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

doi:10.1039/C4RA06272H

Paper

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

Published Sep 17, 2014 · Ya-Jing Xie, Jing Sun, Chaoguo Yan

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14

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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.

Study Snapshot

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

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

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

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