An Efficient Synthesis of a Spirocyclic Oxindole Analogue

doi:10.3390/11090700

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Molecules 2006, 11(9), 700-706; doi:10.3390/11090700

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An Efficient Synthesis of a Spirocyclic Oxindole Analogue

Dawei Teng* , Hongxing Zhang and A. Mendonca

Department of Chemistry, ChemRoutes Corporation, Edmonton, Alberta T6E 5P8, Canada

* Author to whom correspondence should be addressed.

Received: 13 August 2006; in revised form: 6 September 2006 / Accepted: 14 September 2006 / Published: 14 September 2006

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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.

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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.

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