GB663418A - Manufacture of substituted coumarans and dihydrofurochromones - Google Patents
Manufacture of substituted coumarans and dihydrofurochromonesInfo
- Publication number
- GB663418A GB663418A GB1262949A GB1262949A GB663418A GB 663418 A GB663418 A GB 663418A GB 1262949 A GB1262949 A GB 1262949A GB 1262949 A GB1262949 A GB 1262949A GB 663418 A GB663418 A GB 663418A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- reaction
- dihydrofurochromones
- acetylcoumaran
- hydroxycoumaran
- 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)
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Dihydrofurochromones of the general formula IV in which R represents a lower alkyl group are made by the following series of reactions <FORM:0663418/IV (b)/1> The 6-hydroxy-5-acetylcoumaran II is prepared (1) by reacting 6-hydroxycoumaran with acetonitrile according to the Hoesch reaction, (2) by reacting 6-hydroxycoumaran with an acetylating agent, e.g. acetyl chloride, in the presence of a condensing agent such as aluminium chloride, or (3) by subjecting 6-acetoxycoumaran to the Fries reaction, i.e. by treatment with aluminium chloride in the presence of dry nitrobenzene. The 6-hydroxy-5-acetylcoumaran is then submitted to the Claisen reaction using an ester of the acid R-COOH to give the 6-hydroxy-5-b -ketoacylcoumaran III which is cyclo-dehydrated, e.g. by treatment with sulphuric or hydrochloric acid dissolved in alcohol or acetic acid, to yield the dihydrofurochromone IV. Examples are given in which R in the formul is methyl, ethyl or propyl.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1262949A GB663418A (en) | 1948-05-11 | 1948-05-11 | Manufacture of substituted coumarans and dihydrofurochromones |
| DEP42280D DE918929C (en) | 1948-05-11 | 1949-05-11 | Process for the production of furano (4 ', 5': 6, 7) chromones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1262949A GB663418A (en) | 1948-05-11 | 1948-05-11 | Manufacture of substituted coumarans and dihydrofurochromones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB663418A true GB663418A (en) | 1951-12-19 |
Family
ID=10008214
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1262949A Expired GB663418A (en) | 1948-05-11 | 1948-05-11 | Manufacture of substituted coumarans and dihydrofurochromones |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE918929C (en) |
| GB (1) | GB663418A (en) |
-
1948
- 1948-05-11 GB GB1262949A patent/GB663418A/en not_active Expired
-
1949
- 1949-05-11 DE DEP42280D patent/DE918929C/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE918929C (en) | 1954-10-07 |
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