Synthesis and reactions of benzannulated spiroaminals: tetrahydrospirobiquinolines
File(s)
Published version
Author(s)
Type
Journal Article
Abstract
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.
Date Issued
2017-07-07
Date Acceptance
2017-05-26
Citation
ACS Omega, 2017, 2 (7), pp.3241-3249
ISSN
2470-1343
Publisher
American Chemical Society
Start Page
3241
End Page
3249
Journal / Book Title
ACS Omega
Volume
2
Issue
7
Copyright Statement
© 2017 American Chemical Society. ACS AuthorChoice - This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html)
Publication Status
Published