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

Molecules

Alexander S. Fisyuk¹ 

[1] Department of Organic Chemistry, Omsk State University, Omsk, 644077, Russian Federation

关键词: Darzens reaction;    intramolecular cyclization;    N-(3-oxoalkyl)chloroacetamides;   

DOI  :  10.3390/70200119

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.