Cyclization of lithiated pyridine and quinoline carboxamides: Synthesis of partially saturated pyrrolopyridines and spirocyclic β-lactams

Jonathan Clayden*, Stuart D. Hamilton, Rukhsana T. Mohammed

*Corresponding author for this work

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

31 Citations (Scopus)

Abstract

(Chemical Equation Presented) Lithiation of N-benzyl pyridine and quinoline carboxamides α to nitrogen gives anions that undergo intramolecular attack on the pyridine or quinoline ring, either directly or on activation of the ring by N-acylation. The resulting four-, five-, or six-membered-ring- containing compound may be oxidized, protonated, alkylated, or acylated to give a range of polycyclic heterocycles, including pyrrolopyridines, pyrroloquinolines, benzonaphthyridines, and azaspirocyclic β-lactams.

Original languageEnglish
Pages (from-to)3673-3676
Number of pages4
JournalOrganic Letters
Volume7
Issue number17
Early online date23 Jul 2005
DOIs
Publication statusPublished - 18 Aug 2005

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