GB1160218A - Substituted 10-Aminoalkylanthracenes - Google Patents
Substituted 10-AminoalkylanthracenesInfo
- Publication number
- GB1160218A GB1160218A GB299169A GB299169A GB1160218A GB 1160218 A GB1160218 A GB 1160218A GB 299169 A GB299169 A GB 299169A GB 299169 A GB299169 A GB 299169A GB 1160218 A GB1160218 A GB 1160218A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- prepared
- alkyl
- bromo
- give
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,160,218. Anthracene derivatives. SMITH KLINE & FRENCH LABORATORIES. 8 Feb., 1967 [14 Feb., 1966], No. 2991/69. Divided out of 1,160,217. Heading C2C. Novel compounds of formula wherein R is H or C 1-4 -alkyl, Y is halogen, C 1-4 - alkyl, CF 3 , alkylthio, CN or dimethylsulphamoyl, A is C 2-4 alkylene and Z is amino or mono- or di-C 1-4 -alkylamino or a monocyclic heterocyclic amino group containing 4-12 carbon atoms, such as morpholino, thiomorpholino, pyrrolidino, piperidino, or piperazino, or piperazino substituted in the 4-position by C 1-4 alkyl, hydroxy-C 1-4 -alkyl, #-acetoxy-C 1-4 -alkyl, or #-hydroxy-alkoxy-C 1-4 -alkyl, and acid addition salts thereof are prepared by reaction of a compound of Formula II or a 9-alkyl derivative thereof with the compound HZ optionally followed by salt formation and/or modification of any 4-piperazine substituent. Compounds of Formula II above are prepared by action of HBr on compounds of Formula III which are themselves prepared by action of CH 3 OAMg Halogen on a compound of Formula IV Compounds of Formula IV are prepared, for example, as follows for 2-trifluoromethyl-10- anthrone which is prepared by reaction of phenyl magnesium bromide with 2-bromo-4- trifluoromethylbenzonitrile to give 2-bromo-4- trifluoromethyl-diphenyl-methane which is reduced to yield 2-bromo-4-trifluoromethyl-diphenylmethane which is reacted first with Mg then with CO 2 to give 2-benzyl-5-trifluoromethylbenzoic acid which is cyclized to give the required anthrone. 9-Alkyl substituted compounds of Formula II above are prepared, for example, by action of HBr on a compound of Formula V which is prepared by action of CH 3 O-A-Mg-halogen on a nitrile of Formula VI Nitriles of Formula VI above are prepared. for example, as follows for 2-(α-methylbenzyl)-5- trifluoromethylbenzonitrile which is prepared by reaction of trimethylsulfoxonium iodide and a strong alkali with 2-bromo-4-trifluoromethylbenzophenone to give 1-phenyl-1-(2-bromo-4- trifluoromethylphenyl)-ethylene oxide which is reduced with a bimetal hydride to give α- phenyl - α - (2 - bromo - 4 - trifluoromethylphenyl)-ethanol which on action of P/Hl gives 2 - (α - methylbenzyl) - 5 - trifluoromethyl - bromobenzene which with cuprous cyanide gives the required nitrile.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US52697566A | 1966-02-14 | 1966-02-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1160218A true GB1160218A (en) | 1969-08-06 |
Family
ID=24099585
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB611667A Expired GB1160217A (en) | 1966-02-14 | 1967-02-08 | Substituted 10-Aminoalkyl-9,10-Dihydroanthracenes |
GB299169A Expired GB1160218A (en) | 1966-02-14 | 1967-02-08 | Substituted 10-Aminoalkylanthracenes |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB611667A Expired GB1160217A (en) | 1966-02-14 | 1967-02-08 | Substituted 10-Aminoalkyl-9,10-Dihydroanthracenes |
Country Status (11)
Country | Link |
---|---|
BE (1) | BE694036A (en) |
CH (1) | CH499486A (en) |
DE (1) | DE1618850C3 (en) |
DK (1) | DK134514B (en) |
ES (1) | ES336734A1 (en) |
FR (1) | FR6180M (en) |
GB (2) | GB1160217A (en) |
IL (1) | IL27389A (en) |
IT (1) | IT1033005B (en) |
NL (1) | NL153853B (en) |
SE (1) | SE309037B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3694514A (en) * | 1971-03-05 | 1972-09-26 | Smith Kline French Lab | 10-bromoalkyl-anthracenes |
-
1967
- 1967-02-03 CH CH160667A patent/CH499486A/en not_active IP Right Cessation
- 1967-02-05 IL IL2738967A patent/IL27389A/en unknown
- 1967-02-08 GB GB611667A patent/GB1160217A/en not_active Expired
- 1967-02-08 GB GB299169A patent/GB1160218A/en not_active Expired
- 1967-02-08 DE DE1967S0108223 patent/DE1618850C3/en not_active Expired
- 1967-02-09 IT IT1247067A patent/IT1033005B/en active
- 1967-02-11 ES ES336734A patent/ES336734A1/en not_active Expired
- 1967-02-13 SE SE198267A patent/SE309037B/xx unknown
- 1967-02-14 NL NL6702224A patent/NL153853B/en not_active IP Right Cessation
- 1967-02-14 FR FR94795A patent/FR6180M/fr not_active Expired
- 1967-02-14 BE BE694036D patent/BE694036A/en not_active IP Right Cessation
- 1967-02-14 DK DK81167A patent/DK134514B/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
DK134514B (en) | 1976-11-22 |
SE309037B (en) | 1969-03-10 |
DE1618850C3 (en) | 1980-10-30 |
DE1618850B2 (en) | 1980-02-21 |
CH499486A (en) | 1970-11-30 |
DE1618850A1 (en) | 1971-07-22 |
NL153853B (en) | 1977-07-15 |
BE694036A (en) | 1967-08-14 |
FR6180M (en) | 1968-07-15 |
GB1160217A (en) | 1969-08-06 |
IL27389A (en) | 1971-11-29 |
ES336734A1 (en) | 1968-01-01 |
NL6702224A (en) | 1967-08-15 |
IT1033005B (en) | 1979-07-10 |
DK134514C (en) | 1977-04-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ES385635A1 (en) | 2-(n-allyl-phenylamino)-imidazolines-(2)and salts thereof | |
ES445928A1 (en) | Quaternary imidazole compounds as microbicides | |
GB842804A (en) | Preparation of substituted piperazines | |
GB1111338A (en) | Aralkyl substituted resorcinols | |
GB1029920A (en) | Piperazine and piperidine compounds | |
GB1160218A (en) | Substituted 10-Aminoalkylanthracenes | |
GB1398773A (en) | Bis-basic ketones of phenoxathiins and antiviral compositions thereof | |
ES423233A1 (en) | 2-phenylamino-imidazolines-(2) | |
GB1313253A (en) | Coumarine derivatives and their use as optical brightening agents | |
ES313081A1 (en) | Phenyl-alpha-piperazino-alkanoates | |
GB1096301A (en) | 1,4-benzodioxane derivatives | |
ES419739A1 (en) | 2-aryl-amino-imidazoline-2 compounds | |
GB1316587A (en) | 4-chloropyrazolyl compounds and their use as brightening agents | |
GB1188248A (en) | 2-Isothiouronium-Methyl-Quinoxaline-1,4,di-N-Oxide-3-Carboxylic Acid Amide Halides | |
GB1210157A (en) | Novel dibenzocycloheptene amine derivatives | |
GB915259A (en) | 4-halo-3-sulfamoylbenzoic acid esters and methods for producing same | |
ES319942A1 (en) | Procedure for the obtaining of 3 ', 4', 5'-trimetoxy-3-aminoacrilofenona. (Machine-translation by Google Translate, not legally binding) | |
GB1199743A (en) | Process for the Preparation of Hydroxybenzonitriles | |
GB1108578A (en) | 5-aminomethyl-4,5,6,7-tetrahydro-4-oxoindoles | |
GB841120A (en) | Improvements in or relating to piperidine compounds | |
GB1104323A (en) | 3-phenylpyrrole derivatives and process for preparing the same | |
GB1331130A (en) | Dibenz-6,f-azocin-6-5h-ones | |
ES392388A1 (en) | Tetrahydropyridine derivatives and a process for the manufacture thereof | |
ES316528A1 (en) | Procedure for preparing agents to combat parasites. (Machine-translation by Google Translate, not legally binding) | |
GB1102162A (en) | Improvements in or relating to pyridones, phenothiazines and dibenzazepines and the manufacture thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PE | Patent expired |