GB948080A - Benzopyranone derivatives and processes for their production - Google Patents
Benzopyranone derivatives and processes for their productionInfo
- Publication number
- GB948080A GB948080A GB199861A GB199861A GB948080A GB 948080 A GB948080 A GB 948080A GB 199861 A GB199861 A GB 199861A GB 199861 A GB199861 A GB 199861A GB 948080 A GB948080 A GB 948080A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- furano
- methylisoxazolyl
- benzopyran
- dimethoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention comprises furano chromones of the general formula: <FORM:0948080/C2/1> (in which R is the 5-methyl-isoxazolyl-(3)- or the 3-methyl-isoxazolyl-(5)- radical, R1 and R2 represent alkyl radicals having at most 4 carbon atoms, which may also be bound to each other directly or by way of an oxygen atom, and Z represents a straight or branched alkylene radical having at most 6 carbon atoms), together with a process for their preparation by condensing by means of an alkali metal, alkali metal hydride, amide, or alcoholate, khellinone and a lower alkyl ester of 5-methyl-isoxazole -3- carboxylic acid or 3-methylisoxazole -5- carboxylic acid to form a compound of general formula: <FORM:0948080/C2/2> converting this compound by treatment with an agent which splits off water into a furanochromone, partially hydrolysing the latter, advantageously by means of hydrochloric acid or hydrobromic acid, to form a compound of general formula: <FORM:0948080/C2/3> and reacting the latter in the presence of an acid binding agent, with a reactive ester of a basic alcohol of formula 1-10-ZNR1R2. The novel bases may be converted into their acid addition salts, e.g. picrates. Examples detail the preparation of 4-(b -diethylamino ethoxy) -7- [51-methylisoxazolyl-(31)] -9- methoxy -5H- furano-[3, 2-g][1]-benzopyran -5- one and the analogous 4-(g -pyrrolidyl -(11)- propoxy)-, 4-(g -dimethylamino-propoxy)-, 4-(b -piperidino-ethoxy)- and 4- (S-morpholino-butoxy) compounds, and 4-(b -diethylamino-ethoxy) -7- [31-methylisoxazolyl-(51)] -9- methoxy -5H- furano -[3, 2-g][1] benzopyran -5- one. 5 - [51 - methyl - isoxazole - (31) - carbonylacetyl] -4, 7- dimethoxy -6- hydroxycoumarone (prepared from khellinone and 5-methyl-isoxazole -3- carboxylic acid methyl ester) is refluxed with ethanol/H2SO4 to give 7-[51-methylisoxazolyl -(31) -] -4, 9 - dimethoxy -5H- furano-[3, 2-g][1] - benzopyran -5- one which upon acid hydrolysis yields the corresponding 4-hydroxy compound. 3-Methylisoxazole -5- carboxylic acid ethyl ester similarly yields successively 5-[31-methylisoxazole-(51)-carbonylacetyl] -4, 7-dimethoxy -6- hydroxy coumarone, 7-[31-methylisoxazolyl -(51)]- 4, 9-dimethoxy -5H- furano-[3, 2g][1] benzopyran -5- one and its 4-hydroxy derivative.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH53360 | 1960-01-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB948080A true GB948080A (en) | 1964-01-29 |
Family
ID=4189182
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB199861A Expired GB948080A (en) | 1960-01-19 | 1961-01-18 | Benzopyranone derivatives and processes for their production |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB948080A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114751912A (en) * | 2022-01-20 | 2022-07-15 | 昆明医科大学 | New application of isopentenyl substituted bisphenylpyridone compound |
-
1961
- 1961-01-18 GB GB199861A patent/GB948080A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114751912A (en) * | 2022-01-20 | 2022-07-15 | 昆明医科大学 | New application of isopentenyl substituted bisphenylpyridone compound |
| CN114751912B (en) * | 2022-01-20 | 2023-03-07 | 昆明医科大学 | Application of isopentenyl substituted bisphenylpyridone compound |
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