American Chemical Society
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Heterocycles via SiCl4‑Promoted Isocyanide Additions to Oxonitriles

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posted on 2023-11-08, 16:35 authored by John Kornfeind, James E. Allen, Taylor M. Keller, Fraser F. Fleming
SiCl4 promotes isocyanide additions to oxoalkenenitriles to selectively generate 3-acylpyrroles, 2-aminofurans, or pyrrolidinones. Cyclic oxoalkenenitriles add 2 equiv of an isocyanide that installs the two core atoms of an acylpyrrole and a nitrile substituent, whereas acyclic oxoalkenenitriles add 1 equiv of an isocyanide to afford 2-aminofurans; subsequent air oxidation generates pyrrolidinones via a furan oxygenation–cleavage–cyclization sequence. The syntheses proceed under mild conditions to rapidly access three richly decorated heterocycles.