Synthesis and Reactions of Benzannulated Spiroaminals; Tetrahydrospirobiquinolines

DOI: 10.14469/hpc/2099 Metadata

Created: 2017-01-19 16:38

Last modified: 2017-07-17 13:08

Author: Henry Rzepa

Co-author: Joshua Almond-Thynne
Co-author: Anastasios Polyzos
Co-author: Andrew White
Co-author: Anthony Barrett

A efficient two-step synthesis of symmetrical and unsymmetrical tetrahydrospiro-biquinolines from o-azidobenzaldehydes is reported. The previously unreported series of tetrahydrospiro-biquinolines wer accessed through sequential double aldol condensation with acetone, cyclopentanone and cyclohexanone to the corresponding o,o’-diazido-dibenzylidene-acetone, -cyclopentanone and -cyclohexanone derivatives and hydrogenation-spirocyclization. Further elaboration of the spiro-diamines was demonstrated by electrophilic aromatic bromination, Suzuki coupling and N-alkylation, which all proceeded with preservation of the spirocyclic core.

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SupportingInformation_ACSOmega.pdf 4MB application/pdf Supporting information for synthetic procedures.

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DOIDescription
10.14469/hpc/2098 Computational data for Synthesis and Reactions of Benzannulated Spiroaminals; Tetrahydrospirobiquinolines
10.14469/hpc/2294 NMR data for Synthesis and Reactions of Benzannulated Spiroaminals; Tetrahydrospirobiquinolines
10.14469/hpc/2297 Crystal structure data for Synthesis and Reactions of Benzannulated Spiroaminals; Tetrahydrospirobiquinolines

Associated DOIs

DOIDescription
10.1021/acsomega.7b00482 published article on Synthesis and Reactions of Benzannulated Spiroaminals; Tetrahydrospirobiquinolines

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