Next Article in Journal
Synthesis of 5,6-Dihydropyridin-2(1H)-ones, 1,5,6,8,8a-Hexahydroisoquinolin-3(2H)-ones and 4a,5,6,7,8,8a-Hexahydroquinolin-2(1H)-ones by Intramolecular Wittig Reaction
Previous Article in Journal
Photooxygenation of Nimonol, a Tetranortriterpenoid from Azadirachta indica. A. Juss.
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
Department of Organic Chemistry, Omsk State University, Omsk, 644077, Russian Federation
* Author to whom correspondence should be addressed.
Received: 7 May 2001 / Revised: 15 January 2002 / Accepted: 16 January 2002 / Published: 21 February 2002
Download PDF [26 KB, uploaded 18 June 2014]

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).
SciFeed

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert