Design of a cyclopropyl quinone methide reductive alkylating agent. 2

Omar Khdour, Anlong Ouyang, Edward B. Skibo

Research output: Contribution to journalArticle

18 Citations (Scopus)

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

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Alkylating Agents
Labels
Carbon
indole
quinone methide
cyclopropane

ASJC Scopus subject areas

  • Organic Chemistry

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Design of a cyclopropyl quinone methide reductive alkylating agent. 2. / Khdour, Omar; Ouyang, Anlong; Skibo, Edward B.

In: Journal of Organic Chemistry, Vol. 71, No. 16, 01.08.2006, p. 5855-5863.

Research output: Contribution to journalArticle

Khdour, Omar ; Ouyang, Anlong ; Skibo, Edward B. / Design of a cyclopropyl quinone methide reductive alkylating agent. 2. In: Journal of Organic Chemistry. 2006 ; Vol. 71, No. 16. pp. 5855-5863.
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