Abstract
A cyclopropyl quinone methide is formed by elimination of a leaving group from an appropriately functionalized hydroquinone. The presence of a carbon spacer results in the formation of a fused ring rather than the classic methide species. Discussed herein is cyclopropyl quinone methide formation from a pyrido[1,2-a]indole ring system. Both nucleophilic and electrophilic attack on the fused cyclopropane ring results in pyrido[1,2-a]indole and azepino[1,2-a]indole products. The stereoelectronic effect plays less a role in the relatively flexible pyrido[1,2-a]indole system compared to its role in the pyrrolo[1,2-a]-indole system. A 13C label on the fused cyclopropane ring permitted the rapid identification of complex rearrangement products observed in this study.
Original language | English (US) |
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Pages (from-to) | 5855-5863 |
Number of pages | 9 |
Journal | Journal of Organic Chemistry |
Volume | 71 |
Issue number | 16 |
DOIs | |
State | Published - Aug 1 2006 |
ASJC Scopus subject areas
- Organic Chemistry