Preparation of peri-annulated indoles from polynitro compounds

A novel peri-annulated heterocyclic system of 1,2-dihydrobenz[6,7]oxepino[4,3,2- cd]indole was prepared starting from TNT via 4,6-dinitro-1-tosylindoline as a key intermediate. Base-induced C C bond shift in 1,2-dihydrobenz[6,7]oxepino[4,3,2- cd]indoles affords isomeric 2,11-dihydrobenz[6,7]oxepino[...

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Bibliographic Details
Published in:Tetrahedron 2009-08, Vol.65 (34), p.6868-6872
Main Authors: Samet, Alexander V., Yamskov, Alexei N., Strelenko, Yuri A., Semenov, Victor V.
Format: Article
Language:English
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Summary:A novel peri-annulated heterocyclic system of 1,2-dihydrobenz[6,7]oxepino[4,3,2- cd]indole was prepared starting from TNT via 4,6-dinitro-1-tosylindoline as a key intermediate. Base-induced C C bond shift in 1,2-dihydrobenz[6,7]oxepino[4,3,2- cd]indoles affords isomeric 2,11-dihydrobenz[6,7]oxepino[4,3,2- cd]indoles. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.06.074