3-Alkenyltyrosines Accessed by Suzuki-Miyaura Coupling: A Key Intermediate in the Synthesis and Mechanistic Study of Povarov Multicomponent Reactions
3-Vinyl and 3-stilbenyl tyrosine derivatives, accessed by the Suzuki-Miyaura coupling reaction in good yields, are presented. These synthetic olefins then provided a fast and effective synthesis of functionalized quinolines by a silver-catalyzed, microwave-mediated Povarov reaction in just 40min. In...
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Published in | Asian journal of organic chemistry Vol. 6; no. 7; pp. 913 - 920 |
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Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
Published |
WEINHEIM
Wiley
01.07.2017
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Subjects | |
Online Access | Get more information |
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Summary: | 3-Vinyl and 3-stilbenyl tyrosine derivatives, accessed by the Suzuki-Miyaura coupling reaction in good yields, are presented. These synthetic olefins then provided a fast and effective synthesis of functionalized quinolines by a silver-catalyzed, microwave-mediated Povarov reaction in just 40min. In addition, we demonstrate a tandem one-pot microwave-mediated Povarov-CuAAC (copper-catalyzed azide-alkyne cycloaddition) synthesis to provide a 1,2,3-triazole ring with 35% overall yield. We propose a Povarov/aromatization mechanism, based on high-resolution mass spectrometry experiments, combined with computational studies based on density functional theory (DFT) methods. |
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Bibliography: | FAPESP |
ISSN: | 2193-5807 2193-5815 |
DOI: | 10.1002/ajoc.201700154 |