Gold(I)-catalyzed synthesis of N -alkenyl 2-pyridonyl sec -amines

-Alkenyl 2-pyridonyl amines are afforded in high yields a gold-catalyzed rearrangement of 2-propargyloxypyridine and 2-(but-3-yn-1-yloxy)pyridine under acidic conditions. This approach exhibits significant utility due to its outstanding efficiency of conversion in the synthesis of secondary amines a...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2024-07, Vol.22 (27), p.5646-5652
Main Author: Karatavuk, Ali Osman
Format: Article
Language:English
Subjects:
Amines
Aniline
Chemical synthesis
Gold
Pyridines
Pyridinium
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Summary:-Alkenyl 2-pyridonyl amines are afforded in high yields a gold-catalyzed rearrangement of 2-propargyloxypyridine and 2-(but-3-yn-1-yloxy)pyridine under acidic conditions. This approach exhibits significant utility due to its outstanding efficiency of conversion in the synthesis of secondary amines as a one-pot reaction. The initial step of the method involves a cyclization reaction for the production of pyridinium salts, followed by the next stage, where rearrangement is accomplished through the nucleophilic addition phenomenon. This approach provides the conversion of primary amines into secondary amines, resulting in a single product. Furthermore, the methodology presents a high degree of tolerance towards several pyridine and aniline derivatives, resulting in the formation of products with excellent yields.
ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/d4ob00815d