Design of a cyclopropyl quinone methide reductive alkylating agent. 2

Omar Khdour, Anlong Ouyang, Edward B. Skibo

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

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 languageEnglish (US)
Pages (from-to)5855-5863
Number of pages9
JournalJournal of Organic Chemistry
Volume71
Issue number16
DOIs
StatePublished - Aug 1 2006

ASJC Scopus subject areas

  • Organic Chemistry

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