GB1373399A - Preparation of thalicarpine and related compounds - Google Patents

Preparation of thalicarpine and related compounds

Info

Publication number
GB1373399A
GB1373399A GB5676771A GB5676771A GB1373399A GB 1373399 A GB1373399 A GB 1373399A GB 5676771 A GB5676771 A GB 5676771A GB 5676771 A GB5676771 A GB 5676771A GB 1373399 A GB1373399 A GB 1373399A
Authority
GB
United Kingdom
Prior art keywords
compound
thalicarpine
preparation
compounds
related compounds
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
GB5676771A
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.)
Kupchan S M
Liepa A J
Original Assignee
Kupchan S M
Liepa A J
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 Kupchan S M, Liepa A J filed Critical Kupchan S M
Priority to GB5676771A priority Critical patent/GB1373399A/en
Priority to US05/467,986 priority patent/US3976652A/en
Publication of GB1373399A publication Critical patent/GB1373399A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/18—Aralkyl radicals
    • C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • C07C205/38—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. nitrodiphenyl ethers

Abstract

1373399 Thalicarpine and related compounds S M KUPCHAN and A J LIEPA 7 Dec 1971 56767/71 Heading C2C The compounds I in which R and R 1 are alkyl, aryl, aralkyl or alkaryl are prepared by reaction of a compound II with a compound III in a dialkyl alkanoylamide in the presence of an alkali metal hydride to give a compound IV reduction of the compound IV with nascent hydrogen to give a compound V and substitution on the nitrogen of the tetrahydroquinolinium moiety of the compound V of an R 1 group. The compounds III and methods of preparation thereof are described in Specification 1,373,399.
GB5676771A 1971-12-07 1971-12-07 Preparation of thalicarpine and related compounds Expired GB1373399A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB5676771A GB1373399A (en) 1971-12-07 1971-12-07 Preparation of thalicarpine and related compounds
US05/467,986 US3976652A (en) 1971-12-07 1974-05-08 Isoquinoline compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5676771A GB1373399A (en) 1971-12-07 1971-12-07 Preparation of thalicarpine and related compounds

Publications (1)

Publication Number Publication Date
GB1373399A true GB1373399A (en) 1974-11-13

Family

ID=10477488

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5676771A Expired GB1373399A (en) 1971-12-07 1971-12-07 Preparation of thalicarpine and related compounds

Country Status (1)

Country Link
GB (1) GB1373399A (en)

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Legal Events

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