GB1086978A - Improvements in or relating to the preparation of 7-oxobenzonorbornene derivatives - Google Patents

Improvements in or relating to the preparation of 7-oxobenzonorbornene derivatives

Info

Publication number
GB1086978A
GB1086978A GB41944/66A GB4194466A GB1086978A GB 1086978 A GB1086978 A GB 1086978A GB 41944/66 A GB41944/66 A GB 41944/66A GB 4194466 A GB4194466 A GB 4194466A GB 1086978 A GB1086978 A GB 1086978A
Authority
GB
United Kingdom
Prior art keywords
carbon atoms
compound
general formula
compounds
alkyl group
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
GB41944/66A
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.)
Shionogi and Co Ltd
Original Assignee
Shionogi and Co 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
Application filed by Shionogi and Co Ltd filed Critical Shionogi and Co Ltd
Publication of GB1086978A publication Critical patent/GB1086978A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C49/755—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups a keto group being part of a condensed ring system with two or three rings, at least one ring being a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
    • C07C13/605—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings with a bridged ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/266—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of hydrocarbons and halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
    • C07C17/354—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by hydrogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/24—Halogenated aromatic hydrocarbons with unsaturated side chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/20—Preparation of ethers by reactions not forming ether-oxygen bonds by hydrogenation of carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • 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
    • C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
    • C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
    • C07C49/675—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having three rings
    • 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
    • C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
    • C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
    • C07C2603/66—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing five-membered rings

Landscapes

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

Abstract

The invention relates to a 7-methylenebenzonorborna-2,5-diene compound of the general formula <FORM:1086978/C4-C5/1> in which R is hydrogen or alkyl group having not more than 5 carbon atoms, R1 and R11 are each an alkyl group having not more than five carbon atoms, an aryl group or aralkyl group having not more than fifteen carbon atoms and to the corresponding 7-methylenebenzonorbornene compounds of the general formula <FORM:1086978/C4-C5/2> Compounds claimed per se are 7-isopropylidenebenzonorborna - 2,5 - diene and 7 - isopropylidenebenzonorbornene. The compounds may be prepared by reacting a 1,2-dihalogenobenzene compound of the general formula in which R is H or alkyl group having not more than five carbon atoms and X and Y are each a halogen atom with a fulvene compound of the general formula <FORM:1086978/C4-C5/3> in which R1 and R11 are each an alkyl group having not more than five carbon atoms, an aryl group or an aralkyl group having not more than fifteen carbon atoms in the presence of dehalogenating agent to give the diene compound of Formula 3 which is hydrogenated to give a benzonorbornene compound of Formula 4.ALSO:The invention relates to the process for preparing 7-oxobenzonorbornene derivatives comprising reacting a 1,2-dihalogenobenzene compound of the general formula <FORM:1086978/C2/1> in which R is a hydrogen atom, an alkyl group having not more than five carbon atoms, an alkoxy group having not more than five carbon atoms or a halogen atom and X and Y are each a halogen atom, with a fulvene compound of the general formula <FORM:1086978/C2/2> in which R1 and R11 are each an alkyl group having not more than five carbon atoms, an aryl group or an aralkyl group having not more than fifteen carbon atoms in the presence of a dehalogenating agent to give a 7-methylenebenzonoborna-2,5-diene compound of the general formula <FORM:1086978/C2/3> hydrogenating the latter with one mol equivalent of hydrogen to saturate the double bond at the 2-position and oxidizing the resultant 7-methylenebenzonorborn compound of the general formula <FORM:1086978/C2/4> to give a 7-oxobenzonorbornene compound of the general formula <FORM:1086978/C2/5> The invention also relates to compounds of the general formulae (III) and (VI) above. Compounds claimed per se are 41-fluoro-7-isopropylidenebenzonorbornene 41 - methoxy-7-isopropylidenebenzonorbornene, 41 - chloro - 7 - isopropylidenebenzonorbornene, 41 - methyl-7-isopropylidenebenzonorbornene and the corresponding 2,5-diene compounds.
GB41944/66A 1965-09-21 1966-09-20 Improvements in or relating to the preparation of 7-oxobenzonorbornene derivatives Expired GB1086978A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP5796665 1965-09-21
JP5796765 1965-09-21

Publications (1)

Publication Number Publication Date
GB1086978A true GB1086978A (en) 1967-10-11

Family

ID=26399053

Family Applications (1)

Application Number Title Priority Date Filing Date
GB41944/66A Expired GB1086978A (en) 1965-09-21 1966-09-20 Improvements in or relating to the preparation of 7-oxobenzonorbornene derivatives

Country Status (3)

Country Link
CH (1) CH477389A (en)
DE (1) DE1593435A1 (en)
GB (1) GB1086978A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104151132B (en) * 2005-12-12 2016-07-06 先正达参股股份有限公司 The preparation method of amine

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104151132B (en) * 2005-12-12 2016-07-06 先正达参股股份有限公司 The preparation method of amine

Also Published As

Publication number Publication date
CH477389A (en) 1969-08-31
DE1593435A1 (en) 1970-10-15

Similar Documents

Publication Publication Date Title
ES399057A1 (en) Dereivatives of 17alpha-hydroxyandrost-4-ene-17beta-carboxylic acids
RO82370B (en) Process for preparing 9-amino-dibenzopyran derivatives
GB1086978A (en) Improvements in or relating to the preparation of 7-oxobenzonorbornene derivatives
SE7501375L (en)
ES333336A1 (en) A method of preparing a derived compound of isoquinolein (Machine-translation by Google Translate, not legally binding)
ES422921A1 (en) Process for the preparation of steroidal spirolactones and intermediates
GB984022A (en) D-homoandrost-9(11)-ene-18-nitrile derivatives and their preparation
ES444369A1 (en) Dienic derivatives of the androstane series and process
RO78871B (en) Process for preparing pyridylurea and pyridylthiourea derivatives
GB1369386A (en) Glycidyl-urethane compounds processes for their manufacture and their use
ES430587A1 (en) Procedure for the preparation of 4 amino-3,5-dihalogeno-feniletanolaminas. (Machine-translation by Google Translate, not legally binding)
ES433143A1 (en) N,n-diethyl-4-(2,4-dinitro-6-alkylsulfonylphenylazo)-2-alkoxy-5-alkyl-carbonylaminoanilines
ES423817A1 (en) D-2-substituted-6-alkyl-8-substituted ergolines and process for preparing same
GB845486A (en) Improvements in or relating to 2-diarylalkyl-3,4,5,6-tetrahydropyrimidines
GB1110725A (en) Process for preparing cyloheptimidazolinium halides
ES387238A1 (en) Bicyclotridecyl ethers
ES389533A1 (en) 5-substituted-5h-dibenzo a,d cycloheptene derivatives
GB1352089A (en) Bis-styryltriazoles their use for the optical brightening of organic materials and processes for their manufacture
ES428132A1 (en) Alkylated pregnanes
ES389282A1 (en) Derivatives of 1,2-diphenyl-ethane
ES437041A1 (en) A procedure for preparing 1-ftalazone derivatives. (Machine-translation by Google Translate, not legally binding)
ES446566A1 (en) A procedure for the preparation of derivatives of 1-amino- (replaced) -3-4&#39;-0-5&#39;-tiazol (replaced) -2-oxi-2-propanol. (Machine-translation by Google Translate, not legally binding)
ES431234A1 (en) 15{40 ,16{40 -Lower alkoxymethylidene-digitoxins
ES8403442A1 (en) (Arylmethyl)aryl-amino-cyclohexanols, -cyclohexanes, -cyclohexenes and intermediates thereof, a process for preparing the same and their use as medicaments.
ES312151A1 (en) A method of preparing new indoliletilguanidins. (Machine-translation by Google Translate, not legally binding)