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Synthesis of 4-Aryl Pyrrolo[1,2-α]quinoxalines via Iron-Catalyzed Oxidative Coupling from an Unactivated Methyl Arene : Synthesis of 4-Aryl Pyrrolo[1,2-alpha]quinoxalines via Iron-Catalyzed Oxidative Coupling from an Unactivated Methyl Arene
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Cited 16 time in Scopus
- Authors
- Issue Date
- 2021-06
- Publisher
- American Chemical Society
- Citation
- Journal of Organic Chemistry, Vol.86 No.11, pp.7390-7402
- Abstract
- Herein, we describe the direct synthesis of pyrrolo[1,2-alpha]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-alpha]quinoxalines when various methyl arene derivatives were used. The developed method proceeded in air, and all catalysts, reagents, and solvents were easily accessible.
- ISSN
- 0022-3263
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