Tandem Blaise–Nenitzescu reaction: one-pot synthesis of 5-hydroxy-α-(aminomethylene)benzofuran-2(3H)-ones from nitriles?

Organic & Biomolecular Chemistry Pub Date: 2010-11-30 DOI: 10.1039/C0OB01024C

Abstract

In contrast to the reaction of benzoquinones with β-enaminoesters providing indoles (Nenitzescu reaction), the tandem one-pot reaction of the Blaise reaction intermediate, zinc bromide complex of β-enaminoesters, with benzoquinone affords 5-hydroxy-α-(aminomethylene)benzofuran-2(3H)-ones in good to excellent yields (tandem Blaise–Nenitzescu reaction).

Graphical abstract: Tandem Blaise–Nenitzescu reaction: one-pot synthesis of 5-hydroxy-α-(aminomethylene)benzofuran-2(3H)-ones from nitriles
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