GB793860A - Processes for the production of aziridinoquinones - Google Patents
Processes for the production of aziridinoquinonesInfo
- Publication number
- GB793860A GB793860A GB311056A GB311056A GB793860A GB 793860 A GB793860 A GB 793860A GB 311056 A GB311056 A GB 311056A GB 311056 A GB311056 A GB 311056A GB 793860 A GB793860 A GB 793860A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzoquinone
- naphthaquinone
- diphenoxy
- aziridine
- alkylthio
- 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
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
- C07D203/14—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom with carbocyclic rings directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Aziridinoquinones are prepared by reacting aziridine or a C-alkylated aziridine with a 1,4-benzoquinone or 1,4-naphthaquinone having at least one alkoxy or alkylthio radical in a position adjacent to a nuclear carbonyl radical of the quinone. The reaction is effected by stirring the reactants preferably in an inert solvent, e.g. methanol, ethanol, benzene, toluene, dioxane or petroleum ether, and at a temperature between 20 DEG and 100 DEG C. Specified aziridines include aziridine and its 2-methyl- and 2,2-dimethyl derivatives, whilst suitable quinones are monoalkoxy-, mono-alkylthio-, 2,5-dialkoxy, 2,5-dialkylthio-, 2,3,5- and 2,3,6-trialkoxy and trialkylthio-, 2,3,5,6-tetraalkoxy and tetralkylthio-1,4-benzoquinones, and mono- and polyalkoxy and alkylthio-1,4-naphthaquinones, said alkoxy and alkylthio radicals containing at most five carbon atoms. In examples: (1) and (2) tetramethoxy-1,4-benzoquinone and aziridine are refluxed in methanol, giving 3,6-dimethoxy - 2,5 - diaziridino - 1,4 - benzoquinone; (3) to (5) as in (1), tetra(ethylthio)-1,4-benzoquinone gives 3,6-di(ethylthio)-2,5-diaziridino-1,4-benzoquinone, 2,3 - dimethoxy - 1,4 - naphthaquinone yields 3-methoxy-2-aziridino-1,4-naphthaquinone, and 2,3-di(methylthio)-1,4-naphthaquinone gives 3-methylthio-2-aziridino1,4-naphthaquinone. A number of "comparative examples" illustrate the use of phenoxysubstituted quinones under similar conditions; thus 2-phenoxy-, 2,5-diphenoxy-, 2,3,5,6-tetraphenoxy-, 3,6 - dichloro - 2,5 - diphenoxy-, 3,6-dibromo - 2,5 - diphenoxy and 3,6 - diphenoxy-2,5-dimethoxy-1,4-benzoquinone, yield 2,5-diaziridino - 1,4 - benzoquinone or its 3,6 - diphenoxy-, dichloro-, or dibromoderivatives; 2,3-diphenoxy- and 2,3-di(4-methylphenoxy)-1,4-naphthaquinone yield 3-phenoxy or -(4-methylphenoxy) - 2 - aziridino - 1,4 - naphthaquinone, and 2,5-diphenoxy-1,4-benzoquinone with 2-methylaziridine gives 2,5-di(2-methylaziridino) - 1,4 - benzoquinone. Specifications 762,723 and 793,796 are referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB311056A GB793860A (en) | 1956-01-31 | 1956-01-31 | Processes for the production of aziridinoquinones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB311056A GB793860A (en) | 1956-01-31 | 1956-01-31 | Processes for the production of aziridinoquinones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB793860A true GB793860A (en) | 1958-04-23 |
Family
ID=6710393
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB311056A Expired GB793860A (en) | 1956-01-31 | 1956-01-31 | Processes for the production of aziridinoquinones |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB793860A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3025289A (en) * | 1958-07-12 | 1962-03-13 | Domagk Gerhard | 5-alkoxy-2, 3, 6-trisaziridino-1, 4-benzoquinone |
-
1956
- 1956-01-31 GB GB311056A patent/GB793860A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3025289A (en) * | 1958-07-12 | 1962-03-13 | Domagk Gerhard | 5-alkoxy-2, 3, 6-trisaziridino-1, 4-benzoquinone |
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