IE37526L - Quinoxaline-1, 4-dioxides - Google Patents
Quinoxaline-1, 4-dioxidesInfo
- Publication number
- IE37526L IE37526L IE730580A IE58073A IE37526L IE 37526 L IE37526 L IE 37526L IE 730580 A IE730580 A IE 730580A IE 58073 A IE58073 A IE 58073A IE 37526 L IE37526 L IE 37526L
- Authority
- IE
- Ireland
- Prior art keywords
- alkyl
- alkoxy
- hydrogen
- carbonyl
- methoxy
- Prior art date
Links
- CKIHZSGJPSDCNC-UHFFFAOYSA-N Quindoxin Chemical class C1=CC=C2N([O-])C=C[N+](=O)C2=C1 CKIHZSGJPSDCNC-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 11
- -1 chloro, fluoro, bromo, methyl Chemical group 0.000 abstract 10
- 125000003545 alkoxy group Chemical group 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 150000002431 hydrogen Chemical class 0.000 abstract 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- GLLHZHAFSZJULJ-UHFFFAOYSA-N 1-oxido-4-oxoquinoxalin-4-ium-2-carboxamide Chemical class C1=CC=CC2=[N+]([O-])C(C(=O)N)=C[N+]([O-])=C21 GLLHZHAFSZJULJ-UHFFFAOYSA-N 0.000 abstract 1
- ATXBGHLILIABGX-UHFFFAOYSA-N 2-nitro-4-(trifluoromethyl)aniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O ATXBGHLILIABGX-UHFFFAOYSA-N 0.000 abstract 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical class NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- OKEAMBAZBICIFP-UHFFFAOYSA-N 3-oxido-2,1,3-benzoxadiazol-3-ium Chemical compound C1=CC=CC2=[N+]([O-])ON=C21 OKEAMBAZBICIFP-UHFFFAOYSA-N 0.000 abstract 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 abstract 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910019093 NaOCl Inorganic materials 0.000 abstract 1
- LCTONWCANYUPML-UHFFFAOYSA-N PYRUVIC-ACID Natural products CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 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 abstract 1
- 150000002148 esters Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 229940107700 pyruvic acid Drugs 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 abstract 1
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)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (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 true IE37526L (en) | 1973-11-01 |
| IE37526B1 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 |
| AU674613B2 (en) * | 1993-09-28 | 1997-01-02 | Otsuka Pharmaceutical Co., Ltd. | Quinoxaline derivative as antidiabetic agent |
| JPH09227740A (en) * | 1996-02-21 | 1997-09-02 | Daicel Chem Ind Ltd | Glass fiber reinforced polystyrene 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 ES ES413579A patent/ES413579A1/en not_active Expired
- 1973-04-11 NL NL7305048A patent/NL7305048A/xx not_active Application Discontinuation
- 1973-04-11 AT AT321073A patent/AT333767B/en not_active IP Right Cessation
- 1973-04-11 FR FR7313108A patent/FR2182957B1/fr not_active Expired
- 1973-04-11 DK DK196673A patent/DK143336C/en active
- 1973-04-12 CH CH526373A patent/CH568988A5/xx not_active IP Right Cessation
- 1973-04-12 NO NO1525/73A patent/NO139173C/en unknown
- 1973-04-12 IE IE580/73A patent/IE37526B1/en unknown
- 1973-04-12 PL PL1973161873A patent/PL96591B1/en unknown
- 1973-04-12 CH CH707475A patent/CH568307A5/xx not_active IP Right Cessation
- 1973-04-12 JP JP4091773A patent/JPS5726275B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IN139311B (en) | 1976-06-05 |
| FR2182957A1 (en) | 1973-12-14 |
| NO139173B (en) | 1978-10-09 |
| DK143336C (en) | 1981-12-07 |
| NO139173C (en) | 1979-01-17 |
| NL7305048A (en) | 1973-11-05 |
| CH568988A5 (en) | 1975-11-14 |
| CA1002047A (en) | 1976-12-21 |
| FI55505B (en) | 1979-04-30 |
| ES413579A1 (en) | 1976-01-16 |
| FI55505C (en) | 1979-08-10 |
| JPS5726275B2 (en) | 1982-06-03 |
| DE2316765A1 (en) | 1973-11-15 |
| ZA732418B (en) | 1974-02-27 |
| PL96591B1 (en) | 1978-01-31 |
| CH568307A5 (en) | 1975-10-31 |
| AT333767B (en) | 1976-12-10 |
| BE797983A (en) | 1973-10-10 |
| FR2182957B1 (en) | 1976-09-10 |
| ATA321073A (en) | 1976-04-15 |
| PH12684A (en) | 1979-07-18 |
| GB1432443A (en) | 1976-04-14 |
| SE405853B (en) | 1979-01-08 |
| JPS4924980A (en) | 1974-03-05 |
| IE37526B1 (en) | 1977-08-17 |
| DK143336B (en) | 1981-08-10 |
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