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 PDF

Info

Publication number: CH642660A5
Authority: CH; Switzerland
Prior art keywords: enones; derivatives; preparation; type; alkyl group
Prior art date: 1978-11-21

Application number

CH978279A

Other languages

German (de)

English (en)

Inventor

Radoslav Vlachov

Dikran Krikorjan

Maria Sagorova

Maja Chinova

Paruschev Stojan

Original Assignee

Edinen Zentar Chim

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.)

1978-11-21

Filing date

1979-10-31

Publication date

1984-04-30

1979-10-31 Application filed by Edinen Zentar Chim filed Critical Edinen Zentar Chim

1984-04-30 Publication of CH642660A5 publication Critical patent/CH642660A5/de

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)
Crystals, And After-Treatments Of Crystals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

CH978279A 1978-11-21 1979-10-31 Process for the preparation of enones of the narwedine type and their derivatives CH642660A5 (en)

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)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES2106700T3 (es) *	1994-10-21	2000-05-16	Sanochemia Pharmazeutika Ag	Procedimiento para la preparacion de derivados de la 4a,5,9,10,11,12-hexahidro-6h-benzofuro(3a,3,2-ef)(2)benzacepinas.
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
US7307162B2 (en) *	2003-09-26	2007-12-11	Scinopharm Taiwan, Ltd.	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
IT7950771A0 (it)	1979-11-07
FR2442230A1 (fr)	1980-06-20
JPS55107790A (en)	1980-08-19
DD161094A3 (de)	1984-10-17
BG28325A1 (en)	1980-04-15
IT1164751B (it)	1987-04-15
DE2945161A1 (de)	1980-06-04

Legal Events

Date	Code	Title	Description
1987-06-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

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EP0022062A1 (de)	1981-01-07	Elektrochemisches Verfahren zur Herstellung von Benzanthron
DE2920562C2 (it)	1989-01-19
CH642660A5 (en)	1984-04-30	Process for the preparation of enones of the narwedine type and their derivatives
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CH642633A5 (en)	1984-04-30	Process for the preparation of dienones of the narwedine type and their derivatives
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DE1048569B (de)	1959-01-15	Verfahren zur Herstellung von Xanthendenvaten
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DE601642C (de)	1934-10-02	Verfahren zur Herstellung von Disulfiden
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DD203537A1 (de)	1983-10-26	Verfahren zur herstellung von 2-alkyl (bzw. aryl)thio-3-acyl-acrylsaeuren
AT281788B (de)	1970-06-10	Verfahren zur Herstellung von Methylolalkansäuren
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DE2350395C3 (de)	1980-08-28	N-(m-Trifluormethylthiophenyl)-piperazin, deren Salze, Verfahren zu deren Herstellung und deren Verwendung als Zwischenverbindung zur Herstellung von Piperazin-Derivaten
DE3405059A1 (de)	1984-08-16	Katalytische anode mit bleibasis, verfahren zu deren herstellung und ihre verwendung
DE3409185C2 (it)	1987-12-23
AT53153B (de)	1912-04-25	Verfahren zur elektrolytischen Herstellung von Ammoniumnitrat aus wasserhaltiger Salpetersäure.