GB824468A - Phenazine derivatives and their preparation - Google Patents
Phenazine derivatives and their preparationInfo
- Publication number
- GB824468A GB824468A GB30948/57A GB3094857A GB824468A GB 824468 A GB824468 A GB 824468A GB 30948/57 A GB30948/57 A GB 30948/57A GB 3094857 A GB3094857 A GB 3094857A GB 824468 A GB824468 A GB 824468A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- salt
- general formula
- phenylenediamine
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- -1 phenyl radicals Chemical class 0.000 abstract 5
- 150000003839 salts Chemical class 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 230000001590 oxidative effect Effects 0.000 abstract 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 abstract 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 abstract 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
- 150000004982 aromatic amines Chemical class 0.000 abstract 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- HCBPHBQMSDVIPZ-UHFFFAOYSA-N methylcyclohexatriene Chemical class CC1=CC=C=C[CH]1 HCBPHBQMSDVIPZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000000814 tuberculostatic agent Substances 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
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/46—Phenazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises phenazine derivatives of the general formula <FORM:0824468/IV (b)/1> (wherein Ar and Ar1 represent phenyl radicals which may be substituted, identically or differently, by halogen atoms or alkyl or alkoxy groups of 1-6 carbon atoms, and R represents a phenyl radical, which may be substituted as defined for Ar and Ar1, or an alkyl, cycloalkyl or dialkylaminoalkyl radical, but may not represent an unsubstituted phenyl radical if each of Ar and Ar1 represents an unsubstituted phenyl or unsubstituted p-tolyl radical, and wherein at least two of Ar, Ar1 and R are identical), and the preparation thereof by the following processes: (a) reacting a condensation product of pyrocatechol and an arylamine Ar-NH2, having one of the tautomeric formul <FORM:0824468/IV (b)/2> or <FORM:0824468/IV (b)/3> with a salt of an N-substituted o-phenylenediamine of the general formula <FORM:0824468/IV (b)/4> (b) (when R is an aromatic radical identical with Ar or Ar1) heating a salt of a compound of the general formula <FORM:0824468/IV (b)/5> or <FORM:0824468/IV (b)/6> with an amine NH2-Ar1 or NH2-Ar; (c) when R is an alkyl, cycloalkyl or dialkylaminoalkyl radical and Ar is identical with Ar1) heating a salt of a compound of the general formula <FORM:0824468/IV (b)/7> with at least two molecular proportions of an arylamine NH2-Ar. The products are useful as tuberculostatic agents. Starting materials for process (b) are prepared by oxidizing an N-Ar-o-phenylenediamine (in which Ar is not unsubstituted phenyl) with ferric chloride, or oxidizing a salt of an N-Ar1-o-phenylenediamine with benzoquinone, and those for process (c) by oxidizing solutions of mineral acid salts of N-R-o-phenylenediamines with ferric chloride or benzoquinone.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH824468X | 1956-10-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB824468A true GB824468A (en) | 1959-12-02 |
Family
ID=4539779
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB30948/57A Expired GB824468A (en) | 1956-10-04 | 1957-10-03 | Phenazine derivatives and their preparation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB824468A (en) |
-
1957
- 1957-10-03 GB GB30948/57A patent/GB824468A/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1087831A (en) | Benztriazines | |
| GB1474682A (en) | Formanidines | |
| GB1449588A (en) | Process for the preparation of 1,2,4-triazole derivatives | |
| IL68228A (en) | Thiomethylpyridine derivatives,process for the production thereof and medicaments containing them | |
| GB824468A (en) | Phenazine derivatives and their preparation | |
| GB1252479A (en) | ||
| GB1445595A (en) | 4-aminoquinoline derivatives and intermediates for their pre paration | |
| GB1038735A (en) | New condensed heterocyclic compounds, their production and compositions containing them | |
| GB907646A (en) | Method of production of new derivatives of diazepin | |
| GB987599A (en) | ||
| US2561948A (en) | Aminoalkylated diamino diphenyl sulfones | |
| GB599714A (en) | Manufacture of biguanide derivatives | |
| GB894428A (en) | Process for the manufacture of basically substituted phthalazines | |
| GB611476A (en) | Improvements in and relating to the production of secondary diamines | |
| ES387448A1 (en) | Fibre-reacrive copper-complex monoazo dyestuffs | |
| GB1254928A (en) | beta-ALKOXYACRYLIC ACID AMIDES | |
| ES237916A1 (en) | Procedure for the preparation of new derivatives of the fenacine (Machine-translation by Google Translate, not legally binding) | |
| GB827446A (en) | Improvements in the production of aromatic aminosulphonyl-amidines | |
| GB877106A (en) | Substituted urea complex salts | |
| GB543846A (en) | Manufacture of indole derivatives | |
| GB1268612A (en) | New n-alkoxyalkylene-alkyl ureas and compositions containing them | |
| GB864021A (en) | Manufacture of phosphorus-containing ethylene imine type compounds | |
| GB767749A (en) | New triazine derivatives | |
| GB690465A (en) | Improvements in or relating to thiaxanthone derivatives | |
| GB859445A (en) | Basically substituted alkyl xanthine derivatives and acid addition salts thereof and a process for their production |