GB734142A - Process of producing 3-substituted-4-hydroxycoumarins - Google Patents

Process of producing 3-substituted-4-hydroxycoumarins

Info

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
Application number
GB6349/53A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
WERNER SPIESS
Aurubis AG
Original Assignee
WERNER SPIESS
Norddeutsche Affinerie AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by WERNER SPIESS, Norddeutsche Affinerie AG filed Critical WERNER SPIESS
Publication of GB734142A publication Critical patent/GB734142A/en
Expired legal-status Critical Current

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.
GB6349/53A 1952-03-08 1953-03-06 Process of producing 3-substituted-4-hydroxycoumarins Expired GB734142A (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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
NL162854B (en) * 1950-01-31 Asea Ab METHOD OF MANUFACTURE OF BARS OR WIRE OF A COMPOSITE MATERIAL BY HYDROSTATIC EXTRUDING.

Cited By (4)

* Cited by examiner, † Cited by third party
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
NL80964C (en)
FR1070465A (en) 1954-07-27
DE947164C (en) 1956-08-09
CH316026A (en) 1956-09-15
GB734143A (en) 1955-07-27

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