Condensed Heteroaromatic Ring Systems. VII.1) Synthesis of Thienopyridines, Thienopyrimidines, and Furopyridines from o-Substituted N-Heteroarylacetylenes

Takao Sakamoto, Yoshinori Kondo, Ryô Watanabe, Hiroshi Yamanaka

Research output: Contribution to journalArticlepeer-review

49 Citations (Scopus)

Abstract

The cross-coupling reaction of 2-chloro-3-iodo- and 4-chloro-3-iodopyridines with phenyl-acetylene in the presence of dichlorobis(triphenylphosphine)palladium occurred at the 3-position. The 3-ethynylpyridines containing an adjacent chloro group were convertible to thienopyridines by treatment with sodium hydrosulfide. Similarly, various thieno[2,3-d]pyrimidines were synthesized from 4-chloro-5-iodopyrimidines. One-step synthesis of furopyridines by the palladium-catalyzed reaction of iodohydroxypyridines with terminal acetylenes is also described.

Original languageEnglish
Pages (from-to)2719-2724
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume34
Issue number7
DOIs
Publication statusPublished - 1986 Jan 1

Keywords

  • Chloroiodopyridine
  • Chloroiodopyrimidine
  • acetylene
  • furopyridine
  • hydroxyiodopyridine
  • palladium-catalyzed reaction
  • thienopyridine
  • thienopyrimidine

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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