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

doi:10.3390/70200119

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

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

Alexander S. Fisyuk* and Nikolai V. Poendaev

Department of Organic Chemistry, Omsk State University, Omsk, 644077, Russian Federation

* Author to whom correspondence should be addressed.

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

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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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