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A Convenient Access to 3-(Trihalomethyl)-3-phenyl-3,4-dihydro-2H-1,4-benzÂoxazines/thiazines and Chlorinated 3-Phenyl-2,3-dihydro-1,5-benzoxazepines/thiazepines by an Aziridination-Selective-Ring-Opening Sequence
| Content Provider | Semantic Scholar |
|---|---|
| Author | Shinkevich, Ekaterina Yu. Novikov, Mikhail S. Khlebnikov, Alexander F. |
| Copyright Year | 2007 |
| Abstract | Aziridine ring opening with N-C(1) bond breaking in 1,1-dichloro-1a-phenyl-1a,2-dihydro- 1H-azirino[2,1-c] [ 1,4]benzoxazine and -benzothiazine proceeds under the action of hydrohalo acid to give 3-trihalomethyl derivatives of 1,4-benzoxazine and thiazine. When the same compounds react with boron trifluoride etherate, the ring expansion with N-C(la) bond breaking takes place with formation of 3,4-dichloro-3-phenyl-2,3-dihydro-1,5-benzoxazepine and -1,5-benzothiazepine. These are convenient precursors for the synthesis of 4-substituted 1,5-benzoxazepine and 1,5-benzothiazepine derivatives via reaction with nucleophiles. |
| Starting Page | 225 |
| Ending Page | 230 |
| Page Count | 6 |
| File Format | PDF HTM / HTML |
| DOI | 10.1055/s-2006-958938 |
| Alternate Webpage(s) | http://www.xiuzhengrd.com/ejournals/pdf/synthesis/doi/10.1055/s-2006-958938.pdf |
| Alternate Webpage(s) | https://doi.org/10.1055/s-2006-958938 |
| Volume Number | 2007 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
