Efficient approach to allylated quinolines via palladium-catalyzed cyclization-allylation of 1-azido-2-(2-propynyl) benzenes with allyl methyl carbonate

Jiang Luo, Zhibao Huo, Jun Fu, Fangming Jin, Yoshinori Yamamoto

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The palladium-catalyzed cyclization-allylation reaction of ortho-azido propynylbenzenes 1 and allyl methyl carbonate 2d gives the corresponding allylated quinolines in moderate to good yields. The reaction of 1-azido-2-(2-propynyl)benzene 1a proceeds smoothly with 10 mol % Pd(PPh 3)4 and 5 equiv K3PO4 or NaOAc in DMF at 100 C to afford 3,4-diallylquinoline 3a in 69% yield in the case of R2 = H and 3-allylquinoline 4 in 67% yield in the case of R 2 ≠ H.

Original languageEnglish
Pages (from-to)1552-1556
Number of pages5
JournalTetrahedron Letters
Volume55
Issue number9
DOIs
Publication statusPublished - 2014 Feb 26

Keywords

  • Allylation
  • Cyclization
  • Heterocycles
  • Palladium
  • Synthetic methods

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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