CH642660A5 - Process for the preparation of enones of the narwedine type and their derivatives - Google Patents
Process for the preparation of enones of the narwedine type and their derivatives Download PDFInfo
- Publication number
- CH642660A5 CH642660A5 CH978279A CH978279A CH642660A5 CH 642660 A5 CH642660 A5 CH 642660A5 CH 978279 A CH978279 A CH 978279A CH 978279 A CH978279 A CH 978279A CH 642660 A5 CH642660 A5 CH 642660A5
- Authority
- CH
- Switzerland
- Prior art keywords
- enones
- derivatives
- preparation
- type
- alkyl group
- 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 6
- 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 6
- 238000002360 preparation method Methods 0.000 title description 2
- 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
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000006056 electrooxidation reaction Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910019785 NBF4 Inorganic materials 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical class OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 241000234270 Amaryllidaceae Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229930013930 alkaloid Natural products 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000015320 potassium carbonate Nutrition 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
- AAUHVTGFRGYZDL-UHFFFAOYSA-N CNC(C1=C(C(=C(C(=C1)OC)OC)CCC1=CC=C(C=C1)OCC1=CC=CC=C1)Br)=O Chemical compound CNC(C1=C(C(=C(C(=C1)OC)OC)CCC1=CC=C(C=C1)OCC1=CC=CC=C1)Br)=O AAUHVTGFRGYZDL-UHFFFAOYSA-N 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
- 229910020939 NaC104 Inorganic materials 0.000 description 1
- -1 NaHCOs 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
- 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
- 150000007522 mineralic acids Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical group 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
- 229910000029 sodium carbonate Inorganic materials 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)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BG7841458A BG28325A1 (en) | 1978-11-21 | 1978-11-21 | Method of obtaining of enons navedine type and their derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH642660A5 true CH642660A5 (en) | 1984-04-30 |
Family
ID=3905326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH978279A CH642660A5 (en) | 1978-11-21 | 1979-10-31 | Process for the preparation of enones of the narwedine type and their derivatives |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS55107790A (it) |
| BG (1) | BG28325A1 (it) |
| CH (1) | CH642660A5 (it) |
| DD (1) | DD161094A3 (it) |
| DE (1) | DE2945161A1 (it) |
| FR (1) | FR2442230A1 (it) |
| IT (1) | IT1164751B (it) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SK283877B6 (sk) * | 1994-10-21 | 2004-04-06 | Sanochemia Pharmazeutika Ag | Spôsob výroby derivátov 4a,5,9,10,11,12,-hexahydro-6H- benzofuro[3a,3,2-ef][2]benzazepínu |
| US6407229B1 (en) | 1994-10-21 | 2002-06-18 | Sanochemia Pharmazeutika Ag | Processes for the preparation of derivatives of 4a,5,9,10,11,12-hexahydro-6H-benzofuro-[3a,3,2-ef][2] benzazapine |
| WO2005030713A2 (en) * | 2003-09-26 | 2005-04-07 | George Schloemer | Resolution of a narwedine amide derivative |
-
1978
- 1978-11-21 BG BG7841458A patent/BG28325A1/xx unknown
-
1979
- 1979-10-04 DD DD79216089A patent/DD161094A3/de not_active IP Right Cessation
- 1979-10-31 CH CH978279A patent/CH642660A5/de not_active IP Right Cessation
- 1979-11-07 IT IT50771/79A patent/IT1164751B/it active
- 1979-11-08 DE DE19792945161 patent/DE2945161A1/de not_active Withdrawn
- 1979-11-16 FR FR7928372A patent/FR2442230A1/fr active Pending
- 1979-11-21 JP JP15129979A patent/JPS55107790A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BG28325A1 (en) | 1980-04-15 |
| JPS55107790A (en) | 1980-08-19 |
| IT1164751B (it) | 1987-04-15 |
| FR2442230A1 (fr) | 1980-06-20 |
| IT7950771A0 (it) | 1979-11-07 |
| DE2945161A1 (de) | 1980-06-04 |
| DD161094A3 (de) | 1984-10-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0060437A1 (de) | Elektrochemisches Verfahren zur Herstellung von Benzanthronen und planaren polycyclischen aromatischen Oxyverbindungen | |
| DE2920562C2 (it) | ||
| CH642660A5 (en) | Process for the preparation of enones of the narwedine type and their derivatives | |
| DE1770579A1 (de) | Verfahren zur Herstellung von Rifamycin | |
| DE2623055A1 (de) | Platierungsbad zur elektroplatierung von nickel | |
| CH642633A5 (en) | Process for the preparation of dienones of the narwedine type and their derivatives | |
| DE1768584A1 (de) | Verfahren zur elektrolytischen Hydrodimerisation | |
| DE2948999C2 (de) | Wässriges, saures Bad zur galvanischen Abscheidung von Gold und Verfahren zur galvanischen Abscheidung von Hartgold unter seiner Verwendung | |
| DE2720425A1 (de) | Verfahren zur herstellung eines gemisches eines gegebenenfalls durch einen inerten rest substituierten 4-hydroxymethylimidazols mit einem 4-nieder-alkoxymethylimidazol | |
| DE1668151C3 (de) | Verfahren zur Herstellung von Dimethylsulfoxid | |
| DE194038C (it) | ||
| DE415318C (de) | Verfahren zur Herstellung von 4-Arylamino-1-arylimino-2-naphthochinonen | |
| DE1815788A1 (de) | 4,5-substituierte N-Oxy- und Hydroxyhydoimidazole | |
| EP0221022A2 (de) | Verfahren zur Herstellung von 5-Nitro-1,4-naphthochinonen | |
| DE2328196C3 (de) | Verfahren zur Herstellung von Sulfonen | |
| DE1695261C3 (de) | Verfahren zur Herstellung von N,N"disubstituiertenBipyridyliumsalzen | |
| DE601642C (de) | Verfahren zur Herstellung von Disulfiden | |
| DD203537A1 (de) | Verfahren zur herstellung von 2-alkyl (bzw. aryl)thio-3-acyl-acrylsaeuren | |
| AT281788B (de) | Verfahren zur Herstellung von Methylolalkansäuren | |
| DE1768130C3 (de) | lsocyan-diphenyl(-thio)-äther sowie Verfahren zu ihrer Herstellung und deren Verwendung zur Bekämpfung von Akariden | |
| DE1695343A1 (de) | Verfahren zur Herstellung von Purinderivaten | |
| DE2350395C3 (de) | N-(m-Trifluormethylthiophenyl)-piperazin, deren Salze, Verfahren zu deren Herstellung und deren Verwendung als Zwischenverbindung zur Herstellung von Piperazin-Derivaten | |
| DE3405059A1 (de) | Katalytische anode mit bleibasis, verfahren zu deren herstellung und ihre verwendung | |
| DE3409185C2 (it) | ||
| AT224239B (de) | Verfahren zur Herstellung neuer Pigmente bzw. neuer Küpenfarbstoffe |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |