Gram Scale Synthesis of Membrane-Active Antibacterial 4-Quinolone Lead Compound

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Abstract

An improved method for the synthesis of a new quinolone class of antibiotics, which are exceptionally potent against gram-positive bacteria, has been developed and the structure confirmed by single-crystal X-ray analysis. In the course of synthesis, using either Chan-Lam coupling or Buchwald-Hartwig amination, we have shown that the careful choice of protecting group at the C4 position of the quinoline is required for selective amination at the C5 position and subsequent deprotection to avoid the formation of a novel pyrido[4,3,2-de]quinazoline tetracycle.

Original languageEnglish (US)
Pages (from-to)6209-6217
Number of pages9
JournalJournal of Organic Chemistry
Volume88
Issue number9
DOIs
StatePublished - May 5 2023

Bibliographical note

Publisher Copyright:
© 2023 American Chemical Society.

PubMed: MeSH publication types

  • Journal Article
  • Research Support, N.I.H., Extramural

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