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DOI: 10.1055/a-2159-9400
A Golden Synthetic Approach to 2-(1H-Pyrrol-1-yl)anilines and Pyrrolo[1,2-a]quinoxalines through a Gold Carbene Intermediate
N.M. thanks the Türkiye Academy of Sciences Outstanding Young Scientist Award program (TÜBA-GEBİP) and The Scientific and Technological Research Council of Türkiye (TÜBİTAK-121Z727) for grants.
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Abstract
The pyrrolo[1,2-a]quinoxaline skeleton has significant potential for many biological and optical applications. Hence, in this study, unconjugated ynone derivatives were treated with 1,2-diaminoarenes in a gold-catalyzed cyclization to give 2-(1H-pyrrol-1-yl)anilines, which are valuable starting materials, and pyrrolo[1,2-a]quinoxalines by a one-pot and single-step approach. A reaction mechanism for the formation of the pyrrolo[1,2-a]quinoxaline skeleton featuring a key gold carbene intermediate is proposed. On the other hand, the methyl group on the C-2 position of the 2-(1H-pyrrol-1-yl)anilines was oxidized by SeO2 to give the pyrrolo[1,2-a]quinoxaline skeleton, resulting in 14 different pyrrolo[1,2-a]quinoxaline derivatives.
Keywords
pyrroloquinoxalines - diaminoarenes - pyrrolylanilines - gold catalysis - cyclization - oxidationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2159-9400.
- Supporting Information
Publication History
Received: 25 August 2022
Accepted after revision: 24 August 2023
Accepted Manuscript online:
24 August 2023
Article published online:
31 October 2023
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