SU500756A3 - Способ получени производных 5-нитрохинолина - Google Patents
Способ получени производных 5-нитрохинолинаInfo
- Publication number
- SU500756A3 SU500756A3 SU1959055A SU1959055A SU500756A3 SU 500756 A3 SU500756 A3 SU 500756A3 SU 1959055 A SU1959055 A SU 1959055A SU 1959055 A SU1959055 A SU 1959055A SU 500756 A3 SU500756 A3 SU 500756A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- nitro
- quinoline
- found
- calculated
- atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- NDDZXHOCOKCNBM-UHFFFAOYSA-N 5-nitroquinoline Chemical class C1=CC=C2C([N+](=O)[O-])=CC=CC2=N1 NDDZXHOCOKCNBM-UHFFFAOYSA-N 0.000 title 1
- -1 (2-thienyl) - Chemical class 0.000 claims 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 8
- 125000004429 atom Chemical group 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 239000012265 solid product Substances 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- RJIWZDNTCBHXAL-UHFFFAOYSA-N nitroxoline Chemical compound C1=CN=C2C(O)=CC=C([N+]([O-])=O)C2=C1 RJIWZDNTCBHXAL-UHFFFAOYSA-N 0.000 claims 4
- 239000012044 organic layer Substances 0.000 claims 4
- 239000000047 product Substances 0.000 claims 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 238000009833 condensation Methods 0.000 claims 3
- 230000005494 condensation Effects 0.000 claims 3
- 238000002844 melting Methods 0.000 claims 3
- 230000008018 melting Effects 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 239000007787 solid Substances 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 239000005457 ice water Substances 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- 239000000155 melt Substances 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 239000000725 suspension Substances 0.000 claims 2
- WOSOHFBLZPFTTC-UHFFFAOYSA-N (5-nitroquinolin-8-yl) N,N-dibutylcarbamate Chemical compound [N+](=O)([O-])C1=C2C=CC=NC2=C(C=C1)OC(N(CCCC)CCCC)=O WOSOHFBLZPFTTC-UHFFFAOYSA-N 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 claims 1
- FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 claims 1
- 241000191291 Abies alba Species 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
- 235000001258 Cinchona calisaya Nutrition 0.000 claims 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 1
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 claims 1
- 241000746935 Nolina Species 0.000 claims 1
- 241000577218 Phenes Species 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 1
- 229910052770 Uranium Inorganic materials 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 229920000180 alkyd Polymers 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 208000006278 hypochromic anemia Diseases 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229960003540 oxyquinoline Drugs 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- 239000011148 porous material Substances 0.000 claims 1
- 238000001556 precipitation Methods 0.000 claims 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 claims 1
- 229960000948 quinine Drugs 0.000 claims 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 claims 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
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
- C07D215/32—Esters
- C07D215/34—Carbamates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7230894A FR2197512B1 (enExample) | 1972-08-31 | 1972-08-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU500756A3 true SU500756A3 (ru) | 1976-01-25 |
Family
ID=9103729
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1959055A SU500756A3 (ru) | 1972-08-31 | 1973-08-30 | Способ получени производных 5-нитрохинолина |
| SU2066959A SU503519A3 (ru) | 1972-08-31 | 1974-10-14 | Способ получени производных 5-нитрохинолина |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU2066959A SU503519A3 (ru) | 1972-08-31 | 1974-10-14 | Способ получени производных 5-нитрохинолина |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS4966683A (enExample) |
| BE (1) | BE804218A (enExample) |
| CA (1) | CA1010871A (enExample) |
| CH (1) | CH585718A5 (enExample) |
| DD (1) | DD107573A5 (enExample) |
| DE (1) | DE2344010A1 (enExample) |
| ES (1) | ES418331A1 (enExample) |
| FR (1) | FR2197512B1 (enExample) |
| GB (1) | GB1382571A (enExample) |
| HU (1) | HU167953B (enExample) |
| IL (1) | IL42969A (enExample) |
| IT (1) | IT990427B (enExample) |
| NL (1) | NL7311921A (enExample) |
| SU (2) | SU500756A3 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2154636C1 (ru) * | 1999-07-30 | 2000-08-20 | Субоч Георгий Анатольевич | Способ получения 5-нитро-8-оксихинолина |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0387510A1 (de) * | 1989-02-10 | 1990-09-19 | Bayer Ag | Substituierte 8-Carbamoyloxychinolin-Derivate, Verfahren zu deren Herstellung, sowie deren Verwendung zur Bekämpfung von Schädlingen |
| US12152048B2 (en) * | 2018-09-29 | 2024-11-26 | Jiangsu Yahong Meditech Co., Ltd. | Nitroxoline prodrug and use thereof |
| TWI874355B (zh) * | 2020-02-14 | 2025-03-01 | 中國大陸商江蘇亞虹醫藥科技股份有限公司 | 硝羥喹啉前藥及其用途 |
| CN111514142B (zh) * | 2020-05-29 | 2021-04-06 | 江苏亚虹医药科技股份有限公司 | 含硝羟喹啉前药的药物组合物及其制备方法和应用 |
-
1972
- 1972-08-31 FR FR7230894A patent/FR2197512B1/fr not_active Expired
-
1973
- 1973-08-13 IL IL42969A patent/IL42969A/en unknown
- 1973-08-28 CA CA179,800A patent/CA1010871A/fr not_active Expired
- 1973-08-30 BE BE135109A patent/BE804218A/xx unknown
- 1973-08-30 ES ES418331A patent/ES418331A1/es not_active Expired
- 1973-08-30 CH CH1245173A patent/CH585718A5/xx not_active IP Right Cessation
- 1973-08-30 SU SU1959055A patent/SU500756A3/ru active
- 1973-08-30 JP JP48096772A patent/JPS4966683A/ja active Pending
- 1973-08-30 NL NL7311921A patent/NL7311921A/xx not_active Application Discontinuation
- 1973-08-30 GB GB4081473A patent/GB1382571A/en not_active Expired
- 1973-08-30 HU HURO744A patent/HU167953B/hu unknown
- 1973-08-30 IT IT52248/73A patent/IT990427B/it active
- 1973-08-31 DE DE19732344010 patent/DE2344010A1/de active Pending
- 1973-08-31 DD DD173206A patent/DD107573A5/xx unknown
-
1974
- 1974-10-14 SU SU2066959A patent/SU503519A3/ru active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2154636C1 (ru) * | 1999-07-30 | 2000-08-20 | Субоч Георгий Анатольевич | Способ получения 5-нитро-8-оксихинолина |
Also Published As
| Publication number | Publication date |
|---|---|
| DD107573A5 (enExample) | 1974-08-12 |
| IT990427B (it) | 1975-06-20 |
| NL7311921A (enExample) | 1974-03-04 |
| JPS4966683A (enExample) | 1974-06-27 |
| FR2197512A1 (enExample) | 1974-03-29 |
| IL42969A0 (en) | 1973-11-28 |
| BE804218A (fr) | 1974-02-28 |
| CA1010871A (fr) | 1977-05-24 |
| CH585718A5 (enExample) | 1977-03-15 |
| IL42969A (en) | 1977-01-31 |
| ES418331A1 (es) | 1976-03-16 |
| FR2197512B1 (enExample) | 1977-01-14 |
| SU503519A3 (ru) | 1976-02-15 |
| DE2344010A1 (de) | 1974-03-07 |
| HU167953B (enExample) | 1976-01-28 |
| GB1382571A (en) | 1975-02-05 |
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