ES262676A1 - Benzo(a)quinolizine derivatives and method for making them - Google Patents
Benzo(a)quinolizine derivatives and method for making themInfo
- Publication number
- ES262676A1 ES262676A1 ES0262676A ES262676A ES262676A1 ES 262676 A1 ES262676 A1 ES 262676A1 ES 0262676 A ES0262676 A ES 0262676A ES 262676 A ES262676 A ES 262676A ES 262676 A1 ES262676 A1 ES 262676A1
- Authority
- ES
- Spain
- Prior art keywords
- group
- benzo
- making
- compounds
- lower alkoxy
- 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
- 238000000034 method Methods 0.000 title abstract 2
- RMOYSWDTCQZJGS-UHFFFAOYSA-N 6h-benzo[a]quinolizine Chemical class C1=CC=CN2CC=C(C=CC=C3)C3=C21 RMOYSWDTCQZJGS-UHFFFAOYSA-N 0.000 title 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- SSSYOIPHXANRMO-UHFFFAOYSA-N 4h-benzo[a]quinolizine Chemical class C1=CC=C2C3=CC=CCN3C=CC2=C1 SSSYOIPHXANRMO-UHFFFAOYSA-N 0.000 abstract 1
- MBYXEBXZARTUSS-QLWBXOBMSA-N Emetamine Natural products O(C)c1c(OC)cc2c(c(C[C@@H]3[C@H](CC)CN4[C@H](c5c(cc(OC)c(OC)c5)CC4)C3)ncc2)c1 MBYXEBXZARTUSS-QLWBXOBMSA-N 0.000 abstract 1
- AUVVAXYIELKVAI-UHFFFAOYSA-N SJ000285215 Natural products N1CCC2=CC(OC)=C(OC)C=C2C1CC1CC2C3=CC(OC)=C(OC)C=C3CCN2CC1CC AUVVAXYIELKVAI-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- AUVVAXYIELKVAI-CKBKHPSWSA-N emetine Chemical compound N1CCC2=CC(OC)=C(OC)C=C2[C@H]1C[C@H]1C[C@H]2C3=CC(OC)=C(OC)C=C3CCN2C[C@@H]1CC AUVVAXYIELKVAI-CKBKHPSWSA-N 0.000 abstract 1
- 229960002694 emetine Drugs 0.000 abstract 1
- AUVVAXYIELKVAI-UWBTVBNJSA-N emetine Natural products N1CCC2=CC(OC)=C(OC)C=C2[C@H]1C[C@H]1C[C@H]2C3=CC(OC)=C(OC)C=C3CCN2C[C@H]1CC AUVVAXYIELKVAI-UWBTVBNJSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention comprises benzoquinolizine compounds of the general formula <FORM:0999091/C2/1> and their optical enantiomorphs, wherein R1 is an alkyl group of from one to four carbon atoms, R2 is a lower alkoxy or a hydroxy group, and R3 and R4 are methyl or ethyl groups or together form a methylene group, together with a process for their preparation by condensing a ketone of formula <FORM:0999091/C2/2> with a (lower alkoxycarbonylmethylene)triarylphosphorane to give a compound of the above formula in which R2 is a lower alkoxy group, and if desired hydrolysing the product to yield the corresponding acid. The compounds are useful as intermediates for the synthesis of emetine. to. Specifications 999,092 and 999,096 are referred
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3993459A GB999091A (en) | 1959-11-24 | 1959-11-24 | Benzo(a)quinolizine derivatives and method for making them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES262676A1 true ES262676A1 (en) | 1961-04-16 |
Family
ID=10412290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0262676A Expired ES262676A1 (en) | 1959-11-24 | 1960-11-23 | Benzo(a)quinolizine derivatives and method for making them |
Country Status (7)
| Country | Link |
|---|---|
| CH (1) | CH409969A (en) |
| CS (1) | CS161683B2 (en) |
| ES (1) | ES262676A1 (en) |
| FI (1) | FI41401B (en) |
| GB (1) | GB999091A (en) |
| LU (1) | LU39451A1 (en) |
| MC (1) | MC247A1 (en) |
-
1959
- 1959-11-24 GB GB3993459A patent/GB999091A/en not_active Expired
-
1960
- 1960-11-22 CH CH1308460A patent/CH409969A/en unknown
- 1960-11-22 MC MC275A patent/MC247A1/en unknown
- 1960-11-23 CS CS703860A patent/CS161683B2/cs unknown
- 1960-11-23 FI FI193960A patent/FI41401B/fi active
- 1960-11-23 ES ES0262676A patent/ES262676A1/en not_active Expired
- 1960-11-24 LU LU39451D patent/LU39451A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB999091A (en) | 1965-07-21 |
| CS161683B2 (en) | 1975-06-10 |
| MC247A1 (en) | 1961-06-15 |
| CH409969A (en) | 1966-03-31 |
| LU39451A1 (en) | 1961-05-24 |
| FI41401B (en) | 1969-07-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES262677A1 (en) | Method for making benzo(a)quinolizine derivatives | |
| ES8206509A1 (en) | Reactive derivatives of 3-oxa-bicyclo(4.3.0)-non-1-ene-9-one, process for their preparation and their use. | |
| GB1095894A (en) | Substituted indolizines and preparation thereof | |
| NO883080D0 (en) | PROCEDURE FOR THE MANUFACTURE OF NEW CEFEM COMPOUNDS. | |
| GB999091A (en) | Benzo(a)quinolizine derivatives and method for making them | |
| GB815279A (en) | Novel benzomorpholone derivatives and a process for the manufacture thereof | |
| GB858792A (en) | New pyridazine derivatives and processes for their manufacture | |
| GB532822A (en) | Improvements in and relating to the production of ª‡-coumarilyl and ª‡-thionaphthenoyl-acetic acid esters | |
| SE7510787L (en) | NEW NITROGENIC, POLYCYCLIC ASSOCIATIONS, SALTS THEREOF AND THEIR OPTICAL ANTIPODS, JUST LIKE THEIR PREPARATION | |
| US2537893A (en) | 2-carboalkoxy-3-keto-4-acylamido-tetrahydrothiophene | |
| GB1298620A (en) | Substituted benzopyrans and process for the production thereof | |
| GB859716A (en) | New pyrimidines and their salts and a process for their production | |
| ES432738A1 (en) | PROCEDURE TO PRODUCE CEPHALOSPORINS AND ANALOGS. | |
| GB793722A (en) | Novel phosphates and a process for the manufacture thereof | |
| GB1067627A (en) | 3-(ªamino-ª-hydroxypropyl)-4-alkyl-7-hydroxy-coumarin derivatives and process for their production | |
| SE7909157L (en) | PROCEDURE FOR THE PREPARATION OF CYCLE-1,3,2-OXAZAPHOSPHORPHYL DERIVATIVES | |
| GB1042205A (en) | Manufacture of benzo[a]quinolizines | |
| NO152132C (en) | PROCEDURE FOR THE PREPARATION OF CARBZOLD DERIVATIVES | |
| GB1064524A (en) | Process for preparing new isophthalic acid derivatives | |
| SE7900889L (en) | WAY TO PRODUCE XANTONE DERIVATIVES | |
| GB948080A (en) | Benzopyranone derivatives and processes for their production | |
| GB1290361A (en) | ||
| GB1024650A (en) | Benzofuran derivatives and process for their production | |
| JPS51146490A (en) | Process for preparing penicillanic acid ester 1-oxide derivatives | |
| GB889033A (en) | Process for the production of substituted 3:5-diketopyrazolidines, and intermediate compounds obtained therein |