A highly efficient synthesis of 2-[3-aminopropyl]-5,6,7,8-tetrahydronaphthyridine via a double Suzuki reaction and a Chichibabin cyclization

Michael Palucki, David L. Hughes, Nobuyoshi Yasuda, Chunhua Yang, Paul J. Reider

Research output: Contribution to journalArticle

25 Scopus citations

Abstract

Synthesis of 2-[3-aminopropyl]-5,6,7,8-tetrahydronaphthyridine was accomplished via a one-pot double Suzuki reaction followed by deprotection and a highly regioselective intramolecular Chichibabin cyclization. A variety of reactions conditions were screened for the Chichibabin cyclization including choice of base, solvent and reaction temperature.

Original languageEnglish (US)
Pages (from-to)6811-6814
Number of pages4
JournalTetrahedron Letters
Volume42
Issue number39
DOIs
StatePublished - Sep 24 2001
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Keywords

  • Amination
  • Cyclization
  • Naphthyridines
  • Suzuki-Miyaura reactions

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