A transfer hydrogenative condensation between 2-nitroanilines and vicinal diols for the synthesis of quinoxalines, with no additional oxidant, reductant and base.
Herein, we describe the direct synthesis
of pyrrolo[1,2-α]quinoxaline via oxidative
coupling between methyl arene and 1-(2-aminophenyl)
pyrroles. Oxidation of the benzylic carbon of the methyl arene was
achieved by di-t-butyl peroxide in the presence of
an iron catalyst, followed by conversion to an activated aldehyde in situ. Oxygen played a crucial role in the oxidation process
to accelerate benzaldehyde formation. Subsequent Pictet–Spengler-type
annulation completed the quinoxaline structure. The protocol tolerated
various kinds of functional groups and provided 22 4-aryl pyrrolo[1,2-α]quinoxalines
when various methyl arene derivatives were used. The developed method
proceeded in air, and all catalysts, reagents, and solvents were easily
accessible.
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