GB822181A - Substituted coumarins and the preparation thereof - Google Patents

Substituted coumarins and the preparation thereof

Info

Publication number
GB822181A
GB822181A GB934756A GB934756A GB822181A GB 822181 A GB822181 A GB 822181A GB 934756 A GB934756 A GB 934756A GB 934756 A GB934756 A GB 934756A GB 822181 A GB822181 A GB 822181A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
ethyl
coumarin
general formula
alkyl
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
GB934756A
Inventor
Karel Fucik
Milos Horicky
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.)
Spofa Spojene Farmaceuticke Zavody
Original Assignee
Spofa Spojene Farmaceuticke Zavody
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
Priority to BE546501D priority Critical patent/BE546501A/xx
Priority to NL95256D priority patent/NL95256C/xx
Priority to NL89799D priority patent/NL89799C/xx
Application filed by Spofa Spojene Farmaceuticke Zavody filed Critical Spofa Spojene Farmaceuticke Zavody
Priority to GB934756A priority patent/GB822181A/en
Priority to CH344734D priority patent/CH344734A/en
Priority to CH346224D priority patent/CH346224A/en
Priority to DES48281A priority patent/DE1020030B/en
Priority to FR1164524D priority patent/FR1164524A/en
Publication of GB822181A publication Critical patent/GB822181A/en
Expired legal-status Critical Current

Links

Classifications

    • 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)
  • Pyrane Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises 1-(chromonyl-3)-1-(4-hydroxycoumarinyl-3)-ethane, propane and butane, and a process for the preparation of 1 - (chromonyl - 3) - 1 - (4 - hydroxycoumarinyl-3) -methanes of the general formula <FORM:0822181/IV (a)/1> wherein R represents an alkyl, aralkyl or furyl group, by reacting 3-(2-salicoyl-1-substituted-ethyl) - 4 - hydroxy - coumarins of the general formula <FORM:0822181/IV (a)/2> wherein R has the above significance, with sodium and a formic acid ester to form the sodium salt of the above formula which may then be treated with acid to form the corresponding compound with a free hydroxy group. The above process may be modified in that the 3 - (2 - salicoyl - 1 - alkyl - ethyl) - 4 - hydroxy-coumarin reactant is prepared by reacting 4-hydroxy-coumarin with the trimer of an aldehyde of the formula RCHO where R represents an alkyl group in a reaction medium in which the 3,31-alkylidene bis-4-hydroxy-coumarin product is substantially insoluble, e.g. a lower alkanol, (the use of a monomeric aldehyde RCHO for the same purpose is also referred to), and hydrolysing the alkylidene product under alkaline conditions, e.g. with aqueous sodium hydroxide. In the examples, compounds of the above general formula in which R represents the methyl, ethyl and propyl group and the corresponding free hydroxy compounds are prepared. Specification 777,754 is referred to.
GB934756A 1956-03-26 1956-03-26 Substituted coumarins and the preparation thereof Expired GB822181A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
BE546501D BE546501A (en) 1956-03-26
NL95256D NL95256C (en) 1956-03-26
NL89799D NL89799C (en) 1956-03-26
GB934756A GB822181A (en) 1956-03-26 1956-03-26 Substituted coumarins and the preparation thereof
CH344734D CH344734A (en) 1956-03-26 1956-04-05 Process for the preparation of new anticoagulants
CH346224D CH346224A (en) 1956-03-26 1956-04-05 Process for the preparation of alkylidene-bis-4-oxy-coumarins
DES48281A DE1020030B (en) 1956-03-26 1956-04-06 Process for the preparation of 3- [chromonyl- (3 ') -methyl] -4-oxycoumarins
FR1164524D FR1164524A (en) 1956-03-26 1956-05-03 Process for the preparation of new anticoagulant substances and products conforming to those obtained

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB934756A GB822181A (en) 1956-03-26 1956-03-26 Substituted coumarins and the preparation thereof

Publications (1)

Publication Number Publication Date
GB822181A true GB822181A (en) 1959-10-21

Family

ID=9870198

Family Applications (1)

Application Number Title Priority Date Filing Date
GB934756A Expired GB822181A (en) 1956-03-26 1956-03-26 Substituted coumarins and the preparation thereof

Country Status (5)

Country Link
BE (1) BE546501A (en)
CH (2) CH344734A (en)
FR (1) FR1164524A (en)
GB (1) GB822181A (en)
NL (2) NL95256C (en)

Also Published As

Publication number Publication date
CH346224A (en) 1960-05-15
NL95256C (en)
NL89799C (en)
FR1164524A (en) 1958-10-10
BE546501A (en)
CH344734A (en) 1960-02-29

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