GB1017704A - 2, 3-dihydrofuro[3, 2-c]quinoline derivatives and production thereof - Google Patents

2, 3-dihydrofuro[3, 2-c]quinoline derivatives and production thereof

Info

Publication number
GB1017704A
GB1017704A GB4546563A GB4546563A GB1017704A GB 1017704 A GB1017704 A GB 1017704A GB 4546563 A GB4546563 A GB 4546563A GB 4546563 A GB4546563 A GB 4546563A GB 1017704 A GB1017704 A GB 1017704A
Authority
GB
United Kingdom
Prior art keywords
dihydrofuro
quinoline
general formula
quinolyl
formula above
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
GB4546563A
Inventor
Hideo Kano
Yasuo Makisumi
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
Priority to GB4546563A priority Critical patent/GB1017704A/en
Publication of GB1017704A publication Critical patent/GB1017704A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

The invention comprises a process for preparing 2,3-dihydrofuro[3,2-c]-quinoline derivatives which comprises heating a quinolyl ether represented by the formula <FORM:1017704/C2/1> wherein R is hydrogen, or alkyl or alkenyl having not more than five carbon atoms, and R1 and R11 each is hydrogen or alkyl having not more than five carbon atoms, or a quinolyl alcohol represented by the formula <FORM:1017704/C2/2> wherein R, R1 and R11 each has the same significance as designated above, in the presence or absence of pyridine hydrochloride, to give a 2,3 - dihydrofuro[3,2-c]quinoline represented by the formula <FORM:1017704/C2/3> wherein R, R1 and R11 each has the same significance as designated above; and the following compounds of the last general formula above:- 2,2,4 - trimethyl - 2,3 - dihydrofuro[3,2-c]-quinoline, 2,3,4 - trimethyl - 2,3 - dihydrofuro[3,2-c]-quinoline, 2 - methyl - 4 - (3 - butenyl) - 2,3 - dihydrofuro[3,2-c]quinoline, and 2,2 - dimethyl - 4 - (3 - butenyl) - 2,3 - dihydrofuro[3,2-c]quinoline. The compounds of the last general formula above and their non-toxic acid addition salts are stated to be useful as analgesic and anti-inflammatory agents. Quinolyl alcohols of the second general formula above are prepared by heating a compound of the first general formula above at a lower temperature than is necessary to convert it to a compound of the last general formula above. Quinolyl ethers of the first general formula above can be prepared by the reaction of the corresponding 4-hydroxyquinoline with an allyl halide.
GB4546563A 1963-11-18 1963-11-18 2, 3-dihydrofuro[3, 2-c]quinoline derivatives and production thereof Expired GB1017704A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB4546563A GB1017704A (en) 1963-11-18 1963-11-18 2, 3-dihydrofuro[3, 2-c]quinoline derivatives and production thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4546563A GB1017704A (en) 1963-11-18 1963-11-18 2, 3-dihydrofuro[3, 2-c]quinoline derivatives and production thereof

Publications (1)

Publication Number Publication Date
GB1017704A true GB1017704A (en) 1966-01-19

Family

ID=10437310

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4546563A Expired GB1017704A (en) 1963-11-18 1963-11-18 2, 3-dihydrofuro[3, 2-c]quinoline derivatives and production thereof

Country Status (1)

Country Link
GB (1) GB1017704A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113717185A (en) * 2021-08-19 2021-11-30 云南省烟草农业科学研究院 Quinoline alkaloid compound with antibacterial activity in cigar rhizome and preparation method and application thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113717185A (en) * 2021-08-19 2021-11-30 云南省烟草农业科学研究院 Quinoline alkaloid compound with antibacterial activity in cigar rhizome and preparation method and application thereof

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