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Paper | Regular issue | Vol 75, No. 12, 2008, pp.2949-2958
Published online, 10th July, 2008
DOI: 10.3987/COM-08-11443
A New Approach to the Benzopyridoxepine Core by Metal Mediated Intramolecular Biaryl Ether Formation

Georgeta Serban,* Hitoshi Abe, Yasuo Takeuchi, and Takashi Harayama*

*Faculty of Medicine and Pharmacy, Oradea University, Oradea 410028, Romania

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.