FR2136345A5 - 7-syn-formylbicycloheptenes - as prostaglandin inters from 7-acetoxymethylene cpds by acid hydrolysis and isomerisation - Google Patents

7-syn-formylbicycloheptenes - as prostaglandin inters from 7-acetoxymethylene cpds by acid hydrolysis and isomerisation

Info

Publication number
FR2136345A5
FR2136345A5 FR7212798A FR7212798A FR2136345A5 FR 2136345 A5 FR2136345 A5 FR 2136345A5 FR 7212798 A FR7212798 A FR 7212798A FR 7212798 A FR7212798 A FR 7212798A FR 2136345 A5 FR2136345 A5 FR 2136345A5
Authority
FR
France
Prior art keywords
syn
isomerisation
acetoxymethylene
inters
cpds
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
FR7212798A
Other languages
French (fr)
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 claimed from GB922371*[A external-priority patent/GB1353922A/en
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Application granted granted Critical
Publication of FR2136345A5 publication Critical patent/FR2136345A5/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
    • C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/516—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of nitrogen-containing compounds to >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
    • C07D321/02—Seven-membered rings
    • C07D321/10—Seven-membered rings condensed with carbocyclic rings or ring systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Cpds. of formula (I) and precursors (II): (where R1 is halogen an R2 is cyano, carbamoyl, 2-6C alkoxycarbonyl or (1-6C-n-alkyl)carbamoyl, or (in II) chloroformyl, and R3 is alkyl, alkanoyl, alkanesulphonyl or arenesulphonyl (is not >7C) are key-inters. for the synthesis of prostaglandins, free from the danger of isomerisation. (I) are prepd. by hydrolysis of (II) with 2-N HCl + dioxane at 85 degrees C; the choice of acid is critical for the trouble-free isomerisation of the intermediate anti-form to the syn-form (X). In an example, 5-chloro-7-syn-formylbicyclo 2,2,1[hept-2-ene-5-carbonitrile is obtd. by hydrolysing 25.8 g. 7-acetoxymethylene-5-chlorobicyclo- 2,2,1[ hept-2-ene-5-carbonitrile in 360g dioxane with 80 ml 2-N HCl.
FR7212798A 1971-04-13 1972-04-12 7-syn-formylbicycloheptenes - as prostaglandin inters from 7-acetoxymethylene cpds by acid hydrolysis and isomerisation Expired FR2136345A5 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB922371*[A GB1353922A (en) 1971-04-13 1971-04-13 Bicycloheptene derivatives
GB5840071 1971-12-16

Publications (1)

Publication Number Publication Date
FR2136345A5 true FR2136345A5 (en) 1972-12-22

Family

ID=26242802

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7212798A Expired FR2136345A5 (en) 1971-04-13 1972-04-12 7-syn-formylbicycloheptenes - as prostaglandin inters from 7-acetoxymethylene cpds by acid hydrolysis and isomerisation

Country Status (15)

Country Link
JP (1) JPS5629651B1 (en)
AT (1) AT322531B (en)
BE (1) BE782064A (en)
CA (1) CA1003431A (en)
CH (1) CH577462A5 (en)
DE (1) DE2217930C2 (en)
ES (1) ES401729A1 (en)
FI (1) FI56373C (en)
FR (1) FR2136345A5 (en)
HU (1) HU166421B (en)
IE (1) IE36248B1 (en)
NL (1) NL182640C (en)
NO (1) NO137121C (en)
SE (1) SE392891B (en)
YU (1) YU98172A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2348183A1 (en) * 1976-04-14 1977-11-10 Ici Ltd NEW ((1S, 4R, 5R) -5-DIALKOXYMETHYL-4-HYDROXYCYCLOPENT-2-ENYL) -ACETIC ACID DERIVATIVES AND THEIR PREPARATION

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1430105A (en) * 1973-05-15 1976-03-31 Ici Ltd Bicyclo-octane derivatides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2348183A1 (en) * 1976-04-14 1977-11-10 Ici Ltd NEW ((1S, 4R, 5R) -5-DIALKOXYMETHYL-4-HYDROXYCYCLOPENT-2-ENYL) -ACETIC ACID DERIVATIVES AND THEIR PREPARATION

Also Published As

Publication number Publication date
HU166421B (en) 1975-03-28
NO137121C (en) 1978-01-04
IE36248B1 (en) 1976-09-15
FI56373B (en) 1979-09-28
YU98172A (en) 1983-04-27
JPS5629651B1 (en) 1981-07-09
DE2217930C2 (en) 1983-03-17
AT322531B (en) 1975-05-26
IE36248L (en) 1972-10-13
FI56373C (en) 1980-01-10
BE782064A (en) 1972-10-13
CA1003431A (en) 1977-01-11
NO137121B (en) 1977-09-26
NL7204874A (en) 1972-10-17
DE2217930A1 (en) 1972-10-19
CH577462A5 (en) 1976-07-15
NL182640C (en) 1988-04-18
SE392891B (en) 1977-04-25
NL182640B (en) 1987-11-16
ES401729A1 (en) 1975-11-01

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