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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Heterocycles via SiCl4-Promoted Isocyanide Additions to Oxonitriles
John Kornfeind1, James E Allen1, Taylor M Keller1
1Department of Chemistry, Drexel University, 3401 Chestnut Street, Philadelphia, Pennsylvania 19104, United States.
Abstract:
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.
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