SU612628A3 - Method of preparing derivatives of 1,4-quinoxaline dioxide - Google Patents
Method of preparing derivatives of 1,4-quinoxaline dioxideInfo
- Publication number
- SU612628A3 SU612628A3 SU752189810A SU2189810A SU612628A3 SU 612628 A3 SU612628 A3 SU 612628A3 SU 752189810 A SU752189810 A SU 752189810A SU 2189810 A SU2189810 A SU 2189810A SU 612628 A3 SU612628 A3 SU 612628A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- dioxide
- mol
- acid
- quinoxaline
- preparing derivatives
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/52—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
В качестве минеральной кислоты используют, например, хлористовЪдородную , серную фосфорную.As a mineral acid, for example, hydrogen chloride and sulfuric phosphoric acid are used.
Пример 1. Получение 1,4-двуокиси (2-фенилацетил)-гидразоноформилхиноксалина .Example 1. Preparation of 1,4-dioxide (2-phenylacetyl) -hydrazonoformalylquinoxaline.
75 мл водной суспензии 11,8 г (0,05 мол ) диметилацетал 1,4-двуЬкиси-2-формилхинрксалина и 4 мл концентрированной сол ной кислоты кип т т 10 мин, -а затем добавл ют 50 мл теплой воднойсуспензии 7,5 г (0,05 мол ) гидразида фенйлуксусной кислоты. Реакционную смесь постепенно охлаждают до комнатной температуры, а затем ее пере «ешивают в течение трех часов, образующийс осадок кремового цвета от ильтровывают , а затем промывают водой и этанолом . Получают 15,8 г (98%) целевого продукта с т.пл. 255-256 С.75 ml of an aqueous suspension of 11.8 g (0.05 mol) 1,4-hydroxy-2-formyl quinrxalin dimethyl acetal and 4 ml of concentrated hydrochloric acid are boiled for 10 minutes, and then 50 ml of a warm aqueous suspension of 7.5 g is added (0.05 mol) of fenylacetic acid hydrazide. The reaction mixture is gradually cooled to room temperature, and then it is diluted for three hours, the resulting cream colored precipitate is filtered off and then washed with water and ethanol. Obtain 15.8 g (98%) of the desired product with so pl. 255-256 S.
Пример 2. Получение 1 4-двуокиси 2-(l-нaфтaлaцeтил)-гидpaзoнoфopмилxинokcaлинa .Example 2. Obtaining 1 4-dioxide 2- (l-naphthalazole) -hydrazonophonylquinoxaline.
9,5 г.(0,05 мол ) 1,4-двуокиси 2-формилхиноксалина раствор ют в 100 мл воды, содержащей 0,5 мл конЦентрированной сол ной кислоты, а затем к раствору добавл ют 10,0 г (0,05 мол ) гидразида 1-нафтилуксусной кислоты. После перемешивани в течение трех часов при комнатной температурё суспензию отфильтровывают, и оссщок промывают водой и этанолом. Получают 16,2 г (87%) целевого продукта с т.пл. 246-247 С.9.5 g (0.05 mol) of 1,4-dioxide 2-formylquinoxaline is dissolved in 100 ml of water containing 0.5 ml of concentrated hydrochloric acid, and then 10.0 g (0.05 g) is added to the solution. mole) hydrazide 1-naphthylacetic acid. After stirring for three hours at room temperature, the suspension is filtered, and the juice is washed with water and ethanol. Obtain 16.2 g (87%) of the desired product with so pl. 246-247 C.
Пример 3. 1,4-двуокись 2-(п-оксибензоил)-гидразоноформилхиноксалина .Example 3. 2- (p-hydroxybenzoyl) -hydrazonoformylquinoxaline 1,4-dioxide
75 мл водной суспензии, содержащей 11,8г (0,05 мол ) диметилацетал 1 ,4-двуокиси 2-формилхиноксалина и 4 мл концентрированной сол ной кислоты , кип т т 10 мин, а затем добавл ют 25 мл теплой.водной суспензии 7,75 г (0,051 мол ) Ьидразида п-оксибензойной кислоты. Реакционную смесь Постепенно охлаждают до комнатной температуры; а затем ее перемеигавают при этой температуре в течение трех часов Выпавшие в осадок кристаллы отфильтровывают , и промывают водой и этанолом , получают 14,95 г (92.,4%) целевого продукта с т.пл. .75 ml of an aqueous suspension, containing 11.8 g (0.05 mol) of dimethyl acetal 1, 4-dioxide 2-formyl quinoxaline and 4 ml of concentrated hydrochloric acid, are boiled for 10 minutes and then 25 ml of warm suspension is added. 75 g (0.051 mol) of hydrazide p-hydroxybenzoic acid. The reaction mixture is gradually cooled to room temperature; and then it is mixed at this temperature for three hours. The precipitated crystals are filtered off and washed with water and ethanol to obtain 14.95 g (92., 4%) of the desired product with so pl. .
П р и м е.р 4. Получение 1,4-двуокиси 2-лауриноилгидразрноформилхиноксалина .EXAMPLE 4: Preparation of 1,4-dioxide 2-laurinoyl hydrazne formyl quinoxaline.
75 мл водной суспензии 11,8 г . (0,05 мол ) диметилацетал 1,4-:двуокиси 2-формилхинокс.алина и 5 мл концентрированной фосфорной кислоты кип т т 10 МИ.Н, а затем добавл ют 50 мл теплой водной суспензии 10,2 г (0,05 мол ) гидразидй лауриновой кислоты. Реакционную смесь постепенно охлаждают до комнатной температуры, а затем ее перемешивают При этой температуре в течение трех часов. Выпавшие в осадок кристаллы отфильтровывают и. промывают водой и этанолом. . 16,4 г (84,9%) целевого продукта с т.пл. .75 ml of aqueous suspension 11.8 g. (0.05 mol) dimethyl acetal 1,4-: 2-formylquinoxaline dioxide and 5 ml of concentrated phosphoric acid are boiled for 10 MN, and then 50 ml of a warm aqueous suspension of 10.2 g (0.05 mol a) hydrazide lauric acid. The reaction mixture is gradually cooled to room temperature, and then it is stirred at this temperature for three hours. The precipitated crystals are filtered and. washed with water and ethanol. . 16.4 g (84.9%) of the desired product with so pl. .
Пример 5. Получение 1,4-двуокиси .2-(п-аминобензоил)-гидразоноформилхинбксалина .Example 5. Obtaining 1,4-dioxide .2- (p-aminobenzoyl) -hydrazonoformylinhxaline.
9,5 г (О.,05 мол ) 1,4-двуокиси 2-формилхиноксалина раствор ют в 1QO м воды, содержащей 0,5 г п-толуолсульфркислоты , а затем,к раствору добавл ют раствор 7,55 г (0,05 мол ) гидразида п-аминобензойнрйкислоты а 50 мл метанола. Реакционную смесь перемешивают при комнатной температуре р течение трех часов, а затем ее отфильтровывают . Осадок промь)вают водой и этанолом. Получают 13,1 г (81,2%} целевого продукта с т.пл. .9.5 g (O., 05 mol) of 1,4-dioxide 2-formylquinoxaline is dissolved in 1QO m of water containing 0.5 g of p-toluenesulfonic acid, and then a solution of 7.55 g (0, 05 mol) of p-aminobenzoic acid hydrazide and 50 ml of methanol. The reaction mixture is stirred at room temperature for three hours and then filtered. The precipitate is washed with water and ethanol. Obtain 13.1 g (81.2%} of the desired product with so pl.
Пример 6. Получение 1,4-двуокиси 2-никотиноилгидразоноформилхиноксалина . Example 6. Obtaining 1,4-dioxide 2-nicotinoylhydrazonoformylquinoxaline.
7,55 г (0,05 мол ) этилового эфира никотиновой кислоты раствор ют в 60 мл этанола, а затем к полученному раствору по капл м добавл ют 2,6 г (0,05 мол ) гидрата гидразина. Реакционную смесь кип т т 2 час, а затем к ней по капл м добавл ют теплый раствор 9,5 г (0,05 мол ) 1,4-двуокиси 2-формилхиноксалина и 1 мл концентрированной сол ной кислоты в 140 мл метанола . -Реакционную.смесь постепенно охлаждают до комнатной температуры, а .затем ее перемешивает при этой температуре в течение двух часов. Выпавшие в осадок кристаллы отфильтровывают и промывают метанолом. В результате получают 13,2 г (85,4%) -целевого про дукта с т.пл. .7.55 g (0.05 mol) of nicotinic acid ethyl ester is dissolved in 60 ml of ethanol, and then 2.6 g (0.05 mol) of hydrazine hydrate is added dropwise to the resulting solution. The reaction mixture was boiled for 2 hours, and then a warm solution of 9.5 g (0.05 mol) of 1,4-dioxide 2-formyl-quinoxaline and 1 ml of concentrated hydrochloric acid in 140 ml of methanol was added dropwise to it. The reaction mixture is gradually cooled to room temperature, and then stirred at this temperature for two hours. The precipitated crystals are filtered and washed with methanol. The result is 13.2 g (85.4%) of the target product with so pl. .
П р и- м е р 7. Получение 1,4-двуокиси 2-изоникотиноилгидраэоноформилхиноксалина ..Example 7. Preparation of 1,4-dioxide 2-isonicotinoyl hydraone formyl quinoxaline.
При взаимодействии 11,8 г (0,05 мо . л ) диметилацетал 1,4-двуокиси 2-ij)oi милхиноксалина и 6,85 г (0,05 мол ) гидразида изоникотиновой кислоты по методике, описанной в примере 1, получают 14,4 г (93,2%) целевого продукта с т.пл. 268С. .In the interaction of 11.8 g (0.05 mo. L) dimethyl acetal 1,4-dioxide 2-ij) oi milchinoxaline and 6.85 g (0.05 mol) of isonicotinic acid hydrazide according to the method described in example 1, get 14 , 4 g (93.2%) of the desired product with so pl. 268C. .
П р и м е р 8.. Получение 1,4-дв5 окиси 2-(п-хлорбензоил)-гидразоноформилхиноксалина . .EXAMPLE 8 Preparation of 1,4-dv5 2- (p-chlorobenzoyl) -hydrazonoformylquinoxaline oxide. .
При взаимодействии 11,8 г (0,05 мол ) диметилацетал 1,4-двуокиси 2-формилхиноксалин и 8,5 г (0,05 мол ) гидразина п-хлорбензойной кислоты по методикеj описанной в примере 2, получают 16,1 г (94%) целевого продукта с пл.. .When interacting 11.8 g (0.05 mol) of dimethyl acetal 1,4-dioxide 2-formylquinoxaline and 8.5 g (0.05 mol) of p-chlorobenzoic acid hydrazine according to the procedure described in Example 2, 16.1 g are obtained ( 94%) of the target product with a pl.
; . П р и м е р - 9. Получение 1,4- вуокиси 2-(З-нитробензоил)-гидразоноформилхиноксалина . . .; . PRI me R - 9. Preparation of 1,4-2- (3-nitrobenzoyl) -hydrazonoformylquinoxaline hydroxydehydroxide. . .
Из 9,5 г (0,05 мол ) 1,4-двуокйси 2-формилхиноксалина и 9.,05 т (0,05 мо л ) гидразида З-нйтробензойной кислоты По Методике, описанной в примере 2 получают 16;15. г (91,6%) пррдукта . с т.пл.- 290°С.. . From 9.5 g (0.05 mol) of 1,4-dioxy 2-formylquinoxaline and 9., 05 t (0.05 mol liter) of hydrazide Z-nitrobenzoic acid According to the procedure described in example 2, 16 are obtained; 15. g (91.6%) of the product. with so pl. - 290 ° C..
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUEE2278A HU169299B (en) | 1974-11-21 | 1974-11-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU612628A3 true SU612628A3 (en) | 1978-06-25 |
Family
ID=10995579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752189810A SU612628A3 (en) | 1974-11-21 | 1975-11-19 | Method of preparing derivatives of 1,4-quinoxaline dioxide |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS6049634B2 (en) |
| AT (1) | AT344702B (en) |
| BE (1) | BE835763A (en) |
| CH (1) | CH623042A5 (en) |
| CS (1) | CS232703B2 (en) |
| DD (1) | DD123604A5 (en) |
| DE (1) | DE2552289C2 (en) |
| DK (1) | DK138389B (en) |
| FI (1) | FI61887C (en) |
| FR (1) | FR2291756A1 (en) |
| GB (1) | GB1479239A (en) |
| HU (1) | HU169299B (en) |
| IL (1) | IL48463A (en) |
| IN (1) | IN140110B (en) |
| NL (1) | NL7513446A (en) |
| PL (1) | PL96412B1 (en) |
| SE (2) | SE423095B (en) |
| SU (1) | SU612628A3 (en) |
| YU (1) | YU39953B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1058490B (en) * | 1976-03-18 | 1982-04-10 | Ind Chimica Prodotti Francis S | MANUFACTURING PROCEDURE OF ALCHIL 3 2 KINOXALYLMETHYLEN CARBATATE 1.4 DIOXIDE |
| HU184772B (en) * | 1980-05-23 | 1984-10-29 | Egyt Gyogyszervegyeszeti Gyar | Process for preparing quinoxaline-1,4-dioxide derivatives |
| HU184825B (en) * | 1980-09-12 | 1984-10-29 | Egyt Gyogyszervegyeszeti Gyar | Process for preparing new 2-hydroxy-methyl-quinoxaline-1,4-dioxide derivatives |
| JPS6276527A (en) * | 1985-09-30 | 1987-04-08 | Toshiba Corp | Wire bonding capillary |
| US5049561A (en) * | 1987-07-31 | 1991-09-17 | The Upjohn Company | Anthelmintic acylhydrazones, method of use and compositions |
| EP0370065A1 (en) * | 1987-07-31 | 1990-05-30 | The Upjohn Company | Anthelmintic acylhydrazones, method of use and compositions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1469485A (en) * | 1964-09-16 | 1967-02-17 | Pfizer & Co C | Process for the preparation of a new series of schiff bases |
| US3371090A (en) * | 1964-09-16 | 1968-02-27 | Pfizer & Co C | Novel antibacterial agents |
-
1974
- 1974-11-21 HU HUEE2278A patent/HU169299B/hu not_active IP Right Cessation
-
1975
- 1975-11-11 IL IL48463A patent/IL48463A/en unknown
- 1975-11-14 IN IN2177/CAL/75A patent/IN140110B/en unknown
- 1975-11-14 SE SE7512857A patent/SE423095B/en unknown
- 1975-11-17 AT AT872275A patent/AT344702B/en not_active IP Right Cessation
- 1975-11-17 CH CH1484575A patent/CH623042A5/en not_active IP Right Cessation
- 1975-11-17 FI FI753225A patent/FI61887C/en not_active IP Right Cessation
- 1975-11-18 DK DK518275AA patent/DK138389B/en unknown
- 1975-11-18 GB GB47418/75A patent/GB1479239A/en not_active Expired
- 1975-11-18 FR FR7535184A patent/FR2291756A1/en active Granted
- 1975-11-18 NL NL7513446A patent/NL7513446A/en not_active Application Discontinuation
- 1975-11-19 CS CS757830A patent/CS232703B2/en unknown
- 1975-11-19 SU SU752189810A patent/SU612628A3/en active
- 1975-11-20 PL PL1975184870A patent/PL96412B1/en unknown
- 1975-11-20 YU YU2942/75A patent/YU39953B/en unknown
- 1975-11-20 BE BE162030A patent/BE835763A/en not_active IP Right Cessation
- 1975-11-20 DD DD189588A patent/DD123604A5/xx unknown
- 1975-11-21 JP JP50139369A patent/JPS6049634B2/en not_active Expired
- 1975-11-21 DE DE2552289A patent/DE2552289C2/en not_active Expired
-
1979
- 1979-01-16 SE SE7900389A patent/SE423387B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2291756A1 (en) | 1976-06-18 |
| CH623042A5 (en) | 1981-05-15 |
| IL48463A0 (en) | 1976-01-30 |
| DD123604A5 (en) | 1977-01-05 |
| DK518275A (en) | 1976-05-22 |
| DE2552289C2 (en) | 1986-05-07 |
| CS232703B2 (en) | 1985-02-14 |
| FI61887C (en) | 1982-10-11 |
| NL7513446A (en) | 1976-05-25 |
| FI753225A (en) | 1976-05-22 |
| IN140110B (en) | 1976-09-18 |
| YU39953B (en) | 1985-06-30 |
| JPS5175082A (en) | 1976-06-29 |
| YU294275A (en) | 1982-06-30 |
| DK138389B (en) | 1978-08-28 |
| PL96412B1 (en) | 1977-12-31 |
| FI61887B (en) | 1982-06-30 |
| SE423387B (en) | 1982-05-03 |
| JPS6049634B2 (en) | 1985-11-02 |
| ATA872275A (en) | 1977-12-15 |
| IL48463A (en) | 1978-10-31 |
| HU169299B (en) | 1976-11-28 |
| GB1479239A (en) | 1977-07-06 |
| SE7512857L (en) | 1976-05-24 |
| FR2291756B1 (en) | 1978-11-10 |
| SE7900389L (en) | 1979-01-16 |
| DK138389C (en) | 1979-02-05 |
| DE2552289A1 (en) | 1976-05-26 |
| SE423095B (en) | 1982-04-13 |
| AT344702B (en) | 1977-12-15 |
| BE835763A (en) | 1976-03-16 |
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