GB734142A - Process of producing 3-substituted-4-hydroxycoumarins - Google Patents
Process of producing 3-substituted-4-hydroxycoumarinsInfo
- Publication number
- GB734142A GB734142A GB6349/53A GB634953A GB734142A GB 734142 A GB734142 A GB 734142A GB 6349/53 A GB6349/53 A GB 6349/53A GB 634953 A GB634953 A GB 634953A GB 734142 A GB734142 A GB 734142A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxycoumarin
- furfurylidene
- ethyl
- give
- furan
- 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
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
- C07D311/44—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3
- C07D311/46—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3 unsubstituted in the carbocyclic ring
- C07D311/48—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3 unsubstituted in the carbocyclic ring with two such benzopyran radicals linked together by a carbon chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
3 - Substituted - 4 - hydroxycoumarins of the formula <FORM:0734142/IV (b)/1> where R1 represents a lower alkyl, phenyl or substituted phenyl group and R11 represents a lower alkyl, phenyl, substituted phenyl or a -furan group are made by reacting 4-hydroxycoumarin with a compound of the general formula R11-CH=CH-CO-R1 in the presence of 0.1-50 mol. per cent of trisodium orthophosphate, either added as such or in the form of a salt with the 4-hydroxycoumarin. The reactants may be melted together at a temperature from 100 DEG 150 DEG C. or may be heated together in an inert liquid diluent, e.g. water, at a temperature of 100 DEG to 150 DEG C. In examples: (1) and (2) furfurylidene acetone is heated with 4-hydroxycoumarin in the presence of trisodium orthophosphate to give 3-[11-(a -furan) - 21 - acetyl] - ethyl - 4 - hydroxycoumarin; (3) furfurylidene acetophenone is used in place of furfurylidene acetone in (1) to give 3 - [11 - (a - furan) - 21 - benzoyl] - ethyl - 4 - hydroxycoumarin; (4) furfurylidene methyl ethyl ketone is used in place of furfurylidene acetone to give 3-[11-(a -furan)-21-propionyl]-ethyl-4-hydroxycoumarin; and (5) and (6) benzalacetone is used in place of furfurylidene acetone to give 3-(11-phenyl-21-acetyl)-ethyl-4-hydroxycoumarin. Specification 734,143 is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DES27561A DE947164C (en) | 1952-03-08 | 1952-03-08 | Process for the preparation of 4-oxycoumarins substituted in the 3-position |
Publications (1)
Publication Number | Publication Date |
---|---|
GB734142A true GB734142A (en) | 1955-07-27 |
Family
ID=7479138
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB6349/53A Expired GB734142A (en) | 1952-03-08 | 1953-03-06 | Process of producing 3-substituted-4-hydroxycoumarins |
GB6350/53A Expired GB734143A (en) | 1952-03-08 | 1953-03-06 | 3-substituted-4-hydroxycoumarin compounds |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB6350/53A Expired GB734143A (en) | 1952-03-08 | 1953-03-06 | 3-substituted-4-hydroxycoumarin compounds |
Country Status (5)
Country | Link |
---|---|
CH (1) | CH316026A (en) |
DE (1) | DE947164C (en) |
FR (1) | FR1070465A (en) |
GB (2) | GB734142A (en) |
NL (1) | NL80964C (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994018188A1 (en) * | 1993-02-05 | 1994-08-18 | The Upjohn Company | 4-hydroxy-benzopyran-2-ones and 4-hydroxy-cycloalkyl[b]pyran-2-ones useful to treat retroviral infections |
US5852195A (en) * | 1994-05-06 | 1998-12-22 | Pharmacia & Upjohn Company | Pyranone compounds useful to treat retroviral infections |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2872457A (en) * | 1956-04-19 | 1959-02-03 | Wisconsin Alumni Res Found | Process for the preparation of 4-hydroxycoumarin derivatives |
FR2355499A1 (en) * | 1976-06-25 | 1978-01-20 | Rhone Poulenc Ind | NEW ISOINDOLINE DERIVATIVE, ITS PREPARATION AND THE COMPOSITIONS CONTAINING IT |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2427578A (en) * | 1945-04-02 | 1947-09-16 | Wisconsin Alumni Res Found | 3-substituted 4-hydroxycoumarin and process of making it |
LU30424A1 (en) * | 1950-01-31 |
-
0
- NL NL80964D patent/NL80964C/xx active
-
1952
- 1952-03-08 DE DES27561A patent/DE947164C/en not_active Expired
- 1952-08-04 FR FR1070465D patent/FR1070465A/en not_active Expired
-
1953
- 1953-03-06 GB GB6349/53A patent/GB734142A/en not_active Expired
- 1953-03-06 GB GB6350/53A patent/GB734143A/en not_active Expired
- 1953-03-06 CH CH316026D patent/CH316026A/en unknown
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994018188A1 (en) * | 1993-02-05 | 1994-08-18 | The Upjohn Company | 4-hydroxy-benzopyran-2-ones and 4-hydroxy-cycloalkyl[b]pyran-2-ones useful to treat retroviral infections |
US5686486A (en) * | 1993-02-05 | 1997-11-11 | Pharmacia & Upjohn Company | 4-hydroxy-benzopyran-2-ones and 4-hydroxy-cycloalkyl b!pyran-2-ones useful to treat retroviral infections |
US5852195A (en) * | 1994-05-06 | 1998-12-22 | Pharmacia & Upjohn Company | Pyranone compounds useful to treat retroviral infections |
US6169181B1 (en) | 1994-05-06 | 2001-01-02 | Pharmacia & Upjohn Company | Compounds useful to treat retroviral infections |
Also Published As
Publication number | Publication date |
---|---|
FR1070465A (en) | 1954-07-27 |
CH316026A (en) | 1956-09-15 |
NL80964C (en) | |
GB734143A (en) | 1955-07-27 |
DE947164C (en) | 1956-08-09 |
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