Nucleophilic Addition to Electron-Rich Heteroaromatics: Dearomatizing Anionic Cyclizations of Pyrrolecarboxamides

Jonathan Clayden*, Rachel Turnbull, Ivan Pinto

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

31 Citations (Scopus)

Abstract

(Matrix presented) Despite its electron-rich nature, a pyrrole ring is susceptible to intramolecular nucleophilic attack by organolithiums. The resulting dearomatizing anionic cyclization yields new 5- or 7-membered heterocyclic rings. Formation of a new 5-membered ring, by cyclization of an N-benzylpyrrolecarboxamide, is accompanied by ring opening of the original pyrrole to yield 3-aminovinylpyrrolinones. Formation of a new 7-membered ring, by cyclization of an N-allyl pyrrolecarboxamide, yields bicyclic pyrroloazepinones.

Original languageEnglish
Pages (from-to)609-611
Number of pages3
JournalOrganic Letters
Volume6
Issue number4
Early online date24 Jan 2004
DOIs
Publication statusPublished - 19 Feb 2004

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