JPS5967290A - ピリドベンズオキサジン誘導体の製法 - Google Patents
ピリドベンズオキサジン誘導体の製法Info
- Publication number
- JPS5967290A JPS5967290A JP17674582A JP17674582A JPS5967290A JP S5967290 A JPS5967290 A JP S5967290A JP 17674582 A JP17674582 A JP 17674582A JP 17674582 A JP17674582 A JP 17674582A JP S5967290 A JPS5967290 A JP S5967290A
- Authority
- JP
- Japan
- Prior art keywords
- boron trifluoride
- methyl
- complex
- pyrido
- dihydro
- 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.)
- Granted
Links
- QDEJGQKJMKXYLM-UHFFFAOYSA-N 2h-pyrido[2,3-h][1,2]benzoxazine Chemical compound C1=CC2=NC=CC=C2C2=C1C=CNO2 QDEJGQKJMKXYLM-UHFFFAOYSA-N 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims description 6
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract description 22
- 229910015900 BF3 Inorganic materials 0.000 abstract description 11
- 239000002253 acid Substances 0.000 abstract description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 239000004599 antimicrobial Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000013078 crystal Substances 0.000 description 13
- 239000013522 chelant Substances 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- XNIVKSPSCYJKBL-UHFFFAOYSA-N 2h-1,2-benzoxazine-6-carboxylic acid Chemical compound O1NC=CC2=CC(C(=O)O)=CC=C21 XNIVKSPSCYJKBL-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- CHNLPLHJUPMEOI-UHFFFAOYSA-N oxolane;trifluoroborane Chemical compound FB(F)F.C1CCOC1 CHNLPLHJUPMEOI-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- CFLBIADORGSMCX-UHFFFAOYSA-N 2h-1,4-benzoxazine-6-carboxylic acid Chemical compound O1CC=NC2=CC(C(=O)O)=CC=C21 CFLBIADORGSMCX-UHFFFAOYSA-N 0.000 description 1
- RROQSCBOBBLOOA-UHFFFAOYSA-N C(C)OC(=O)C=1C=CC2=C(C=CNO2)C1 Chemical compound C(C)OC(=O)C=1C=CC2=C(C=CNO2)C1 RROQSCBOBBLOOA-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17674582A JPS5967290A (ja) | 1982-10-07 | 1982-10-07 | ピリドベンズオキサジン誘導体の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17674582A JPS5967290A (ja) | 1982-10-07 | 1982-10-07 | ピリドベンズオキサジン誘導体の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5967290A true JPS5967290A (ja) | 1984-04-16 |
| JPH0149272B2 JPH0149272B2 (enrdf_load_stackoverflow) | 1989-10-24 |
Family
ID=16019057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17674582A Granted JPS5967290A (ja) | 1982-10-07 | 1982-10-07 | ピリドベンズオキサジン誘導体の製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5967290A (enrdf_load_stackoverflow) |
-
1982
- 1982-10-07 JP JP17674582A patent/JPS5967290A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0149272B2 (enrdf_load_stackoverflow) | 1989-10-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HU215429B (hu) | Eljárás ((6,7-helyettesített-8-alkoxi-1-ciklopropil-1,4-dihidro-4-oxo-3-kinolin-karbonsav)-O3,O4-)bisz(acil-oxi)-borát-származékok előállítására | |
| AU602529B2 (en) | New compounds, processes for their preparation and their use | |
| JPH0240066B2 (enrdf_load_stackoverflow) | ||
| JPS591489A (ja) | ピリドベンゾオキサジン誘導体 | |
| JPS5967290A (ja) | ピリドベンズオキサジン誘導体の製法 | |
| JPS62255482A (ja) | ６−アルコキシキノロンカルボン酸誘導体 | |
| JPH0116837B2 (enrdf_load_stackoverflow) | ||
| Kojima et al. | Synthesis of indolizines and pyrrolo [2, 1‐b] azoles from 2‐pyridylmagnesium bromide and 2‐lithiated azoles using tris (alkylthio)‐cyclopropenyl cations as a three‐carbon building block | |
| JPH04169583A (ja) | フェノチアジン誘導体およびその製造方法 | |
| JPS6011913B2 (ja) | １，８−ナフチリジン誘導体ならびにその製造方法 | |
| FI86185B (fi) | Amifloxacinmellanprodukt och foerfarande foer dess framstaellning. | |
| JPH0372073B2 (enrdf_load_stackoverflow) | ||
| JPH0148910B2 (enrdf_load_stackoverflow) | ||
| JPH0215554B2 (enrdf_load_stackoverflow) | ||
| JPH0475239B2 (enrdf_load_stackoverflow) | ||
| EP0170214B1 (en) | The preparation of 1,3-dihydro-4-pyridoyl-2h-imidazol-2-ones | |
| JPS59122493A (ja) | ピリドベンズオキサジン誘導体の製法 | |
| Cymerman Craig et al. | Chiroptical properties of pelletierine and anaferine | |
| Daneshtalab et al. | Studies on reactive intermediates. Part I. An approach to the synthesis of 2‐phenyl‐7‐carbethoxy‐5H‐1, 3, 4‐thiadiazolo [2, 3‐a] pyrimidin‐5‐one | |
| JPH0214356B2 (enrdf_load_stackoverflow) | ||
| JPS62294689A (ja) | キノリン−３−カルボン酸誘導体 | |
| JPH0150709B2 (enrdf_load_stackoverflow) | ||
| JPS59216890A (ja) | ピリドベンズオキサジン誘導体の製法 | |
| JPH0332552B2 (enrdf_load_stackoverflow) | ||
| KR900001079B1 (ko) | 퀴놀론 유도체의 제조방법 |