Concise Synthesis of Highly Substituted Benzo[a]quinolizines by a Multicomponent Reaction/Allylation/Heck Reaction Sequence

Cross-coupling reactions 03 medical and health sciences 0302 clinical medicine Nitrogen heterocycles Multicomponent reactions Medicinal chemistry Polycyclic compounds SDG 6 - Clean Water and Sanitation 01 natural sciences Palladium catalysis 0104 chemical sciences
DOI: 10.1002/ejoc.201101170 Publication Date: 2011-09-28T13:50:04Z
ABSTRACT
AbstractThe combination of the recently developed multicomponent construction of highly substituted 3,4‐dihydropyridones with subsequent allylation and intramolecular Heck‐type cyclization allows the straightforward construction of benzo[a]quinolizines, a class of polycyclic compounds that – despite their interesting pharmacological and photochemical properties – have little precedent in the literature. After optimization of the individual steps, we used this reliable three‐step sequence to generate a small library of diversely substituted benzo[a]quinolizines and various heterocyclic analogs.
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