6431-83-0

Basic information

• Product Name: 2,3,4,10-Tetrahydro-2,2-dimethyl-5H-pyrano[2,3-b]quinolin-5-one
• Synonyms: 2,3,4,10-Tetrahydro-2,2-dimethyl-5H-pyrano[2,3-b]quinolin-5-one;Haplofoline;Khaplofoline
• CAS NO: 6431-83-0
• Molecular Formula: C14H15 N O2
• Molecular Weight: 229.27
• Mol File: 6431-83-0.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,3,4,10-Tetrahydro-2,2-dimethyl-5H-pyrano[2,3-b]quinolin-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,10-Tetrahydro-2,2-dimethyl-5H-pyrano[2,3-b]quinolin-5-one(6431-83-0)
• EPA Substance Registry System: 2,3,4,10-Tetrahydro-2,2-dimethyl-5H-pyrano[2,3-b]quinolin-5-one(6431-83-0)

Safety Data

• Hazardous Substances Data: 6431-83-0(Hazardous Substances Data)

Usage

Description

Russian workers have described this pyranoquinoline alkaloid which occurs in Hapiophyllum foliosum Vved. The base crystallizes from MeOH as colourless rods and forms a series of crystalline salts and derivative, e.g. hydrochloride, m.p. 78-80°C; sulphate, m.p. 196-7°C; the bromo derivative, m.p. 186-8°C; the N-acetyl compound, m.p. 155-6°C and the N-methyl derivative with m.p. 121°C.

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

• 109573-27-5 4-hydroxy-3-(3-hydroxy-3-methylbutyl)quinolin-2(1H)-one 
• 621-10-3 N,N'-diphenylmalonamide 
• 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 
• 65112-97-2 methyl 4-methoxy-2-quinolone-3-acetate 
• 82359-07-7 methyl 2,4-methoxyquinoline-3-acetate 
• 7282-19-1 atanine 
• 870-63-3 prenyl bromide 
• 143704-15-8 3-iodo-3,4-dihydro-5-oxo-2,2-dimethyl-2H-pyrano<2,3-b>quinoline 
• 6431-84-1 4-hydroxy-3-(3-methylbut-2-enyl) quinolin-2(1H)one 
• 21873-59-6 3,3-bis(γ,γ-dimethylallyl)-2.4-dioxo-1,2,3,4-tetrahydroquinoline 
• 70254-43-2 4-Hydroxy-2-quinolone 

Downstream Products

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

Relevant articles and documents

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).

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 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