Synthesis and Reactions of Benzannulated Spiroaminals; Tetrahydrospirobiquinolines
DOI: 10.14469/hpc/2099 Metadata
Created: 2017-01-19 16:38
Last modified: 2022-04-22 12:26
License: Creative Commons: Public Domain Dedication 1.0
Funding: (none given)
Co-author: Joshua Almond-Thynne Co-author: Anastasios Polyzos Co-author: Andrew White Co-author: Anthony Barrett
Description
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,oâ-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.
Files
Filename | Size | Type | Description |
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SupportingInformation_ACSOmega.pdf | 4MB | application/pdf | Supporting information for synthetic procedures. |
Members
DOI | Description |
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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
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References | 10.1021/acsomega.7b00482 | published article on Synthesis and Reactions of Benzannulated Spiroaminals; Tetrahydrospirobiquinolines |