Synthesis and Reactions of Benzannulated Spiroaminals: Tetrahydrospirobiquinolines
Joshua Almond-Thynne, Andrew JP White, Anastasios Polyzos, Henry S Rzepa, Philip J Parsons, Anthony GM Barrett
ACS OMEGA | AMER CHEMICAL SOC | Published : 2017
An efficient two-step synthesis of symmetrical and unsymmetrical tetrahydrospirobiquinolines from o-azidobenzaldehydes is reported. A novel series of tetrahydrospirobiquinolines was prepared by sequential double-aldol condensation with acetone, cyclopentanone, and cyclohexanone to form the corresponding o,o'-diazido-dibenzylidene-acetone, -cyclopentanone, and -cyclohexanone derivatives, respectively, and hydrogenation-spirocyclization. The spirodiamines were further derivatized by electrophilic aromatic bromination, Suzuki coupling, and N-alkylation, all of which proceeded with preservation of the spirocyclic core.