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

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.