GB960181A - Substituted tetrahychroisoquinolines - Google Patents
Substituted tetrahychroisoquinolinesInfo
- Publication number
- GB960181A GB960181A GB2352259A GB2352259A GB960181A GB 960181 A GB960181 A GB 960181A GB 2352259 A GB2352259 A GB 2352259A GB 2352259 A GB2352259 A GB 2352259A GB 960181 A GB960181 A GB 960181A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tetrahydro
- dimethoxy
- acetone
- isoquinol
- 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
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1-substituted 1,2,3,4-tetrahydro-isoquinolines, specifically, <FORM:0960181/C1/1> in which R2 and R3 are hydrogen atoms or hydrocarbon groups and R111 is an alkyl group, a carboxy methyl group or a group <FORM:0960181/C1/2> are prepared by reacting a 3,4-dihydroisoquinoline compound with a methine compound R1R11-CH-Y where R1 and R11, which may be the same or different, are hydrogen atoms, carboxyl groups, hydrocarbon groups, or further groups, or further groups Y, and Y is an elec attracting group, such as a carbonyl, cyan tron nitro group. Acetone, acetyl-acetone, acetone dicarboxylic acids acetoacetic acid, malonic esters and acids and benzyl cyanide are examples of the reactive methine compounds, and the dihydroisoquinoline may be substituted in the 3,4,5,6,7 and/or 8 position by for example alkyl, aralkyl, aryl, alkenyl, alkoxy, aralkoxy, aryloxy, alkyl, aralkyl or aryl thio or disubstituted amino groups or methylene dioxy groups. A solvent medium, e.g. acetone, pyridine, or methanol, with an acid catalyst may be used, and as examples describe the preparation of a -bis(1:2:3:4-tetrahydro-6:7-dimethoxyisoquinol-1-yl) acetone, its isomers and acid addition salts; of 6:7-dimethoxy-1:2:3:4-tetrahydroisoquinol-1-yl acetone hydrochloride; and 6:7-dimethoxy-1,2,3,4-tetrahydro-isoquinol-1-yl-acetroacetic acid. The products are suitable as precursors for benzoquinolizine ring compounds of formula <FORM:0960181/C1/3> e.g.emetine, or 2-dehydro-emetine and by reacting with a compound R4CH2.COZ where Z is a halogen atom, azide group, or a -CO.CH2R4 group (and R4 is a hydrocarbon group), or a vinyl ketone R6-CO-CH=CH2 (where R6 is a hydrocarbon group) followed by cyclisation, dehydration and reduction. Examples describe the preparation of emetine from the corresponding bis-derivatives by the use of (a) acid anhydride or (b) vinyl ketone following the above stages in which a -bis (1:2:3:4-tetrahydro 6:7-dimethoxy-isoquinol-1-yl) acetone and its di-butyryl derivative is prepared, followed by the preparation of 1,3-bis (1:2:3:4-tetrahydro 6:7-dimethoxy-2(3-oxo-but-1-yl)-isoquinol-1-yl) acetone hydrochloride and (1:2:3:4-tetrahydro-6:7-dimethoxy-2-(31-oxo-but-11-yl) isoquinol-1-yl) acetone hydrochloride. 3-acetyl-1:2:3:4:6:7-hexahydro 11 b [H] - 9:10 - dimethoxy - 2 - methylbenzo[a] - quinolizine-2-ol hydrochloride is prepared by sodium methoxide and hydrochloric acid cyclisation. 11:31-bis (2-butyryl-1:2:3:4-tetrahydro-6:7-dimethoxyisoquinol-1-yl) acetone is self condensed to form fractions which yield 3-ethyl-1:4:6:7 - tetrahydro - 9:10 - dimethoxy - 2 - (21 butyryl - 11:21:31:41 - tetrahydro - 61:71-dimethoxyisoquinol-11-yl) methyl-4-oxo-11(b)H-benzo [a] quinolizine and other quinolizines. The preparation of 3-Acetyl-1:4:6:7-tetrahydro-9:10 - dimethoxy - 2 - methyl - 11b[H]-benzo [a] quinolizine, 3-acetyl-1:2:3:4:6:7-hexahydro - 2 - hydroxy - 9,10 - dimethoxy - 2 - [11:21:31:41 tetrahydro-61-71-dimethoxy-21-(311 -oxobutyl) - isoquinol-11-yl] methyl-11b[H]-benzo-[a]-quinolizine, 3-acetyl-1:4:6:7-tetrahydro-9:10-dimethoxy - 2 - [11:21:31:41 - tetrahydro - 61,71 - dimethoxy 21 - (311 - oxobutyl) - isoquinol - 11-yl] methyl - 11b[H] - benzo[a] - quinolozine, and 6:7 - dimethoxy - 1,2,3,4 - tetrahydro - isoquinol - 1-yl-acetoacetic acid is also described.
Priority Applications (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2352259A GB960181A (en) | 1959-07-08 | 1959-07-08 | Substituted tetrahychroisoquinolines |
DK266060A DK105810C (en) | 1959-07-08 | 1960-07-07 | Process for the preparation of bis- (1,2,3,4-tetrahydroisoquinolinyl) -acetone compounds or salts thereof. |
BE592717A BE592717A (en) | 1959-07-08 | 1960-07-07 | Compounds of the isoquinoline series and their preparation. |
CH775360A CH487159A (en) | 1959-07-08 | 1960-07-07 | Process for the preparation of substituted 1,2,3,4-tetrahydroisoquinolines |
DK371061A DK109517C (en) | 1959-07-08 | 1960-07-07 | Process for the preparation of benzoquinolizine compounds or acid addition salts thereof. |
CH1794365A CH479587A (en) | 1959-07-08 | 1960-07-07 | Process for the preparation of benzoquinolizines |
DK496064A DK109448C (en) | 1959-07-08 | 1960-07-07 | Process for the preparation of benzoquinolizine compounds or acid addition salts thereof. |
DK508164A DK109835C (en) | 1959-07-08 | 1960-07-07 | Process for the preparation of 1,2,3,4-tetrahydroisoquinoline compounds or salts thereof. |
DE19601445062 DE1445062A1 (en) | 1959-07-08 | 1960-07-08 | Optionally substituted benzoquinolizines and processes for their preparation |
SE668960A SE310677B (en) | 1959-07-08 | 1960-07-08 | |
DE19601445051 DE1445051A1 (en) | 1959-07-08 | 1960-07-08 | Tetrahydroisoquinoline derivatives and processes for their preparation |
NL6811774A NL6811774A (en) | 1959-07-08 | 1968-08-19 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2352259A GB960181A (en) | 1959-07-08 | 1959-07-08 | Substituted tetrahychroisoquinolines |
Publications (1)
Publication Number | Publication Date |
---|---|
GB960181A true GB960181A (en) | 1964-06-10 |
Family
ID=10196995
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2352259A Expired GB960181A (en) | 1959-07-08 | 1959-07-08 | Substituted tetrahychroisoquinolines |
Country Status (7)
Country | Link |
---|---|
BE (1) | BE592717A (en) |
CH (1) | CH487159A (en) |
DE (2) | DE1445062A1 (en) |
DK (4) | DK109835C (en) |
GB (1) | GB960181A (en) |
NL (1) | NL6811774A (en) |
SE (1) | SE310677B (en) |
-
1959
- 1959-07-08 GB GB2352259A patent/GB960181A/en not_active Expired
-
1960
- 1960-07-07 DK DK508164A patent/DK109835C/en active
- 1960-07-07 DK DK266060A patent/DK105810C/en active
- 1960-07-07 DK DK371061A patent/DK109517C/en active
- 1960-07-07 BE BE592717A patent/BE592717A/en unknown
- 1960-07-07 DK DK496064A patent/DK109448C/en active
- 1960-07-07 CH CH775360A patent/CH487159A/en not_active IP Right Cessation
- 1960-07-08 SE SE668960A patent/SE310677B/xx unknown
- 1960-07-08 DE DE19601445062 patent/DE1445062A1/en active Pending
- 1960-07-08 DE DE19601445051 patent/DE1445051A1/en active Pending
-
1968
- 1968-08-19 NL NL6811774A patent/NL6811774A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
DK109448C (en) | 1968-04-29 |
SE310677B (en) | 1969-05-12 |
DK109517C (en) | 1968-05-06 |
DK105810C (en) | 1966-11-14 |
BE592717A (en) | 1960-10-31 |
DK109835C (en) | 1968-07-15 |
DE1445062A1 (en) | 1969-01-09 |
NL6811774A (en) | 1968-10-25 |
DE1445051A1 (en) | 1968-10-17 |
CH487159A (en) | 1970-03-15 |
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