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DOI: 10.1055/s-0028-1083537
Novel Extensions of the tert-Amino Effect: Formation of Phenanthridines and Diarene-Fused Azocines from ortho-ortho′-Functionalized Biaryls
Publication History
Publication Date:
15 October 2008 (online)
Abstract
Phenanthridines and azocines fused to two benzene rings or one benzene and one pyridazinone ring, which are otherwise difficult to access, were prepared via two new extensions of the tert-amino effect. The synthetic pathway includes three steps: i) Suzuki reaction of an ortho-functionalized phenylboronic acid with ortho-disubstituted benzenes or pyridazinones; ii) the Knoevenagel condensation reaction of the biaryl aldehydes formed with active methylene compounds to obtain vinyl derivatives or, through their cyclization, phenanthridines via a tert-amino effect; and iii) thermal isomerization of vinyl or phenanthridinium compounds to fused azocines via another type of tert-amino effect.
Key words
tert-amino effect - dibenzazocines - pyridazinobenzazocines - nonbonding interactions - Suzuki reaction
- Supporting Information for this article is available online:
- Supporting Information
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References and Notes
The X-ray data are available from the Cambridge Crystallographic Data Centre CCDC under the numbers 692718-692722 for 7b, 13a, 16c, 19a, and 23a, respectively. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336033 or e-mail: deposit @ccdc.cam.ac.uk. The details of the X-ray structures will be published elsewhere.
14Dunkel, P.; Földi, Á. A.; Mátyus, P. unpublished results.
15The experimental details are available in the Supporting Information.