Concise synthesis of highly substituted benzo[a]quinolizines by a multicomponent reaction/allylation/heck reaction sequence

Journal article

The 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. Copyright © 2012 WILEY-VCH Verlag GmbH and Co. KGaA, Weinheim.

Authors: Den Heeten, R; Van Der Boon, L; Broere, D; Janssen, E; De Kanter, F

• Journal: European Journal of Organic Chemistry
• Volume: 2012
• Issue: 2
• Pages: 275-280
• Publication date: 2012-01-01
• DOI: 10.1002/ejoc.201101170
• EISSN: 1099-0690
• ISSN: 1434-193X
• Language: English
• Keywords: Cross-coupling reactions; Palladium catalysis; Multicomponent reactions; Nitrogen heterocycles; Medicinal chemistry; Polycyclic compounds