GB912556A - New alkaloids and processes for their production - Google Patents
New alkaloids and processes for their productionInfo
- Publication number
- GB912556A GB912556A GB1576260A GB1576260A GB912556A GB 912556 A GB912556 A GB 912556A GB 1576260 A GB1576260 A GB 1576260A GB 1576260 A GB1576260 A GB 1576260A GB 912556 A GB912556 A GB 912556A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hexahydro
- berbine
- trimethoxy
- methoxycarbonyl
- formula
- 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
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
- C07D455/06—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine containing benzo [a] quinolizine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention comprises hexahydro-berbine compounds of the general formula:- <FORM:0912556/IV (b)/1> (in which R1 and R2 each represent an alkoxy group, R3 and R4 each represent an alkyl group having from one to six carbon atoms and R5 represents an acyl residue derived from an aliphatic, aromatic or araliphatic carboxylic acid), together with certain intermediates, viz. 2,3,11a -trimethoxy-10b -acetoxy-12b - methoxycarbonyl - 8aa ,9,10,11,12,12aa - hexahydro - 13 - dehydroberbine, 2,3,11a -trimethoxy - 10b - hydroxy-12b -methoxycarbonyl-8aa ,9,10,11,12, 12aa -hexahydro-14b -berbine and 2,3,11a - trimethoxy-10b -acetoxy-12b -methoxycarbonyl - 8aa ,9,10,11,12,12aa - hexahydro-14a -berbine, and their preparation by condensing an amine of formula:- <FORM:0912556/IV (b)/2> with an aldehyde of formula:- <FORM:0912556/IV (b)/3> reducing the resulting Schiff's base with a mixed hydride, e.g. sodium borohydride, heating the product to form a lactam, cyclizing the latter by dehydration, reducing the double bond of the resulting 13-dehydro-berbine compound with an acidic reducing agent, e.g. zinc/perchloric acid, and isolating the desired 14b -isomer of the hexahydroberbine compound preferably by fractional crystallisation. Specification 868,479 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR793913 | 1959-05-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB912556A true GB912556A (en) | 1962-12-12 |
Family
ID=8714467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1576260A Expired GB912556A (en) | 1959-05-05 | 1960-05-04 | New alkaloids and processes for their production |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH395102A (en) |
| GB (1) | GB912556A (en) |
| SE (1) | SE301807B (en) |
-
1960
- 1960-04-25 SE SE410660A patent/SE301807B/xx unknown
- 1960-04-26 CH CH475660A patent/CH395102A/en unknown
- 1960-05-04 GB GB1576260A patent/GB912556A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE301807B (en) | 1968-06-24 |
| CH395102A (en) | 1965-07-15 |
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