Universidad de Zaragoza CSIC
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ISQCH - Molecular Activation Through Organometallics (Grupo Consolidado E97)
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Our present research interests are focused on the metal-catalyzed organic synthesis of high added-value products. More specifically, we are interested in the catalyzed synthesis of heterocycles using cheap Ru-complexes. In this area we have developed the synthesis of isoquinolines and other heterocycles, by coupling of primary amines with internal alkynes, as well as the synthesis of isoquinolones and fused pyrones by coupling of primary amides and acids with alkynes. We have also interested in the potential of other donor functional groups as efficient directing groups, beyond N- and O-directing groups. Thus we have achieved the efficient hydroarylation of benzylthioethers, showing the S-directing groups are also compatible with catalytic C-H functionalizations.
In addition, we are developing the synthesis of derivatives of the 1,3-diaminotruxillic acid, due their outstanding interest as agonists of GLP-1 (involved in the treatment of the diabetes type 2) and as antinociceptive drugs (reduction of the sensitivity to painful stimuli by blocking the transmission of electrical signals). We have developed a new method in three steps starting from (Z)-4-aryliden-5(4H)-oxazolones: (i) orthopalladation of the oxazolones by C-H activation; (ii) [2+2]-photochemical cycloaddition of the palladated oxazolones; (iii) hydrogenation and liberation of the 1,3-diaminotruxillic derivatives. In the same line, we are interested in the tailored modification of aminoacids, specially phenylalanine and phenylglycine, and we have performed on these substrates Pd-catalyzed alkenylations, annelations by coupling with internal alkynes, alkoxylations and halogenations.