its derivatives were performed from the respective 4-hydroxyquinolin-2(1H)-one, dimethyl acrylic acid and para formaldehyde through generation of O-quinone methide intermediates and subjecting (4+2) cycloaddition. Further, dihydro intermediates were oxidized by DDQ.

A NEW APPROACH TO HEMITERPENOID TRICYCLIC QUINOLONES. SYNTHESIS OF N-METHYLFLINDERSINE, KHAPLOPHOLINE AND OTHER STRUCTURALLY SIMILAR ALKALOIDS

A new and general synthesis of tricyclic quinolone alkaloids is described which, by cyclization of 3-butenyl-4-hydroxyquinolones promoted by mercury(II) ion or by formic acid, affords pyranoquinolones and pyranoquinolones, respectively, with regio- and site-selectivity better than those obtained employing known methodologies. 3-Butenyl-4-hydroxyquinolones have been reacted with mercury(II) acetate to give, after work-up, the corresponding 2-(chloromercurymethyl)pyranoquinolones, which have been reductively demercurated with sodium borohydride and then dehydrogenated by treatment with DDQ.Alternatively, from the same starting compounds the "linear" isomers are obtained by formic acid-promoted cyclization.N-Methylflindersine, khaplofoline and other structurally similar alkaloids have been obtained.

MERCURY(II)-PROMOTED CYCLIZATION OF SOME 2-ALKENYLPHENOLS AND SOME CYCLIC 2-ALKENYL-1,3-DIKETONES, 3-KETO ESTERS, AND 3-KETO AMIDES: SYNTHESIS OF 2,3-DIHYDROFURAN, 3,4-DIHYDRO-2H-PYRAN, AND 2,3,4,5-TETRAHYDROOXEPIN RINGS FUSED ON CARBOCYCLIC OR ON OXYGEN

Treatment of 4-hydroxy-3-(substituted 3-buten-1-yl)-2H-pyran-2-ones, 4-hydroxy-3-(substituted 3-buten-1-yl)-2(1H)-quinolinones, 2-(substituted 3-buten-1-yl)-1,3-cyclohexanediones and 2-(substituted 3-buten-1-yl)phenols with mercuric acetate in tetrahydrof