Next Article in Journal
Previous Article in Journal
Molecules 2006, 11(9), 700-706; doi:10.3390/11090700
Article

An Efficient Synthesis of a Spirocyclic Oxindole Analogue

* ,  and
Received: 13 August 2006; in revised form: 6 September 2006 / Accepted: 14 September 2006 / Published: 14 September 2006
Download PDF [67 KB, uploaded 18 June 2014]
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Export to BibTeX |
EndNote


MDPI and ACS Style

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

AMA Style

Teng D, Zhang H, Mendonca A. An Efficient Synthesis of a Spirocyclic Oxindole Analogue. Molecules. 2006; 11(9):700-706.

Chicago/Turabian Style

Teng, Dawei; Zhang, Hongxing; Mendonca, A. 2006. "An Efficient Synthesis of a Spirocyclic Oxindole Analogue." Molecules 11, no. 9: 700-706.


Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert