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From Nitrobenzenes to Substituted Tetrahydroquinolines in a Single Step by a Domino Reduction/Imine Formation/Aza-Diels–Alder Reaction

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journal contribution
posted on 20.02.2015 by Hans-Georg Imrich, Jürgen Conrad, Denis Bubrin, Uwe Beifuss
The three-component reaction between a nitrobenzene, an aldehyde, and a dienophile in the presence of iron powder as a reductant and montmorillonite K10 as a catalyst in aqueous citric acid delivers the products of an aza-Diels–Alder (Povarov) reaction with high endo-selectivity and yields up to 99%.