Issue 84, 2014

Unprecedented formation of 2-oxaspiro[bicyclo[2.2.1]heptane-6,3′-indoline] derivatives from reaction of 3-phenacyalideneoxindole with malononitrile or ethyl cyanoacetate

Abstract

The reaction of malononitrile or ethyl cyanoacetate with two molecules of 3-phencylideneoxindoles in ethanol in the presence of piperidine at room temperature afforded novel 7-(1-benzyl-2-oxoindolin-3-yl)-2′-oxo-2-oxaspiro[bicyclo[2.2.1]heptane-6,3′-indoline] derivatives in good yields. Under similar reaction conditions, the reaction of cyanoacetamide with 3-phencylideneoxindoles resulted in polysubstituted 4-(2-oxoindolin-3-yl)-2-oxopyrrolidines. The stereochemistry of the reaction was well established by data from 1H NMR spectra and single crystal structures and a plausible reaction mechanism is rationally proposed.

Graphical abstract: Unprecedented formation of 2-oxaspiro[bicyclo[2.2.1]heptane-6,3′-indoline] derivatives from reaction of 3-phenacyalideneoxindole with malononitrile or ethyl cyanoacetate

Supplementary files

Article information

Article type
Paper
Submitted
26 Jun 2014
Accepted
11 Sep 2014
First published
12 Sep 2014

RSC Adv., 2014,4, 44537-44546

Unprecedented formation of 2-oxaspiro[bicyclo[2.2.1]heptane-6,3′-indoline] derivatives from reaction of 3-phenacyalideneoxindole with malononitrile or ethyl cyanoacetate

Y. Xie, J. Sun and C. Yan, RSC Adv., 2014, 4, 44537 DOI: 10.1039/C4RA06272H

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