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

Jonathan Clayden, Rachel Turnbull, Ivan Pinto

    Research output: Contribution to journalArticlepeer-review

    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 pages2
    JournalOrganic Letters
    Volume6
    Issue number4
    DOIs
    Publication statusPublished - 19 Feb 2004

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