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An Intramolecular Buchwald-Hartwig Cross-coupling Reaction: A Powerful Tool In Synthesis Of Cyclic Enaminones

Authors: Doušová Hana | Šimůnek Petr | Růžičková Zdeňka

Year: 2017

Type of publication: ostatní - přednáška nebo poster

Page from-to: nestránkováno

Titles:

Language	Name	Abstract	Keywords
eng	An Intramolecular Buchwald-Hartwig Cross-coupling Reaction: A Powerful Tool In Synthesis Of Cyclic Enaminones	Our group has been interested in exploring the synthetic potential of enaminones for many years. These versatile and readily obtainable compounds could be the direct precursors of some biologically active substances1 (e.g. alkaloids 3 from Galipea Officinalis). We developed a simple and efficient methodology for an intramolecular, particularly palladium, but also copper catalysed amination of chloro or bromo substituted non-cyclic enaminones 1a,b leading to the tetrahydroquinoline moiety2 2a or derivatives of tetrahydro/dihydrothienopyridine 2b. On the basis of wide optimization study (changing the ligands, catalysts, bases and solvents), we were able to prepare a library of cyclic enaminones 2a,b in up to 98 % yield. In this work, a new approach to cyclic enaminones using C–N cross-coupling reaction was introduced and an extension of this methodology is now being in progress in our laboratory.	Buchwald-Hartwig; cyclic enaminones; copper; catalyse