Journal
SYNTHETIC COMMUNICATIONS
Volume 43, Issue 1, Pages 16-25Publisher
TAYLOR & FRANCIS INC
DOI: 10.1080/00397911.2011.589558
Keywords
Beckmann rearrangement; Fischer indolization; Japp-Kilingemann reaction; oxoazacarbazoles; oxocarbazoles; pyrazole; TCT-DMF complex
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Funding
- Department of Science and Technology (DST), New Delhi
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Application of a very mild protocol to the Beckmann rearrangement of ketoximes of pyrazolo annulated oxocarbazole 5a and oxoazacarbazole 5b with the organocatalyst derived from 2,4,6-trichloro[1,3,5] triazine (TCT) and dimethylformamide (DMF) has been explored to provide a regioselective formation of the corresponding azepine 6a and 1,4-diazepine 6b respectively in good yield and purity. The mechanistic precedence for the exclusive formation of only one regioisomer has been discussed.
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