ES434406A1 - Octahydrobenzo(c)(1,6)naphthyridines - Google Patents
Octahydrobenzo(c)(1,6)naphthyridinesInfo
- Publication number
- ES434406A1 ES434406A1 ES434406A ES434406A ES434406A1 ES 434406 A1 ES434406 A1 ES 434406A1 ES 434406 A ES434406 A ES 434406A ES 434406 A ES434406 A ES 434406A ES 434406 A1 ES434406 A1 ES 434406A1
- Authority
- ES
- Spain
- Prior art keywords
- carbon atoms
- alkoxy
- benzyloxy
- hydroxy
- hydrogen
- 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
- 150000005054 naphthyridines Chemical class 0.000 title abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 13
- 125000003545 alkoxy group Chemical group 0.000 abstract 9
- 229910052739 hydrogen Inorganic materials 0.000 abstract 7
- 239000001257 hydrogen Substances 0.000 abstract 7
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- SWJXWSAKHXBQSY-UHFFFAOYSA-N benzo(c)cinnoline Chemical compound C1=CC=C2C3=CC=CC=C3N=NC2=C1 SWJXWSAKHXBQSY-UHFFFAOYSA-N 0.000 abstract 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 4
- -1 benzyloxy, hydroxy Chemical group 0.000 abstract 4
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000005661 deetherification reaction Methods 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 239000002841 Lewis acid Substances 0.000 abstract 1
- BJVCSICIEDHBNI-UHFFFAOYSA-N benzo[b][1,8]naphthyridine Chemical group N1=CC=CC2=CC3=CC=CC=C3N=C21 BJVCSICIEDHBNI-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Procedure for preparing naphthyridine derivatives of formula I **(See formula)** wherein the radical indicated in position 8 or 9 of the benzonaphthyridine structure (R1) is hydrogen, alkoxy of 1 to 4 carbon atoms or hydroxy, and (i) R2 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, benzyloxy, hydroxy, halogen, nitro, amino, dimethylamino, or -NHCOR5, where R5 is hydrogen or alkyl of 1 to 4 carbon atoms, and R3 and R4 are hydrogen, or (ii) R2 is alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, benzyloxy, hydroxy, halogen or nitro, R3 is alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, benzyloxy, hydroxy or chloro, and R4 is hydrogen, (iii) R2, R3 and R4, independently, are alkoxy of 1 to 4 carbon atoms or benzyloxy, or (iv) R2, R3 and R4, independently, are alkyl of 1 to 4 4 carbon atoms, or (v) R2, R3 and R4 are hydroxy, provided that (i) when one of the radicals R2, R3 and R4 is benzyloxy, the radical indicated in position 8 or 9 of the is The structure of benzonaphthyridine (R1) is hydrogen or alkoxy of 1 to 4 carbon atoms, (ii) when the radical indicated in position 8 or 9 of the benzonaphthyridine (R1) structure has a meaning other than hydrogen or alkoxy and is found at position 9, each of the radicals R2, R3 and R4 has a meaning other than alkoxy of 1 to 4 carbon atoms, and (iii) when one of the radicals R2 and R3 is benzyloxy or alkoxy of 1 to 4 4 carbon atoms, the remaining radical R2 or R3 has a meaning other than hydroxy, characterized in that: a compound of formula III is treated, **(See formula)** wherein R2, R3 and R4 have the meanings indicated above with the aforementioned condition, and R7 is an ether radical capable of being cleaved under the reaction conditions to form a hydroxy radical, under the conditions of an ether cleavage, to produce a compound of formula Ia, **(See formula)** wherein R2, R3 and R4 have the meanings indicated above with the aforementioned condition and with the additional condition that (iv) each of R2, R3 and R4 has a meaning other than benzyloxy; the ether cleavage being carried out with a Lewis acid, preferably in an inert organic solvent, at temperatures of approximately -80 to + 70ºC. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH155074 | 1974-02-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES434406A1 true ES434406A1 (en) | 1977-03-01 |
Family
ID=4213026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES434406A Expired ES434406A1 (en) | 1974-02-05 | 1975-02-03 | Octahydrobenzo(c)(1,6)naphthyridines |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS50108297A (en) |
| AT (1) | AT351536B (en) |
| BE (1) | BE825124A (en) |
| CA (1) | CA1055944A (en) |
| DD (1) | DD117216A5 (en) |
| DE (1) | DE2503156A1 (en) |
| DK (1) | DK136189B (en) |
| ES (1) | ES434406A1 (en) |
| FI (1) | FI750205A7 (en) |
| FR (1) | FR2259611B1 (en) |
| GB (2) | GB1497723A (en) |
| HU (1) | HU169923B (en) |
| IL (1) | IL46553A (en) |
| NL (1) | NL7501159A (en) |
| NO (1) | NO750263L (en) |
| NZ (1) | NZ176550A (en) |
| PH (1) | PH11824A (en) |
| SE (1) | SE7500859L (en) |
| ZA (1) | ZA75743B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8800397D0 (en) * | 1988-01-08 | 1988-02-10 | Sandoz Ltd | Improvements in/relating to organic compounds |
| MY105344A (en) * | 1990-05-16 | 1994-09-30 | Byk Gulden Lomberg Chemische Fabrik | New sulphonyl compounds |
-
1975
- 1975-01-27 SE SE7500859A patent/SE7500859L/xx unknown
- 1975-01-27 FI FI750205A patent/FI750205A7/fi not_active Application Discontinuation
- 1975-01-27 DE DE19752503156 patent/DE2503156A1/en active Pending
- 1975-01-27 DK DK24275AA patent/DK136189B/en unknown
- 1975-01-29 NO NO750263A patent/NO750263L/no unknown
- 1975-01-31 NL NL7501159A patent/NL7501159A/en not_active Application Discontinuation
- 1975-02-03 ES ES434406A patent/ES434406A1/en not_active Expired
- 1975-02-03 PH PH16771A patent/PH11824A/en unknown
- 1975-02-03 GB GB30857/77A patent/GB1497723A/en not_active Expired
- 1975-02-03 HU HUSA2741A patent/HU169923B/hu unknown
- 1975-02-03 NZ NZ176550A patent/NZ176550A/en unknown
- 1975-02-03 DD DD183969A patent/DD117216A5/xx unknown
- 1975-02-03 IL IL46553A patent/IL46553A/en unknown
- 1975-02-03 GB GB4516/75A patent/GB1497722A/en not_active Expired
- 1975-02-03 BE BE153007A patent/BE825124A/en unknown
- 1975-02-04 JP JP50014021A patent/JPS50108297A/ja active Pending
- 1975-02-04 AT AT79975A patent/AT351536B/en not_active IP Right Cessation
- 1975-02-04 CA CA219,303A patent/CA1055944A/en not_active Expired
- 1975-02-05 FR FR7503547A patent/FR2259611B1/fr not_active Expired
- 1975-02-05 ZA ZA00750743A patent/ZA75743B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL46553A (en) | 1977-12-30 |
| SE7500859L (en) | 1975-08-06 |
| IL46553A0 (en) | 1975-04-25 |
| NO750263L (en) | 1975-09-01 |
| ATA79975A (en) | 1979-01-15 |
| BE825124A (en) | 1975-08-04 |
| NL7501159A (en) | 1975-08-07 |
| ZA75743B (en) | 1976-09-29 |
| FR2259611B1 (en) | 1980-01-11 |
| DK136189B (en) | 1977-08-29 |
| DE2503156A1 (en) | 1975-08-07 |
| FI750205A7 (en) | 1975-08-06 |
| DD117216A5 (en) | 1976-01-05 |
| JPS50108297A (en) | 1975-08-26 |
| GB1497722A (en) | 1978-01-12 |
| AU7784375A (en) | 1976-08-05 |
| GB1497723A (en) | 1978-01-12 |
| CA1055944A (en) | 1979-06-05 |
| FR2259611A1 (en) | 1975-08-29 |
| AT351536B (en) | 1979-07-25 |
| NZ176550A (en) | 1978-09-25 |
| HU169923B (en) | 1977-02-28 |
| PH11824A (en) | 1978-07-19 |
| DK24275A (en) | 1975-09-29 |
| DK136189C (en) | 1978-01-30 |
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