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

• DOI: 10.1002/ejoc.201101170
• Publication Date: 2011-09-28T13:50:04Z
• Authors: René den Heeten; Léon J. P. van de...; Daniël L. J. Broere; Elwin Janssen; Frans J. J. de Ka...; Eelco Ruijter; Romano V. A. Orru
• Keywords: 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

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.