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GB1258334A - - Google Patents

Info

Publication number
GB1258334A
GB1258334A GB1258334DA GB1258334A GB 1258334 A GB1258334 A GB 1258334A GB 1258334D A GB1258334D A GB 1258334DA GB 1258334 A GB1258334 A GB 1258334A
Authority
GB
United Kingdom
Prior art keywords
tetrahydroquinoline
phenyl
carbon atoms
methyl
radical
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
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 filed Critical
Publication of GB1258334A publication Critical patent/GB1258334A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
    • C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/10—Aza-phenanthrenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Quinoline Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,258,334. 1,2,3,4 - Tetrahydroquinolines. CHEMISCHE WERKE HULS A.G. 9 April, 19.69 [10 April, 1968; 2Dec., 1968],No. 18078/69. Heading C2C. 1,2,3,4-tetrahydroquinolines of the general formula in which R<SP>1</SP>, R<SP>2</SP>, R<SP>3</SP> and R<SP>4</SP> denote hydrogen, alkyl radicals having 1-4 carbon atoms, alkoxy radicals having 1-4 carbon atoms, an amino group which may bear one or two alkyl radicals having 1 to 4 carbon atoms as substituent, or halogen, and R<SP>9</SP> denotes a hydrogen atom or an alkyl radical having 1-4 carbon atoms, or R<SP>1</SP> and R<SP>2</SP> or R<SP>2</SP> and R<SP>3</SP> or R<SP>3</SP> and R<SP>4</SP> may be joined to form a non-aromatic carboxylic or aromatic 6-membered ring or R<SP>1</SP> and R<SP>9</SP> may be joined to form a non-aromatic heterocyclic 6- membered ring, R<SP>5</SP> denotes hydrogen or a saturated linear or branched alkyl radical having 1-8 carbon atoms or an aryl radical which may be substituted by alkyl or alkoxy groups having 1-4 carbon atoms, R<SP>6</SP> and R<SP>8</SP> denote hydrogen or an alkyl radical having 1-10 carbon atoms and R<SP>7</SP> denotes a phenyl radical, a vinyl radical or an alkyl radical having 1 or 2 carbon atoms, with the proviso that R<SP>7</SP> cannot be an alkyl radical if R<SP>6</SP> is hydrogen, are prepared by reacting an amine, an aldehyde and an olefine of the formulµ in the presence of a strong acid at a temperature of from 0-70‹ C. and the tetrahydroquinolinium salt is converted into the free base. Using this process the following compounds have been prepared in the examples: 2,4-dimethyl-4- phenyl - 1,2,3,4 - tetrahydroquinoline; 2,4,6- trimethyl - 4 - phenyl - 1,2,3,4 - tetrahydroquinoline; 2,4,8 - trimethyl - 4 - phenyl - 1,2,3,4- tetrahydroquinoline ; 2,4 - dimethyl - 4 - phenyl - 1 - azo - 1,2,3,4 - tetrahydrophenanthrene; 2,4- dimethyl - 4 - phenyl - 6 - methoxy - 1,2,3,4- tetrahydroquinoline; 2,4,5,8 - tetramethyl - 4- phenyl - 1,2,3,4 - tetrahydroquinoline; 2- isopropyl - 4 - methyl - 4 - phenyl - 1,2,3,4- tetrahydroquinoline ; 2 - n - propyl - 4 - methyl- 4 - phenyl - 1,2,3,4 - tetrahydroquinoline; 2 - npentyl - 4 - methyl - 4 - phenyl - 1,2,3,4 - tetrahydroquinoline; 2,4 - diphenyl - 4 - methyl- 1,2,3,4 - tetrahydroquinoline; 2,4 - dimethyl - 4- vinyl - 1,2,3,4 - tetrahydroquinoline ; 2 - methyl- 4 - phenyl - 1,2,3,4-tetrahydroquinoline; 2,4- diphenyl - 1,2,3,4 - tetrahydroquinoline; 2- isopropyl - 4 - phenyl - 1,2,3,4 - tetrahydroquinoline; 1 - methyl - 4 - phenyl - 1,2,3,4-tetrahydroquinoline; 1,7 - diphenyl - 2,3,6,7 - tetrahydro- 1H,5H - benzo - [i.j] - quinolizine ; 1,7-diphenyl- 4 - methyl - 2,3,6,7 - tetrahydro - 1H,5H- benzo[i.j]-quinolizine.
GB1258334D 1968-04-10 1969-04-09 Expired GB1258334A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19681770170 DE1770170A1 (en) 1968-04-10 1968-04-10 1,2,3,4-tetrahydroquinolines
DE19681812135 DE1812135A1 (en) 1968-04-10 1968-12-02 1,2,3,4-tetrahydroquinolines

Publications (1)

Publication Number Publication Date
GB1258334A true GB1258334A (en) 1971-12-30

Family

ID=25755555

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1258334D Expired GB1258334A (en) 1968-04-10 1969-04-09

Country Status (2)

Country Link
DE (2) DE1770170A1 (en)
GB (1) GB1258334A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4801593A (en) * 1979-09-13 1989-01-31 Burroughs Wellcome Co. Chemotherapeutic agents

Also Published As

Publication number Publication date
DE1770170A1 (en) 1970-12-23
DE1812135A1 (en) 1970-09-17

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees