DE1108699B - Verfahren zur Herstellung von heterocyclischen Verbindungen mit der o-Chinon-Gruppierung - Google Patents
Verfahren zur Herstellung von heterocyclischen Verbindungen mit der o-Chinon-GruppierungInfo
- Publication number
- DE1108699B DE1108699B DEF29468A DEF0029468A DE1108699B DE 1108699 B DE1108699 B DE 1108699B DE F29468 A DEF29468 A DE F29468A DE F0029468 A DEF0029468 A DE F0029468A DE 1108699 B DE1108699 B DE 1108699B
- Authority
- DE
- Germany
- Prior art keywords
- heterocyclic compounds
- preparation
- dichloro
- quinolinequinone
- quinone group
- 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
- 238000000034 method Methods 0.000 title claims description 8
- 150000002391 heterocyclic compounds Chemical class 0.000 title claims description 5
- WOAHJDHKFWSLKE-UHFFFAOYSA-N 1,2-benzoquinone Chemical group O=C1C=CC=CC1=O WOAHJDHKFWSLKE-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- 125000003277 amino group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- -1 nitrogen-containing heterocyclic Compound Chemical class 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- TUWOPVCIIBKUQS-UHFFFAOYSA-N 6,7-dichloroquinoline-5,8-dione Chemical compound C1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=N1 TUWOPVCIIBKUQS-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 6
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- 230000003385 bacteriostatic effect Effects 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000009036 growth inhibition Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- SVPKNMBRVBMTLB-UHFFFAOYSA-N 2,3-dichloronaphthalene-1,4-dione Chemical class C1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=C1 SVPKNMBRVBMTLB-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- BCGVBGNZFXXWMK-UHFFFAOYSA-N 6,7-dichloro-2-methylquinoline-5,8-dione Chemical compound O=C1C(Cl)=C(Cl)C(=O)C2=NC(C)=CC=C21 BCGVBGNZFXXWMK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000295644 Staphylococcaceae Species 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 150000000182 1,3,5-triazines Chemical class 0.000 description 1
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- 229940005561 1,4-benzoquinone Drugs 0.000 description 1
- OUQMXTJYCAJLGO-UHFFFAOYSA-N 4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(N)=N1 OUQMXTJYCAJLGO-UHFFFAOYSA-N 0.000 description 1
- OQZMDDKDHRIGDY-UHFFFAOYSA-N 5-chloropyrimidin-2-amine Chemical compound NC1=NC=C(Cl)C=N1 OQZMDDKDHRIGDY-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 241001646725 Mycobacterium tuberculosis H37Rv Species 0.000 description 1
- 108700035964 Mycobacterium tuberculosis HsaD Proteins 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000006536 aerobic glycolysis Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- DGQLVPJVXFOQEV-JNVSTXMASA-N carminic acid Chemical compound OC1=C2C(=O)C=3C(C)=C(C(O)=O)C(O)=CC=3C(=O)C2=C(O)C(O)=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O DGQLVPJVXFOQEV-JNVSTXMASA-N 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000032823 cell division Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- 150000003584 thiosemicarbazones Chemical class 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Quinoline Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF29468A DE1108699B (de) | 1959-09-25 | 1959-09-25 | Verfahren zur Herstellung von heterocyclischen Verbindungen mit der o-Chinon-Gruppierung |
| CH989660A CH380738A (de) | 1959-09-25 | 1960-09-01 | Verfahren zur Herstellung von o-Chinonen |
| GB3233260A GB904680A (en) | 1959-09-25 | 1960-09-20 | Process for the production of o-quinones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF29468A DE1108699B (de) | 1959-09-25 | 1959-09-25 | Verfahren zur Herstellung von heterocyclischen Verbindungen mit der o-Chinon-Gruppierung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1108699B true DE1108699B (de) | 1961-06-15 |
| DE1108699C2 DE1108699C2 (enrdf_load_stackoverflow) | 1961-12-28 |
Family
ID=7093323
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF29468A Granted DE1108699B (de) | 1959-09-25 | 1959-09-25 | Verfahren zur Herstellung von heterocyclischen Verbindungen mit der o-Chinon-Gruppierung |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH380738A (enrdf_load_stackoverflow) |
| DE (1) | DE1108699B (enrdf_load_stackoverflow) |
| GB (1) | GB904680A (enrdf_load_stackoverflow) |
-
1959
- 1959-09-25 DE DEF29468A patent/DE1108699B/de active Granted
-
1960
- 1960-09-01 CH CH989660A patent/CH380738A/de unknown
- 1960-09-20 GB GB3233260A patent/GB904680A/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1108699C2 (enrdf_load_stackoverflow) | 1961-12-28 |
| CH380738A (de) | 1964-08-15 |
| GB904680A (en) | 1962-08-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1927473A1 (de) | Verfahren zur Herstellung von Phenazin-N,N-dioxiden | |
| DE1108699B (de) | Verfahren zur Herstellung von heterocyclischen Verbindungen mit der o-Chinon-Gruppierung | |
| DE1695974A1 (de) | Derivate des Pyrimidins | |
| DE1569603B2 (de) | Verfahren zur herstellung von oxazinfarbstoffen | |
| DE1445505B2 (de) | Im phenylkern substituierte 2-phenylamino-1,3-diazacyclopentene-(2) | |
| DE1643384A1 (de) | Algizide Mittel | |
| CH376115A (de) | Verfahren zur Herstellung neuer substituierter Pyrimidine | |
| DE2166270C3 (de) | Nicotinoylaminoäthansulfonyl-2amino-thiazol | |
| DE1445731B2 (de) | Halogenierte Chinoxalindenvate, Verfahren zu deren Herstellung und diese enthaltende fungizide Mittel | |
| DE2225433A1 (de) | Aminopyrazolo(3,4-b)pyridin-5-ketone mit ihren Salzen, Herstellungsverfahren dafür und Arzneimittel daraus | |
| DE1011424B (de) | Verfahren zur Herstellung von basisch substituierten 7-Alkyl-xanthinderivaten oder deren Salzen | |
| DE864555C (de) | Verfahren zur Herstellung von 2, 4-Diamino-5-aryloxypyrimidinen | |
| DE615184C (de) | Verfahren zur Darstellung von Aminoverbindungen der Chinolinreihe | |
| DE1445505C3 (de) | Im Phenylkern substituierte 2-Phenylamino-13-diazacyclopentene-(2) | |
| DE1000387C2 (de) | Verfahren zur Herstellung von neuen, in 9-Stellung substituierten 1, 10-Diazaanthracenen | |
| DE641598C (de) | Verfahren zur Darstellung heterocyclischer Verbindungen | |
| DE956306C (de) | Verfahren zur Herstellung von neuen Derivaten des Pyrimidins | |
| CH513158A (de) | Verfahren zur Herstellung von Pyrrolinverbindungen | |
| AT227683B (de) | Verfahren zur Herstellung von neuen Anthranilsäuren und deren Salzen | |
| DE1492069C3 (de) | N-Substituierte-m-aminophenole und deren Verwendung | |
| AT209345B (de) | Verfahren zur Herstellung von neuen, im Pyrazolkern substituierten Pyrazolo-pyrimidinen | |
| DE2242162A1 (de) | Neue pyrimidopyrimidinderivate und verfahren zu ihrer herstellung | |
| CH382181A (de) | Verfahren zur Herstellung neuer substituierter 3,3,3-Triphenylpropylamine | |
| DE953800C (de) | Verfahren zur Herstellung neuer Pyridazone | |
| DE1921340C3 (de) | In 4-Stellung substituierte 2-Phenyl-5-haIogen-pyrimidine |