GB374627A - Process for the production of synthetic bodies similar to papaverine - Google Patents

Process for the production of synthetic bodies similar to papaverine

Info

Publication number
GB374627A
GB374627A GB1670431A GB1670431A GB374627A GB 374627 A GB374627 A GB 374627A GB 1670431 A GB1670431 A GB 1670431A GB 1670431 A GB1670431 A GB 1670431A GB 374627 A GB374627 A GB 374627A
Authority
GB
United Kingdom
Prior art keywords
methyl
phenyl
methylenedioxyphenyl
dihydroisoquinoline
methylenedioxyisoquinoline
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
GB1670431A
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to GB1670431A priority Critical patent/GB374627A/en
Publication of GB374627A publication Critical patent/GB374627A/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
    • C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
    • C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

3-Methylisoquinoline derivatives which contain a phenyl or alkoxyphenyl or pyridyl group in the 1-position are prepared by dehydrogenation of the corresponding 3 : 4-dihydro compounds. Examples are given of the dehydrogenation with palladium of 1-phenyl-3-methyl-6 : 7-methylenedioxy - 3 : 4 - dihydroisoquinoline to 1-phenyl-3-methyl-6 : 7-methylenedioxyisoquinoline, and of 1-(3<1> : 4<1>-methylenedioxyphenyl)-3 - methyl - 6 : 7 - methylenedioxy-3 : 4 - dihydroisoquinoline, 1 - (b - pyridyl) - 3-methyl-6 : 7-methylenedioxy - 3 : 4 - dihydroisoquinoline and 1-phenyl-3-methyl-6 : 7-dimethoxy-3 : 4-dihydroisoquinoline to the corresponding dehydro isoquinoline compounds.ALSO:3-Methylisoquinoline derivatives which contain a phenyl or alkoxyphenyl or pyridyl group in the 1-position are prepared by condensation and ring closure of 1-(4<1> : 5<1>-dialkoxy- or methylenedioxy-phenyl)-2-aminopropanes with benzoic acid, nicotinic acid or ethers of oxybenzoic acids, e.g. veratric and piperonylic acids, followed by dehydrogenation of the products. The resulting compounds possess therapeutic properties similar to those of papaverine. According to the examples, (1) 1-phenyl-3-methyl-6 : 7-methylenedioxyisoquinoline is obtained by heating the amide obtained from 1-(4<1> : 5<1>-methylenedioxyphenyl)-2-aminopropane and benzoyl chloride, with phosphorus oxychloride to effect ring closure and the 3 : 4-dihydro product then dehydrogenated with palladium black; (2) 1-(3<1> : 4<1>-methylenedioxyphenyl)-3-methyl-6 : 7-methylenedioxyisoquinoline is obtained in the same way from 1-(4<1> : 5<1>-methylenedioxyphenyl)-2-aminopropane and piperonylic acid chloride; (3) nicotinic acid chloride is heated with 1-(4<1> : 5<1>-methylenedioxyphenyl)-2-aminopropane, the resulting amide converted into the dihydroisoquinoline compound by means of phosphorus oxychloride, and the product dehydrogenated with palladium to 1-b -pyridyl-3-methyl-6 : 7-methylenedioxyisoquinoline; (4) the amine (CH3O)2 = C6H3 -- CH2 -- CH (CH3) NH2 is benzoylated, ring closure of the resulting amide effected with phosphorus oxychloride and the product dehydrogenated with palladium black to yield 1-phenyl-3-methyl-6 : 7-dimethoxyisoquinoline.
GB1670431A 1931-06-08 1931-06-08 Process for the production of synthetic bodies similar to papaverine Expired GB374627A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1670431A GB374627A (en) 1931-06-08 1931-06-08 Process for the production of synthetic bodies similar to papaverine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1670431A GB374627A (en) 1931-06-08 1931-06-08 Process for the production of synthetic bodies similar to papaverine

Publications (1)

Publication Number Publication Date
GB374627A true GB374627A (en) 1932-06-16

Family

ID=10082150

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1670431A Expired GB374627A (en) 1931-06-08 1931-06-08 Process for the production of synthetic bodies similar to papaverine

Country Status (1)

Country Link
GB (1) GB374627A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2154500A1 (en) * 1971-09-22 1973-05-11 Rolland Sa A
EP0491441A1 (en) * 1990-12-17 1992-06-24 Shell Internationale Researchmaatschappij B.V. Fungicidal isoquinoline derivatives

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2154500A1 (en) * 1971-09-22 1973-05-11 Rolland Sa A
EP0491441A1 (en) * 1990-12-17 1992-06-24 Shell Internationale Researchmaatschappij B.V. Fungicidal isoquinoline derivatives
WO1992011242A1 (en) * 1990-12-17 1992-07-09 Shell Internationale Research Maatschappij B.V. Fungicidal isoquinoline derivatives

Similar Documents

Publication Publication Date Title
US3301857A (en) Spiro
US3557119A (en) 2,3,7,8,9,9a-hexahydro-1h-benzo(d,e)(1,7) naphthyridine derivatives
WHALEY et al. Synthesis of Isoquinoline Derivatives
GB374627A (en) Process for the production of synthetic bodies similar to papaverine
MURRAY et al. CYCLIZATION OF 3-AMINOPYRIDINE 1-OXIDE WITH ETHOXYMETHYLENEMALONIC ESTER TO FORM 4-HYDROXY-1, 7-NAPHTHYRIDINE AND ITS 4-CHLORO DERIVATIVE
US2723270A (en) Thiosemicarbazones of pyridylaldehydes and pyridylketones
DE69521174T2 (en) ANTHRACINE DERIVATIVES WITH ANTITUARY EFFECT AND THEIR USE
IE37655L (en) Derivatives of 1-phenoxy-3-aminopropane-2-ol.
US4107167A (en) Alkyl α-[3-(pyridyl)-anilinomethylene]acetoacetates
Govindachari et al. 575. Syntheses of protoberberine alkaloids
US1941647A (en) Process for the manufacture of ether derivatives of 1-benzyl-3-methyl-isoquinoline
US2728769A (en) Alkoxybenzylisoquinolines and salts thereof
US3544577A (en) 1 - pyridyl - 1,2,3,4 - tetrahydroisoquinoline substitution products and salts thereof
Raymond Tetrahydrofolate Coenzyme models: Synthesis of tetrahydroimidazoisoquinolines and tetrahydroimidazoquinolines
US2877226A (en) Novel quinolizine compounds and proc-
US3117970A (en) 3, 4-benzoaporphine and derivatives thereof
Govindachari et al. Synthesis of quinolizine derivatives
US3153043A (en) 1-naphthylmethyl-2-lower alkyl-1, 2, 3, 4-tetrahydroisoquinolines
Sugasawa et al. Extension of Bischler-Napieralski reaction—I: Synthesis of isoquinoline derivatives: A synthesis of rac.-apomorphine dimethyl ether
Harwood et al. Isoquinoline derivatives
US3553218A (en) 2-oxo-7-phenyl-1,2,3,4,6,7-hexahydro-11bh- benzo(a)quinolizines
Bell et al. The Polonovski rearrangement of benzylideneaminoacetic acid N-oxides with acid anhydrides
GB685748A (en) Improvements in or relating to isoquinoline derivatives
US3928611A (en) Tris- and tetrakis- (1,2,3,4-tetrahydroisoquinoline) and -{8 3,4-dihydroisoquinoline{9 {0 compounds in inhibiting and dissolving blood clots
US2719150A (en) Process for the manufacture of octahydroisoquinoline derivatives and intermediates therein