6431-83-0

Usage

Uses

Unfortunately, the provided materials do not mention any specific applications or uses for 2,3,4,10-Tetrahydro-2,2-dimethyl-5H-pyrano[2,3-b]quinolin-5-one. Further research would be needed to determine its potential applications in various industries.

References

Fakhritidinova, Sidyakin, Yunusov, Uzbek Khim. Zh., 4, 41 (1963) Bowman, Grundon, J. Chem. Soc., C, 1084 (1966) Rashkes, Faizutidinova, Yunusov, Khim. Prir. Soedin., 6, 107 (1970)

Upstream product

• 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 
• 82912-92-3 1-(1-Hydroxy-1-methyl-ethyl)-8b-methoxy-2,2a,4,8b-tetrahydro-1H-cyclobuta[c]quinolin-3-one 
• 42522-05-4 3, 4-dihydro-2,2-dimethyl-5-methoxy-2H-pyrano-[2,3-b]quinoline 
• 7282-19-1 atanine 
• 82359-07-7 methyl 2,4-methoxyquinoline-3-acetate 
• 62-53-3 aniline 
• 996-82-7 sodium diethylmalonate 
• 14872-56-1 5-isopropyl-2-oxo-tetrahydro-furan-3-carboxylic acid ethyl ester 
• 95687-74-4 4-Methoxy-3-((E)-3-methyl-but-1-enyl)-1H-quinolin-2-one 
• 82376-58-7 (E)-2-(4-Methoxy-2-oxo-1,2-dihydro-quinolin-3-yl)-4-methyl-pent-2-enoic acid 
• 82359-22-6 4-Methoxy-3-[2-methyl-prop-(Z)-ylidene]-3H-furo[2,3-b]quinolin-2-one 
• 65112-97-2 methyl 4-methoxy-2-quinolone-3-acetate 
• 870-63-3 prenyl bromide 

Downstream Products

• 523-64-8 flindersine 
• 6391-67-9 N-Methyl-Khaplofolin 

Relevant academic research and scientific papers

Quinoline alkaloids: Synthesis of pyrano[2,3,-b]quinolines, khaplofoline, lunacrine, and demethoxylunacrine

Polyphosphoric acid (PPA)-catalyzed cyclization of 2-ono-3- vinylquinolinecarboxylic acid (1) yielded 3,4-dihydro-2,2-dimethyl-2H- pyrano[2,3-b]quinoline (4). The same reaction of 4-methoxy-2-oxo-3- vinylquinolinecarboxylic acid (1g) afforded 4-methoxy-2,2-dimethylpyrano[2,3- b]-quinoline (4g), which on hydrolysis with ethanolic hydrochloric acid gave khaplofoline (5). The Prevost reaction of 4-methoxy-3-prenylquinolin-2-one (6) using I2/HgO in acetic acid yielded 4-methoxy-2-isopropylfuro[2,3- b]quinoline (7). Compound 7 on reduction with H2/Pd-C followed by N- methylation and de-O-methylation afforded lunacrine (10a). A similar reaction sequence on 6b gave demethoxylunacrine (10b).

Quinoline Alkaloids. Synthesis of Khaplofoline, Ribalinine, and Flindersine

Reaction of 4-hydroxy-3-prenylquinolin-2(1H)one (5a) with iodine and silver acetate gave a iodopyranoquinoline (6a), which was then converted into the alkaloids khaplofoline (1) and ribalinine (2).Reaction of 5a with iodine and mercuric oxide afforded a mixture of 6a and its angular isomer 7a; the conversion of latter into flindersine (10) is described.Keywords: Pyranoquinoline Alkaloids, Khaplofoline, Ribalinine, Flindersine

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.

A NEW SYNTHESIS OF ATANINE, KHAPLOFOLINE AND THEIR ANALOGUES

Afacile synthesis of Atanine, Khaplofoline and their ananogues is described.The method involves condensation of an appropriately substituted 2-quinolone-3-acetic acid with isobutyraldehyde, as the starting point.

A NOVEL PHOTOCHEMICAL PRENYLATION REACTION OF HETEROAROMATICS INVOLVING AN ENONE FUNCTION IN THEIR RING SYSTEM

In a novel photochemical prenylation of heteroaromatics involving an enone function in their ring system, the key step is an acid-catalyzed C-C bond fission in the head-to-tail adduct formed by photocycloaddition of these heteroaromatics to 2-methyl-3-buten-2-ol to give the heteroaromatics having a 3-methylbut-2-enyl function (or its equivalent) at the α-position of the enone system.Examples using 2-quinolones, 2-pyridones, and coumarins are reported.KEYWORDS---photochemical synthesis; photochemical prenylation; 3,3-dimethylallyalation of heteroaromatics; photochemical 2+2 cycloaddition; 3-(3-methylbut-2-enyl)-2-quinolones; 2-methyl-3-buten-2-ol as prenylation reagent; synthesis of khaplofoline