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

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-C(6)H(6) solution due to a resulting intramolecular Darzens reaction. It has been found that under kinetically controlled reaction conditions (NaOH/C...

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Detalles Bibliográficos
Autores principales: Fisyuk, Alexander S., Poendaev, Nikolai V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2002
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6146425/
http://dx.doi.org/10.3390/70200119
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author Fisyuk, Alexander S.
Poendaev, Nikolai V.
author_facet Fisyuk, Alexander S.
Poendaev, Nikolai V.
author_sort Fisyuk, Alexander S.
collection PubMed
description 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-C(6)H(6) solution due to a resulting intramolecular Darzens reaction. It has been found that under kinetically controlled reaction conditions (NaOH/C(6)H(6)), besides the intramolecular Darzens reaction an intramolecular alkylation takes place.
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spelling pubmed-61464252018-11-19 Cyclization of N-(3-Oxoalkyl)chloroacetamides Under Basic Conditions. Synthesis of cis-3,4-Epoxypiperidin-2-ones Fisyuk, Alexander S. Poendaev, Nikolai V. Molecules Article 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-C(6)H(6) solution due to a resulting intramolecular Darzens reaction. It has been found that under kinetically controlled reaction conditions (NaOH/C(6)H(6)), besides the intramolecular Darzens reaction an intramolecular alkylation takes place. MDPI 2002-02-28 /pmc/articles/PMC6146425/ http://dx.doi.org/10.3390/70200119 Text en © 2002 by MDPI (http://www.mdpi.org). Reproduction is permitted for non commercial purposes.
spellingShingle Article
Fisyuk, Alexander S.
Poendaev, Nikolai V.
Cyclization of N-(3-Oxoalkyl)chloroacetamides Under Basic Conditions. Synthesis of cis-3,4-Epoxypiperidin-2-ones
title Cyclization of N-(3-Oxoalkyl)chloroacetamides Under Basic Conditions. Synthesis of cis-3,4-Epoxypiperidin-2-ones
title_full Cyclization of N-(3-Oxoalkyl)chloroacetamides Under Basic Conditions. Synthesis of cis-3,4-Epoxypiperidin-2-ones
title_fullStr Cyclization of N-(3-Oxoalkyl)chloroacetamides Under Basic Conditions. Synthesis of cis-3,4-Epoxypiperidin-2-ones
title_full_unstemmed Cyclization of N-(3-Oxoalkyl)chloroacetamides Under Basic Conditions. Synthesis of cis-3,4-Epoxypiperidin-2-ones
title_short Cyclization of N-(3-Oxoalkyl)chloroacetamides Under Basic Conditions. Synthesis of cis-3,4-Epoxypiperidin-2-ones
title_sort cyclization of n-(3-oxoalkyl)chloroacetamides under basic conditions. synthesis of cis-3,4-epoxypiperidin-2-ones
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6146425/
http://dx.doi.org/10.3390/70200119
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