Synthesis of Five‐Membered Ring Heteroaryl Pyridines from Heteroaryllithium and N‐Ethoxycarbonylpyridinium Chlorides

Long‐Li ‐L Lai, Li‐Hua ‐H Shin, Pen‐Yuan ‐Y Lin, Jy‐Shih ‐S Wang, Min‐Jen ‐J Shiao

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Abstract

Furylpyridines, thienylpyridines, and imidazolylpyridines were obtained regioselectively in 40‐67% yields from the reaction of heteroaryllithiums with N‐ethoxycarbonylpyridinium chloride or N‐ethoxycarbonyl‐3‐methylpyridinium chloride in the presence of Cul in a catalytic amount at −78 °C or −50°C, then followed by oxidation. The regioselectivity of this reaction depended upon temperature of the reaction and the nature of heteroaryllithiurn.

Original languageEnglish
Pages (from-to)75-79
Number of pages5
JournalJournal of the Chinese Chemical Society
Volume41
Issue number1
DOIs
Publication statusPublished - 1994
Externally publishedYes

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Keywords

  • Furylpyridines
  • Heteroarylpyridines
  • Imidazylpyridines
  • N‐Ethoxycarbonylpyridinium chloride
  • Thienylpyridines

ASJC Scopus subject areas

  • Chemistry(all)

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