jo4007199_si_001.pdf (2.21 MB)
Iron-Catalyzed Oxidative Tandem Reactions with TEMPO Oxoammonium Salts: Synthesis of Dihydroquinazolines and Quinolines
journal contribution
posted on 2016-02-19, 05:25 authored by Renate Rohlmann, Tobias Stopka, Heinrich Richter, Olga Garcı́a MancheñoA straightforward iron-catalyzed
divergent oxidative tandem synthesis
of dihydroquinazolines and quinolines from N-alkylanilines
using a TEMPO oxoammonium salt as a mild and nontoxic oxidant has
been developed. Fe(OTf)2 was the Lewis acid catalyst of
choice for the formation of dihydroquinazolines, whereas FeCl3 led to better results for the synthesis of quinolines. This
divergent approach implies that, for both syntheses, direct oxidative
functionalization of a α-C(sp3)–H bond of
the N-alkylanilines occurs, leading to C–N
bond formation or C–C bond formation upon homocondensation
or reaction with simple olefins, respectively. Cyclization followed
by a final oxidation generates these classes of interesting bioactive
heterocycles in one synthetic transformation. Additionally, the one-pot
multicomponent synthesis of quinolines from anilines, aldehydes, and
olefins has also been successfully developed under these mild oxidative
conditions.