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Cyclization of N-(3-Oxoalkyl)chloroacetamides Under Basic Conditions. Synthesis of cis-3,4-Epoxypiperidin-2-ones

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Author(s): Alexander S. Fisyuk | Nikolai V. Poendaev

Journal: Molecules
ISSN 1420-3049

Volume: 7;
Issue: 2;
Start page: 119;
Date: 2002;
Original page

Keywords: Darzens reaction | intramolecular cyclization | N-(3-oxoalkyl)chloroacetamides

ABSTRACT
It has been shown that N-(3-oxoalkyl)chloroacetamides (1) can be converted into cis-3,4-epoxypiridin-2-ones (2) upon treatment with t-BuOK in a t-BuOH-C6H6 solution due to a resulting intramolecular Darzens reaction. It has been found that under kinetically controlled reaction conditions (NaOH/C6H6), besides the intramolecular Darzens reaction an intramolecular alkylation takes place.
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