Product Selectivity Control in the Brønsted Acid-Mediated Reactions with 2-Alkynylanilines

Brønsted acid-catalysed/mediated reactions of the 2-alkynylanilines are reported. While metal-catalysed reactions of these valuable building blocks have led to the establishment of robust protocols for the selective, diverse-oriented syntheses of significant heterocyclic derivatives, we here demonst...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2024-08, Vol.29 (15), p.3693
Main Authors: Morlacci, Valerio, Aschi, Massimiliano, Chiarini, Marco, Momoli, Caterina, Palombi, Laura, Arcadi, Antonio
Format: Article
Language:English
Subjects:
2-alkynylanilines
Acids
annulations
Approximation
Density functionals
DFT calculations
Hydration
Oxidation
sequential reactions
Solvents
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Summary:Brønsted acid-catalysed/mediated reactions of the 2-alkynylanilines are reported. While metal-catalysed reactions of these valuable building blocks have led to the establishment of robust protocols for the selective, diverse-oriented syntheses of significant heterocyclic derivatives, we here demonstrate the practical advantages of an alternative methodology under metal-free conditions. Our investigation into the key factors influencing the product selectivity in Brønsted acid-catalysed/mediated reactions of 2-alkynylanilines reveals that different reaction pathways can be directed towards the formation of diverse valuable products by simply choosing appropriate reaction conditions. The origins of chemo- and regioselectivity switching have been explored through Density Functional Theory (DFT) calculations.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules29153693