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The use of enaminones in Buchwald-Hartwig cross-coupling: Synthesis of tetrahydroquinoline derivatives

Authors: Doušová Hana | Horák Radim | Šimůnek Petr | Růžičková Zdeňka

Year: 2016

Type of publication: ostatní - přednáška nebo poster

Page from-to: nestránkováno

Titles:

Language	Name	Abstract	Keywords
eng	The use of enaminones in Buchwald-Hartwig cross-coupling: Synthesis of tetrahydroquinoline derivatives	Corresponding enaminones 2 containing both the primary and secondary amino group were synthesized from the appropriate β-diketones 1 (prepared by Claisen condensation) by the reaction with ammonium acetate or primary amine. On the basis of a broad optimization study (changing the ligands, catalysts, bases and solvents), the suitable reaction conditions for N-arylation of the enaminones were found. The synthesis of 2-aroylmethylidene-1,2,3,4-tetrahydroquinolines 3 was previously described in the literature with unsatisfactory yields (~19 %). Our approach is superior and much more effective (yields 45 – 96 %). The extension of this methodology is now being in progress in our laboratory.