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DOI: 10.1055/s-0030-1259945
An Efficient Synthesis of 2-Aminofuran-3-carbonitriles via Cascade Stetter-γ-Ketonitrile Cyclization Reaction Catalyzed by N-Heterocyclic Carbene
Publikationsverlauf
Publikationsdatum:
07. April 2011 (online)
Abstract
An efficient method for the synthesis of 4,5-disubstituted 2-aminofuran-3-carbonitriles via a cascade Stetter-γ-ketonitrile cyclization reaction of aromatic aldehydes with acylidenemalononitriles, catalyzed by N-heterocyclic carbenes, has been developed. This procedure provides the corresponding products in moderate to high yields under mild conditions.
Key words
N-heterocyclic carbenes (NHCs) - umpolung - cascade reaction - Stetter reaction - 2-aminofuran
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- Supporting Information
- Primary data for this article are available online and can be cited using the following DOI: 10.4125/pd0010th:
- Primary Data
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References and Notes
General procedure for the synthesis
of 4,5-disubstituted 2-aminofuran-3-carbonitriles 3:
A flame-dried, round-bottom flask was charged with thiazolium salt 4c (0.5 mmol), aromatic aldehyde 1 (1.0 mmol), acylidenemalononitrile 2 (1.0 mmol), and EtOH (5 mL) under a
positive pressure of nitrogen, followed by addition of t-BuOK (1.0 mmol).
The resulting
solution was stirred for 0.5-2 h at r.t. After completion
of the reaction (monitored by TLC), the reaction mixture was concentrated
under reduced pressure. The residue was purified by column chromatography
on silica gel (petroleum ether-EtOAc, 6:1) to afford the
product 3.