IE37526B1 - Improved process for making 2-quinoxaline-carboxamide-1,4-dioxides - Google Patents
Improved process for making 2-quinoxaline-carboxamide-1,4-dioxidesInfo
- Publication number
- IE37526B1 IE37526B1 IE580/73A IE58073A IE37526B1 IE 37526 B1 IE37526 B1 IE 37526B1 IE 580/73 A IE580/73 A IE 580/73A IE 58073 A IE58073 A IE 58073A IE 37526 B1 IE37526 B1 IE 37526B1
- Authority
- IE
- Ireland
- Prior art keywords
- alkyl
- alkoxy
- hydrogen
- carbonyl
- methoxy
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/12—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
- Paints Or Removers (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1432443 2 - Quinoxaline - carboxamide - 1,4- dioxides PFIZER Inc 26 March 1973 [1 May 1972] 14518/73 Heading C2C Compounds I: in which one of X 1 and X 2 is hydrogen, chloro, fluoro, bromo, methyl, methoxy, trifluoromethyl or -SO 2 -NR 3 R 4 (where R 3 and R 4 are hydrogen or methyl) and the other is hydrogen, chloro, bromo, methyl or methoxy with the proviso that when one of X 1 and X 2 is SO 2 -NR 3 R 4 , the other is hydrogen, R 1 is hydrogen, alkyl, cycloalkyl, hydroxyalkyl, phenyl or allyl, R 2 is hydrogen, allyl cycloalkyl, benzyl, alkyl (optionally substituted by amino, mono- or di-(C 1-4 alkyl)amino, pyrrolo, piperazino, pyrrolidino, piperidino, morpholino, piperazino (optionally N-substituted by hydroxy-C 1-4 alkyl, C 1-4 alkanoyl, C 1-4 alkyl or (C 1-4 alkoxy) carbonyl), imidazoldino, hydroxy, C 1-4 alkoxy, carboxy, (C 1-4 alkoxy) carbonyl, carbamoyl, mono- or di-(C 1-4 alkyl) carbamyl, C 1-4 alkanoyloxy or C 1-4 alkanoylamino) or phenyl (optionally substituted by C 1-4 alkyl, C 1-4 alkoxy, amino, mono- or di-(C 1-4 alkyl) amino, carboxy, (C 1-4 alkoxy) carbonyl, hydroxy, carbamoyl; or trifluoromethyl) or NR 1 R 2 represents pyrrolo, pyrrolidino, piperidino, morpholino, piperazino (optionally, N-substituted by C 1-4 alkyl, hydroxy C 1-4 alkyl, C 1-4 alkanoyl or (C 1-4 alkoxy) carbonyl) are prepared by reacting a benzofuroxan II: with an amine HNR 1 R 2 and a pyruvic acid ester CH 3 -CO-CO-OR in which R is an ester forming group preferably C 1-6 alkyl, phenyl (optionally substituted by methyl, methoxy or chloro), benzyl (optionally substituted by methoxy or bromo), phenethyl, chloroethyl, hydroxyethyl, dimethylaminopropyl, methoxyethyl or cyclohexyl. Compound II (X 1 =CF 3 , X 2 =H) is prepared from 2 - nitro - 4 - trifluoromethylaniline with NaNO 2 and cone. H 2 SO 4 to form an azide which cyclizes on reflux. Compounds II (X 1 = SO 2 NR 3 R 4 , X 2 =H; X 1 =OMe, X 2 =Me; X 1 = Cl, X 2 =Me or MeO) are prepared by reacting an X 1 , X 2 substituted 2-nitroaniline with NaOCl solution.
[GB1432443A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24937372A | 1972-05-01 | 1972-05-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE37526L IE37526L (en) | 1973-11-01 |
| IE37526B1 true IE37526B1 (en) | 1977-08-17 |
Family
ID=22943199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE580/73A IE37526B1 (en) | 1972-05-01 | 1973-04-12 | Improved process for making 2-quinoxaline-carboxamide-1,4-dioxides |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS5726275B2 (en) |
| AT (1) | AT333767B (en) |
| BE (1) | BE797983A (en) |
| CA (1) | CA1002047A (en) |
| CH (2) | CH568988A5 (en) |
| DE (1) | DE2316765A1 (en) |
| DK (1) | DK143336C (en) |
| ES (1) | ES413579A1 (en) |
| FI (1) | FI55505C (en) |
| FR (1) | FR2182957B1 (en) |
| GB (1) | GB1432443A (en) |
| IE (1) | IE37526B1 (en) |
| IN (1) | IN139311B (en) |
| NL (1) | NL7305048A (en) |
| NO (1) | NO139173C (en) |
| PH (1) | PH12684A (en) |
| PL (1) | PL96591B1 (en) |
| SE (1) | SE405853B (en) |
| ZA (1) | ZA732418B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5128121A (en) * | 1974-09-04 | 1976-03-09 | Nagashima Special Paint | SUBERIDOMETORYOOYOBISONOSEIZOHOHO |
| FR2350096A1 (en) | 1976-05-03 | 1977-12-02 | Oreal | COMPOSITIONS INTENDED FOR COLORING THE SKIN BASED ON QUINOXALINE DERIVATIVES |
| DE2747700A1 (en) * | 1977-10-25 | 1979-05-03 | Bayer Ag | PROCESS FOR PRODUCING NEW QUINOXALIN-DI-N-OXIDES AND THEIR USE AS A MEDICINAL PRODUCT |
| WO1995009159A1 (en) * | 1993-09-28 | 1995-04-06 | Otsuka Pharmaceutical Company, Limited | Quinoxaline derivative as antidiabetic agent |
| JPH09227740A (en) * | 1996-02-21 | 1997-09-02 | Daicel Chem Ind Ltd | Glass fiber-reinforced polystyrene-based resin composition |
-
1973
- 1973-03-22 SE SE7304084A patent/SE405853B/en unknown
- 1973-03-26 GB GB1451873A patent/GB1432443A/en not_active Expired
- 1973-03-28 CA CA167,369A patent/CA1002047A/en not_active Expired
- 1973-04-02 PH PH14482A patent/PH12684A/en unknown
- 1973-04-04 DE DE2316765A patent/DE2316765A1/en not_active Withdrawn
- 1973-04-05 FI FI1052/73A patent/FI55505C/en active
- 1973-04-09 IN IN829/CAL/73A patent/IN139311B/en unknown
- 1973-04-09 ZA ZA732418A patent/ZA732418B/en unknown
- 1973-04-10 BE BE1004953A patent/BE797983A/en unknown
- 1973-04-11 FR FR7313108A patent/FR2182957B1/fr not_active Expired
- 1973-04-11 ES ES413579A patent/ES413579A1/en not_active Expired
- 1973-04-11 DK DK196673A patent/DK143336C/en active
- 1973-04-11 AT AT321073A patent/AT333767B/en not_active IP Right Cessation
- 1973-04-11 NL NL7305048A patent/NL7305048A/xx not_active Application Discontinuation
- 1973-04-12 CH CH526373A patent/CH568988A5/xx not_active IP Right Cessation
- 1973-04-12 IE IE580/73A patent/IE37526B1/en unknown
- 1973-04-12 NO NO1525/73A patent/NO139173C/en unknown
- 1973-04-12 CH CH707475A patent/CH568307A5/xx not_active IP Right Cessation
- 1973-04-12 PL PL1973161873A patent/PL96591B1/en unknown
- 1973-04-12 JP JP4091773A patent/JPS5726275B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2316765A1 (en) | 1973-11-15 |
| CA1002047A (en) | 1976-12-21 |
| FR2182957A1 (en) | 1973-12-14 |
| PH12684A (en) | 1979-07-18 |
| BE797983A (en) | 1973-10-10 |
| AT333767B (en) | 1976-12-10 |
| JPS5726275B2 (en) | 1982-06-03 |
| PL96591B1 (en) | 1978-01-31 |
| ES413579A1 (en) | 1976-01-16 |
| DK143336C (en) | 1981-12-07 |
| FR2182957B1 (en) | 1976-09-10 |
| NL7305048A (en) | 1973-11-05 |
| ATA321073A (en) | 1976-04-15 |
| FI55505C (en) | 1979-08-10 |
| ZA732418B (en) | 1974-02-27 |
| IN139311B (en) | 1976-06-05 |
| NO139173B (en) | 1978-10-09 |
| DK143336B (en) | 1981-08-10 |
| CH568307A5 (en) | 1975-10-31 |
| IE37526L (en) | 1973-11-01 |
| GB1432443A (en) | 1976-04-14 |
| JPS4924980A (en) | 1974-03-05 |
| NO139173C (en) | 1979-01-17 |
| FI55505B (en) | 1979-04-30 |
| SE405853B (en) | 1979-01-08 |
| CH568988A5 (en) | 1975-11-14 |
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