CH642633A5 - Process for the preparation of dienones of the narwedine type and their derivatives - Google Patents
Process for the preparation of dienones of the narwedine type and their derivatives Download PDFInfo
- Publication number
- CH642633A5 CH642633A5 CH978179A CH978179A CH642633A5 CH 642633 A5 CH642633 A5 CH 642633A5 CH 978179 A CH978179 A CH 978179A CH 978179 A CH978179 A CH 978179A CH 642633 A5 CH642633 A5 CH 642633A5
- Authority
- CH
- Switzerland
- Prior art keywords
- derivatives
- dienones
- preparation
- alkyl group
- lower alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- QENVUHCAYXAROT-UHFFFAOYSA-N Galanthaminon Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(=O)C=C2 QENVUHCAYXAROT-UHFFFAOYSA-N 0.000 title claims description 5
- QENVUHCAYXAROT-YOEHRIQHSA-N Narwedine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1CC(=O)C=C2 QENVUHCAYXAROT-YOEHRIQHSA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- WCRYNEMFWLZAAZ-WMLDXEAASA-N Narwedine Natural products COc1ccc2CCCC[C@@]34C=CC(=O)C[C@@H]3Oc1c24 WCRYNEMFWLZAAZ-WMLDXEAASA-N 0.000 title 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical class OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 238000006056 electrooxidation reaction Methods 0.000 claims description 4
- 229910013462 LiC104 Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 241000234270 Amaryllidaceae Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- -1 KC104 Inorganic materials 0.000 description 2
- 229930013930 alkaloid Natural products 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910004039 HBF4 Inorganic materials 0.000 description 1
- 229910019785 NBF4 Inorganic materials 0.000 description 1
- 229910020939 NaC104 Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/23—Oxidation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BG7842315A BG28324A2 (en) | 1978-11-21 | 1978-11-21 | Method of obtaining of dienons navedine type and their derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH642633A5 true CH642633A5 (en) | 1984-04-30 |
Family
ID=3905594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH978179A CH642633A5 (en) | 1978-11-21 | 1979-10-31 | Process for the preparation of dienones of the narwedine type and their derivatives |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS55105669A (fr) |
| BG (1) | BG28324A2 (fr) |
| CH (1) | CH642633A5 (fr) |
| DD (1) | DD160866A3 (fr) |
| DE (1) | DE2945162A1 (fr) |
| FR (1) | FR2442237A1 (fr) |
| IT (1) | IT1164750B (fr) |
| PL (1) | PL219581A1 (fr) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3950236A (en) * | 1974-07-24 | 1976-04-13 | The United States Of America As Represented By The Secretary Of Health, Education And Welfare | Production of angular alkylated polycyclides by electrochemical annelation |
-
1978
- 1978-11-21 BG BG7842315A patent/BG28324A2/xx unknown
-
1979
- 1979-10-04 DD DD79216088A patent/DD160866A3/de not_active IP Right Cessation
- 1979-10-31 CH CH978179A patent/CH642633A5/de not_active IP Right Cessation
- 1979-11-07 IT IT50770/79A patent/IT1164750B/it active
- 1979-11-08 DE DE19792945162 patent/DE2945162A1/de not_active Withdrawn
- 1979-11-13 PL PL21958179A patent/PL219581A1/xx unknown
- 1979-11-16 FR FR7928373A patent/FR2442237A1/fr active Granted
- 1979-11-21 JP JP15130079A patent/JPS55105669A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DD160866A3 (de) | 1984-05-16 |
| IT7950770A0 (it) | 1979-11-07 |
| JPS55105669A (en) | 1980-08-13 |
| FR2442237B1 (fr) | 1983-12-02 |
| PL219581A1 (fr) | 1980-07-28 |
| DE2945162A1 (de) | 1980-06-04 |
| BG28324A2 (en) | 1980-04-15 |
| IT1164750B (it) | 1987-04-15 |
| FR2442237A1 (fr) | 1980-06-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |