Next Article in Journal
Asymmetric Synthesis of (7aS)-7a-Methyl-4,5,7,7a-tetrahydro-1H-indene-2,6-dione and Useful Derivatives Thereof
Previous Article in Journal
Cytotoxicity of Two Triterpenoids from Nigella glandulifera
Molecules 2006, 11(9), 700-706; doi:10.3390/11090700
Article

An Efficient Synthesis of a Spirocyclic Oxindole Analogue

* ,  and
Department of Chemistry, ChemRoutes Corporation, Edmonton, Alberta T6E 5P8, Canada
* Author to whom correspondence should be addressed.
Received: 13 August 2006 / Revised: 6 September 2006 / Accepted: 14 September 2006 / Published: 14 September 2006
View Full-Text   |   Download PDF [67 KB, uploaded 18 June 2014]   |   Browse Figures

Abstract

An efficient, scaleable synthesis approach towards the spirocyclic oxindole analogue 1’-(tert-butoxycarbonyl)-2-oxospiro[indoline-3,4’-piperidine]-5-carboxylic acid (1) is described. The key steps are dianion alkylation and cyclization of ethyl 2- oxindoline-5-carboxylate (4) and demethylation of the resulting spirocyclic oxindole ethyl 1’-methyl-2-oxospiro[indoline-3,4’-piperidine]-5-carboxylate (5). The target compound was obtained in an overall yield of 35 % over eight steps without resorting to chromatographic purification.
Keywords: Spirocyclic oxindole; dianion alkylation; N-demethylation. Spirocyclic oxindole; dianion alkylation; N-demethylation.
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

Teng, D.; Zhang, H.; Mendonca, A. An Efficient Synthesis of a Spirocyclic Oxindole Analogue. Molecules 2006, 11, 700-706.

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