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Ru-catalyzed coupling reactions for the synthesis of valuable fused heterocycles: primary amides and carboxylic acids as directing groups

AuthorsRuiz Morte, Sara CSIC; Carrera Jiménez, Clara; Villuendas, Pedro CSIC; Urriolabeitia, Esteban P. CSIC ORCID
Issue Date2015
CitationXII Simposio de Investigadores Jóvenes RSEQ Sigma-Aldrich (2015)
AbstractC-H bond activation is a unique tool for the synthesis of relevant molecules which are difficult to obtain by classic synthetic paths1. Heterocyclic compounds can be obtained by metal-­mediated reactions, often catalytically. Thanks to the presence of a directing group, the reaction proceeds with selectivity. Many metals have been used for this purpose, including Pd, Rh and the less‐expensive Ru. Having previously obtained outstanding results using primary amines as directing groups in coupling reactions with alkynes, our group has moved on to explore the reactivity and synthetic possibilities of primary amides. They show some advantages over other directing groups: they are widely available and robust starting materials, and their use avoids the need of manufacturing more complicated groups prior to the C-­H bond functionalization steps. In this way, we have synthesized new, previously unreported heteroarylpyridinones, which possess interesting biological activities. We have also applied this methodology to molecules with O-­containing directing groups to obtain analogous structures. In this case, the coupling of heterocyclic carboxylic acids with internal alkynes yields heteroarylpyranones, which also show promising pharmaceutical activity.
DescriptionResumen del trabajo presentado al XII Simposio de Investigadores Jóvenes de la Real Sociedad Española de Química Sigma-Aldrich, celebrado en Barcelona del 3 al 6 de noviembre de 2015.
Appears in Collections:(ISQCH) Comunicaciones congresos

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