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Molecules 2002, 7(2), 119-123; doi:10.3390/70200119

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

Department of Organic Chemistry, Omsk State University, Omsk, 644077, Russian Federation
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Received: 7 May 2001 / Revised: 15 January 2002 / Accepted: 16 January 2002 / Published: 21 February 2002
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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.
Keywords: Darzens reaction; intramolecular cyclization; N-(3-oxoalkyl)chloroacetamides Darzens reaction; intramolecular cyclization; N-(3-oxoalkyl)chloroacetamides
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Fisyuk, A.S.; Poendaev, N.V. Cyclization of N-(3-Oxoalkyl)chloroacetamides Under Basic Conditions. Synthesis of cis-3,4-Epoxypiperidin-2-ones. Molecules 2002, 7, 119-123.

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