SU470113A3 - Способ получени производных хинолина - Google Patents
Способ получени производных хинолинаInfo
- Publication number
- SU470113A3 SU470113A3 SU1157352A SU1157352A SU470113A3 SU 470113 A3 SU470113 A3 SU 470113A3 SU 1157352 A SU1157352 A SU 1157352A SU 1157352 A SU1157352 A SU 1157352A SU 470113 A3 SU470113 A3 SU 470113A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- ethoxy
- ethyl
- nitrophenoxy
- acid
- hydroxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title claims description 3
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title claims 2
- 239000000203 mixture Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- -1 2-methoxy-4-nitrophenoxy Chemical group 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 150000004702 methyl esters Chemical class 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- OCIAPZWEYCVROF-UHFFFAOYSA-N 1-decoxy-2-ethoxy-4-nitrobenzene Chemical compound CCCCCCCCCCOC1=CC=C([N+]([O-])=O)C=C1OCC OCIAPZWEYCVROF-UHFFFAOYSA-N 0.000 description 3
- BYRHXFSSWJPAFE-UHFFFAOYSA-N 2-(methoxymethylidene)propanedioic acid Chemical compound COC=C(C(O)=O)C(O)=O BYRHXFSSWJPAFE-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XBUXEBQYFNCXNA-UHFFFAOYSA-N 2-methoxy-4-nitro-1-nonoxybenzene Chemical compound COC1=C(OCCCCCCCCC)C=CC(=C1)[N+](=O)[O-] XBUXEBQYFNCXNA-UHFFFAOYSA-N 0.000 description 2
- ONGOCGYHKDHZCW-UHFFFAOYSA-N 2-methoxy-4-nitro-1-octoxybenzene Chemical compound COC1=C(OCCCCCCCC)C=CC(=C1)[N+](=O)[O-] ONGOCGYHKDHZCW-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GBGRBUIHAJELDD-UHFFFAOYSA-N 1-decoxy-2-methoxy-4-nitrobenzene Chemical compound COC1=C(OCCCCCCCCCC)C=CC(=C1)[N+](=O)[O-] GBGRBUIHAJELDD-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 description 1
- JKRIFKGKSXBJND-UHFFFAOYSA-N 3-methoxy-4-octoxyaniline Chemical compound CCCCCCCCOC1=CC=C(N)C=C1OC JKRIFKGKSXBJND-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QIJYXXLIQAPDIQ-UHFFFAOYSA-N 4-nitro-1-octoxy-2-propan-2-yloxybenzene Chemical compound C(C)(C)OC1=C(OCCCCCCCC)C=CC(=C1)[N+](=O)[O-] QIJYXXLIQAPDIQ-UHFFFAOYSA-N 0.000 description 1
- SDTGTOCGVUOCFA-UHFFFAOYSA-N C(CC)OC1=C(OCCCCCCCC)C=CC(=C1)[N+](=O)[O-] Chemical compound C(CC)OC1=C(OCCCCCCCC)C=CC(=C1)[N+](=O)[O-] SDTGTOCGVUOCFA-UHFFFAOYSA-N 0.000 description 1
- QSNPBHODEJJPNP-UHFFFAOYSA-N C(CCCCCCCCC)OC1=C(C=C(C=C1)[N+](=O)[O-])OCCCC Chemical compound C(CCCCCCCCC)OC1=C(C=C(C=C1)[N+](=O)[O-])OCCCC QSNPBHODEJJPNP-UHFFFAOYSA-N 0.000 description 1
- ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N N-undecane Natural products CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LWIWFCDNJNZEKB-UHFFFAOYSA-N dipropyl propanedioate Chemical compound CCCOC(=O)CC(=O)OCCC LWIWFCDNJNZEKB-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 229960000316 methyprylon Drugs 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229910000634 wood's metal Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2139666 | 1966-05-13 | ||
| GB35037/66A GB1168801A (en) | 1966-05-13 | 1966-08-04 | Quinoline Derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU470113A3 true SU470113A3 (ru) | 1975-05-05 |
Family
ID=26255310
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1157352A SU470113A3 (ru) | 1966-05-13 | 1967-05-13 | Способ получени производных хинолина |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3544686A (enExample) |
| AT (3) | AT278803B (enExample) |
| BE (1) | BE698305A (enExample) |
| CH (2) | CH477443A (enExample) |
| CS (1) | CS170120B2 (enExample) |
| DE (1) | DE1695414B2 (enExample) |
| ES (3) | ES340454A1 (enExample) |
| FR (1) | FR1531495A (enExample) |
| GB (1) | GB1168801A (enExample) |
| GR (1) | GR33689B (enExample) |
| IL (1) | IL27968A (enExample) |
| IT (1) | IT1056713B (enExample) |
| LU (1) | LU53658A1 (enExample) |
| NL (1) | NL149490B (enExample) |
| OA (1) | OA02592A (enExample) |
| SE (1) | SE320664B (enExample) |
| SU (1) | SU470113A3 (enExample) |
| YU (1) | YU33191B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003074488A1 (en) * | 2002-03-07 | 2003-09-12 | Obschestvo S Ogranichennoi Otvetstvennoctju, Polivit | Method for producing ethyl ether of 6-fluorine-7-chlorine-1.4-dihydro-4-oxo-3-quinolinecarboxilic acid |
| US9120749B2 (en) | 2010-07-30 | 2015-09-01 | Oncotherapy Science, Inc. | Quinoline derivatives and MELK inhibitors containing the same |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL31508A (en) * | 1968-02-19 | 1972-02-29 | Merck & Co Inc | Antipyretic preparations containing a history of esters of the 4-hydroxy-3-quinoline carboxylic acid esters |
| US11246836B2 (en) | 2018-05-17 | 2022-02-15 | Bluelight Pharmatech Co., Ltd. | Intramuscular depot of decoquinate compositions and method of prophylaxis and treatment thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3172811A (en) * | 1965-03-09 | Quinolone proteus infection treatment | ||
| BE587330A (enExample) * | 1959-04-13 | 1900-01-01 | ||
| FR1505313A (fr) * | 1962-04-09 | 1967-12-15 | Norwich Pharma Co | Esters d'alkyle inférieur des acides 6, 7-dialkoxy (inférieur)-4-hydroxy-3-quinoléine carboxyliques et leur procédé de préparation |
| GB1076828A (en) * | 1963-12-12 | 1967-07-26 | Warner Lambert Pharmaceutical | Methylenedioxy quinoline derivatives |
| US3414576A (en) * | 1965-02-19 | 1968-12-03 | Ici Ltd | 7-n-dodecyloxy and 7-benzyloxy-4-hydroxy-3-carbalkoxy quinolines |
| US3397208A (en) * | 1965-02-24 | 1968-08-13 | Norwich Pharma Co | Method for preparing 4-hydroxy-6, 7-dialkoxy-3-carboalkoxyquinolines and novel 4-chloro-6, 7-dialkoxy-3-carboalkoxyquinolines useful therein |
-
1966
- 1966-08-04 GB GB35037/66A patent/GB1168801A/en not_active Expired
-
1967
- 1967-05-03 OA OA52932A patent/OA02592A/xx unknown
- 1967-05-09 SE SE6500/67A patent/SE320664B/xx unknown
- 1967-05-10 BE BE698305D patent/BE698305A/xx not_active IP Right Cessation
- 1967-05-10 CH CH661567A patent/CH477443A/fr not_active IP Right Cessation
- 1967-05-10 CH CH65569A patent/CH490385A/fr not_active IP Right Cessation
- 1967-05-11 IL IL27968A patent/IL27968A/en unknown
- 1967-05-11 CS CS3413A patent/CS170120B2/cs unknown
- 1967-05-12 AT AT680768A patent/AT278803B/de not_active IP Right Cessation
- 1967-05-12 DE DE1967M0073970 patent/DE1695414B2/de active Granted
- 1967-05-12 GR GR670133689A patent/GR33689B/el unknown
- 1967-05-12 LU LU53658D patent/LU53658A1/xx unknown
- 1967-05-12 AT AT451467A patent/AT272346B/de active
- 1967-05-12 FR FR106298A patent/FR1531495A/fr not_active Expired
- 1967-05-12 ES ES340454A patent/ES340454A1/es not_active Expired
- 1967-05-12 AT AT680868A patent/AT283043B/de not_active IP Right Cessation
- 1967-05-12 NL NL676706700A patent/NL149490B/xx not_active IP Right Cessation
- 1967-05-13 YU YU0961/67A patent/YU33191B/xx unknown
- 1967-05-13 SU SU1157352A patent/SU470113A3/ru active
- 1967-05-13 IT IT16071/67A patent/IT1056713B/it active
- 1967-11-06 US US680965A patent/US3544686A/en not_active Expired - Lifetime
-
1968
- 1968-02-29 ES ES351083A patent/ES351083A1/es not_active Expired
-
1969
- 1969-01-28 ES ES363013A patent/ES363013A2/es not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003074488A1 (en) * | 2002-03-07 | 2003-09-12 | Obschestvo S Ogranichennoi Otvetstvennoctju, Polivit | Method for producing ethyl ether of 6-fluorine-7-chlorine-1.4-dihydro-4-oxo-3-quinolinecarboxilic acid |
| US9120749B2 (en) | 2010-07-30 | 2015-09-01 | Oncotherapy Science, Inc. | Quinoline derivatives and MELK inhibitors containing the same |
| RU2582610C2 (ru) * | 2010-07-30 | 2016-04-27 | Онкотерапи Сайенс, Инк. | Производные хинолина и содержащие их ингибиторы melk |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6706700A (enExample) | 1967-11-14 |
| DE1695414A1 (de) | 1971-04-15 |
| GR33689B (el) | 1968-01-10 |
| AT283043B (de) | 1970-07-27 |
| BE698305A (enExample) | 1967-11-10 |
| GB1168801A (en) | 1969-10-29 |
| ES340454A1 (es) | 1968-08-01 |
| IL27968A (en) | 1971-11-29 |
| YU33191B (en) | 1976-06-30 |
| CH477443A (fr) | 1969-08-31 |
| AT278803B (de) | 1970-02-10 |
| FR1531495A (fr) | 1968-07-05 |
| CS170120B2 (enExample) | 1976-08-27 |
| LU53658A1 (enExample) | 1967-07-12 |
| SE320664B (enExample) | 1970-02-16 |
| AT272346B (de) | 1969-07-10 |
| DE1695414B2 (de) | 1976-10-21 |
| YU96167A (en) | 1975-12-31 |
| IT1056713B (it) | 1982-02-20 |
| CH490385A (fr) | 1970-05-15 |
| ES351083A1 (es) | 1969-10-16 |
| NL149490B (nl) | 1976-05-17 |
| OA02592A (fr) | 1970-05-05 |
| US3544686A (en) | 1970-12-01 |
| ES363013A2 (es) | 1970-12-01 |
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