Synthesis of 4-Aryl Pyrrolo[1,2-α]quinoxalines via Iron-Catalyzed Oxidative Coupling from an Unactivated Methyl Arene.
J Org Chem
; 86(11): 7390-7402, 2021 06 04.
Article
en En
| MEDLINE
| ID: mdl-34028267
ABSTRACT
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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1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Quinoxalinas
/
Hierro
Idioma:
En
Revista:
J Org Chem
Año:
2021
Tipo del documento:
Article