A new approach to the benzopyridoxepine core by metal mediated intramolecular biaryl ether formation

Georgeta Serban, Hitoshi Abe, Yasuo Takeuchi, Takashi Harayama

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

This paper presents a concise synthesis of the novel [1,3]dioxo[d]benzoxepino[2,3-c]-6-bromopyridine 1. The benzopyridoxepine core has been obtained by intramolecular coupling of a benzopyridylethene that is in turn obtained from the Wittig reaction. Thus, the synthesis was accomplished in a very good yield by implementation of an intramolecular palladium-catalyzed biaryl ether formation (Buchwald-Hartwig type reaction). An alternative approach based on the copper-mediated C-O bond formation (intramolecular Ullmann reaction) was not successful.

Original languageEnglish
Pages (from-to)2949-2958
Number of pages10
JournalHeterocycles
Volume75
Issue number12
DOIs
Publication statusPublished - Dec 1 2008

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Palladium
Ether
Copper
Metals

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Pharmacology

Cite this

A new approach to the benzopyridoxepine core by metal mediated intramolecular biaryl ether formation. / Serban, Georgeta; Abe, Hitoshi; Takeuchi, Yasuo; Harayama, Takashi.

In: Heterocycles, Vol. 75, No. 12, 01.12.2008, p. 2949-2958.

Research output: Contribution to journalArticle

Serban, Georgeta ; Abe, Hitoshi ; Takeuchi, Yasuo ; Harayama, Takashi. / A new approach to the benzopyridoxepine core by metal mediated intramolecular biaryl ether formation. In: Heterocycles. 2008 ; Vol. 75, No. 12. pp. 2949-2958.
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