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

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

*  and
Received: 7 May 2001; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

AMA Style

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

Chicago/Turabian Style

Fisyuk, Alexander S.; Poendaev, Nikolai V. 2002. "Cyclization of N-(3-Oxoalkyl)chloroacetamides Under Basic Conditions. Synthesis of cis-3,4-Epoxypiperidin-2-ones." Molecules 7, no. 2: 119-123.


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