GB987433A - Process for the manufacture of tetracyclic compounds - Google Patents

Process for the manufacture of tetracyclic compounds

Info

Publication number
GB987433A
GB987433A GB2400361A GB2400361A GB987433A GB 987433 A GB987433 A GB 987433A GB 2400361 A GB2400361 A GB 2400361A GB 2400361 A GB2400361 A GB 2400361A GB 987433 A GB987433 A GB 987433A
Authority
GB
United Kingdom
Prior art keywords
group
formula
compound
acid
ester
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
GB2400361A
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.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst 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 Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB987433A publication Critical patent/GB987433A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

The invention comprises compounds of the formula <FORM:0987433/C2/1> in which R represents a hydrogen atom or a methyl group, R1 represents a hydrogen atom, an alkyl group containing 1 to 4 carbon atoms or a carboxylic acyl group and R2 represents a hydrogen atom or halogen atom. The novel tetracyclic compounds are made by reacting a compound of the formula <FORM:0987433/C2/2> in which the grouping -O-alkylene-O-represents the divalent radical of an aliphatic 1:2-diol or 1:3-diol at an elevated temperature with triphenyl phosphonium acetylide, reacting the resulting compound of the formula <FORM:0987433/C2/3> at an elevated temperature with a compound or compounds yielding an anion of the formula <FORM:0987433/C2/4> in which R1 represents an alkyl group containing 1 to 4 carbon atoms (for example, with an alkali metal salt of a malonic ester or with a malonic ester and an alkali metal alcoholate), treating the resulting condensation product with an acid to split the ketal grouping, removing any halogen atom present, if desired, by catalytic hydrogenation, and causing a strongly basic condensation agent to act on the compound so obtained with the exclusion of oxygen. The aldehyde starting materials (ii) are made by condensing an acetophenone or a benzaldehyde with a succinic acid ester, catalytically hydrogenating the alkylidene so obtained, subjecting the latter to ring closure with polyphosphoric acid, ketalizing the resulting tetralone carboxylic acid ester, reducing the carboxylic ester group to the hydroxymethyl group, esterifying the latter group with sulphonic acid chloride, converting the product by solvolysis with an alkali metal cyanide into the nitrile, reducing the nitrile group to the aldehyde and, if desired, splitting the ketal grouping with a dilute acid. A detailed example is given.
GB2400361A 1960-07-01 1961-07-03 Process for the manufacture of tetracyclic compounds Expired GB987433A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF31554A DE1129480B (en) 1960-07-01 1960-07-01 Process for the preparation of tetracyclic compounds

Publications (1)

Publication Number Publication Date
GB987433A true GB987433A (en) 1965-03-31

Family

ID=7094245

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2400361A Expired GB987433A (en) 1960-07-01 1961-07-03 Process for the manufacture of tetracyclic compounds

Country Status (3)

Country Link
CH (1) CH408909A (en)
DE (1) DE1129480B (en)
GB (1) GB987433A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4316985A (en) * 1979-01-16 1982-02-23 Hoffmann-La Roche Inc. Cyclic compounds

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1068706B (en) * 1959-11-12 Badische Anilin- S. Soda-Faforik Aktiengesellschaft, Ludwigshafen/Rhein Process for the preparation of compounds of the / monylidene grater
DE1070173B (en) * 1959-12-03 Badische Anilin- S. Soda-Fabrik Aktiengesellschaft, Ludwigshafen / Rhein Process for the preparation of 13- [2 ', 6', 6'-trimethylcyclohexen- (l ') - yl- (l')] - 3,7, ll-trimethyltridecahexaene - (2,4,6,8,10, 12) - säureil) or their esters
DE1068705B (en) * 1959-11-12 Badische Anilin- & Soda-Fabrik Aktiengesellschaft, Ludwigshafen/Rhein Process for the preparation of compounds of the / S-Ionyl'id'enäthyliden series
DE1068709B (en) * 1959-11-12 Badische Anilin- S. Soda-Faibrik Aktiengesellschaft, Ludwigshafen/Rhein Process for the synthesis of compounds of the axerophthalene series
DE1068702B (en) * 1959-11-12 Badische Anilin- &. Soda-Fabrik Aktiengesellschaft, Ludwigshafen/Rhein Process for the production of vitamin A and its biologically active derivatives
DE1059900B (en) * 1957-09-03 1959-06-25 Basf Ag Process for the preparation of compounds of the vitamin A series
DE1068710B (en) * 1958-08-06 1959-11-12 Badische Anilin- &. Soda-Fabrik Aktiengesellschaft, Ludwigshafen/Rhein Process for the preparation of compounds of the beta-ionylidene ethylidene series

Also Published As

Publication number Publication date
DE1129480B (en) 1962-05-17
CH408909A (en) 1966-03-15

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