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Article Abstract

Herein, we describe the direct synthesis of pyrrolo[1,2-α]quinoxaline oxidative coupling between methyl arene and 1-(2-aminophenyl) pyrroles. Oxidation of the benzylic carbon of the methyl arene was achieved by di--butyl peroxide in the presence of an iron catalyst, followed by conversion to an activated aldehyde . 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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http://dx.doi.org/10.1021/acs.joc.1c00371DOI Listing

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