Regioselective Synthesis of Oxepin- and Oxocin-Annulated Quinolines by Combined ‘Claisen-Rearrangement/Olefin-Metathesis’ Reactions

Sven Rotzoll; Helmar Görls; Peter Langer

doi:10.1055/s-2007-990949

PAPER

Regioselective Synthesis of Oxepin- and Oxocin-Annulated Quinolines by Combined ‘Claisen-Rearrangement/Olefin-Metathesis’ Reactions

Sven Rotzoll^a,b, Helmar Görls^c, Peter Langer*^a,b
^a Institut für Chemie, Universität Rostock, Albert Einstein Str. 3a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: Peter.Langer@uni-rostock.de;
^b Leibniz-Institut für Katalyse, Universität Rostock e.V., Albert Einstein Str. 29a, 18059 Rostock, Germany
^c Institut für Anorganische und Analytische Chemie, Universität Jena, August-Bebel-Str. 2, 07740 Jena, Germany

Abstract

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Abstract

Oxepin- and oxocin-fused quinolines were prepared by a combined Claisen-rearrangement/ring-closing metathesis approach. The metathesis reactions proceeded in good yields despite the presence of the lone pair of the nitrogen atom of the quinoline moiety. The formation of a hydrochloride salt was not necessary.

Key Words

cyclization - heterocycles - rearrangement - ring-closing metathesis

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References

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