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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Bibliographic Details
Published inAsian journal of organic chemistry Vol. 6; no. 7; pp. 913 - 920
Main Authors Vasconcelos, Stanley N. S., Menezes da Silva, Vitor H., Braga, Ataualpa A. C., Shamim, Anwar, Souza, Frederico B., Pimenta, Daniel C., Stefani, Helio A.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.07.2017
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
multicomponent reactions
CATALYSIS
stilbene
QUINOLINES
REACTIVITY
quinoline
mechanistic investigations
tyrosine
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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.
Bibliography:FAPESP
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201700154