Synthesis and Dynamic NMR Study of Functionalized 1-(3-Furyl)-1<Emphasis Type="Italic">H</Emphasis>-indole-2,3-diones |
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Authors: | Issa Yavari Zinatossadat Hossaini Maryam Sabbaghan |
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Institution: | (1) Department of Chemistry, Tarbiat Modarres University, Tehran, Iran |
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Abstract: | Summary. Protonation of the highly reactive 1:1 intermediates produced in the reaction between alkyl(aryl) isocyanides and dibenzoylacetylene
by isatin, leads to vinylnitrilium cations, which undergo carbon-centered Michael-type addition with the conjugate base of the NH-acid to produce highly functionalized 1-(3-furyl)-1H-indole-2,3-diones. A dynamic NMR effect is observed in the 1H NMR spectra of these compounds as a result of restricted rotation around the single bond linking the indole moiety and the
furan system. The free-energy of activation (ΔG
#) for this process is 69–71 ± 2 kJ mol−1. |
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Keywords: | , Dibenzoylacetylene, Isatin, Alkyl(aryl) isocyanides, Dynamic NMR, |
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