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Synthesis 2009(4): 665-673  
DOI: 10.1055/s-0028-1083342
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Bi- and Tricyclic α,β-Unsaturated Lactams as Potential Michael Acceptors Starting from Heterocyclic Imines

Knut Schulz, Martin Watzke, Katharina Johannes, Pasqual Ullrich, Jürgen Martens*
Institute of Pure and Applied Chemistry, University of Oldenburg, Carl-von-Ossietzky-Straße 9-11, 26129 Oldenburg, Germany
Fax: +49(441)7983757; e-Mail: juergen.martens@uni-oldenburg.de;
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Publication History

Received 25 August 2008
Publication Date:
27 January 2009 (online)

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Abstract

New α,β-unsaturated valerolactams showing potential as Michael acceptors were synthesized from heterocyclic imines as starting materials. The synthetic procedure is based on an acid chloride addition in the first step, followed by a modified Hosomi-Sakurai­ reaction, and a final ring-closing metathesis using a ruthenium catalyst.

Key words

heterocycles - imines - unsaturated lactams - Michael acceptor - ring-closing metathesis

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18

In former investigations using similar substrates, a first-generation Grubbs catalyst showed less activity.¹²

19

CCDC 706274 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.