synthesis and catalytic functionalization of biologically active indoles

2 Objectives of this Work
This thesis is presented as a cumulative collection of publications that have been
submitted to or are already published in a range of international journals. The
purpose of this summary is to depict the underlying reasons and ideas behind the
journal articles and to clarify the relationship among them.
The major aim of this work was the development of novel indole derivatives and
their catalytic functionalization via palladium catalysis to biologically active 5-HT
receptor ligands. Based on our experience in indole synthesis, our main focus was
the titanium- and zinc-mediated synthesis to substituted indoles and their further
functionalization. We presented for the first time the synthesis of electron-rich
silyloxyindoles via titanium-catalyzed hydrohydrazination of propargyl alcohol
derivatives in Synlett 2007 and the zinc-promoted hydrohydrazination of terminal
alkynes to new indole derivatives in Angew. Chem. Int. Ed 2008.
Furthermore we concentrated on their functionalization via palladium–catalyzed
Buchwald-Hartwig amination reported in Tetrahedron Lett. 2007 and C-O crosscoupling
reaction published in Synthesis 2007.
We investigated a multitude of new complex targets based on the indole skeleton
via cross-coupling reactions, sulfonylation and nucleophilic substitution to new
5-HT receptor ligands published in Org. Biomol. Chem. 2008 and in Eur. J. Org.
Chem. 2008. Additionally, most of the synthesized compounds have been tested
for it’s biologically activity.
Additional achievements in catalytic hydroaminations which have been
investigated during the synthesis of potential biologically active compounds are
reported in Eur. J. Org. Chem. 2007, Tetrahedron 2008, ChemSusChem 2008,
Org. Lett. 2008 and Tetrahedron Lett. 2008. They include improvements and
explorations of methodologies for the synthesis and functionalization of indoles.
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