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
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote
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

Comments

Citing Articles

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