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Issue 9, 2011
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Synthesis of tri-substituted biaryl based trianglimines: formation of C3-symmetrical and non-symmetrical regioisomers

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Abstract

2-Functionalised aromatic monoaldehydes were synthesised in good to excellent yields by reacting 4-bromo-2-fluorobenzaldehyde with different secondary amines and phenol. The Suzuki-coupling reaction of the newly functionalised aromatic monoaldehydes with 4-formylphenylboronic acid afforded the corresponding 2-functionalised-4,4′-biphenyldialdehydes in good yields (47–85%). The [3+3]-cyclocondensation reactions of the 2-functionalised-4,4′-biphenyldialdehydes with (1R,2R)-1,2-diaminocyclohexane afforded a mixture of regioisomeric C3-symmetrical and non-symmetrical trianglimines. Reduction of the C3-symmetrical and the non-symmetrical trianglimines with NaBH4 in a mixture of THF and MeOH afforded the corresponding trianglamines in high yields.

Graphical abstract: Synthesis of tri-substituted biaryl based trianglimines: formation of C3-symmetrical and non-symmetrical regioisomers

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Supplementary files

Article information


Submitted
27 Oct 2010
Accepted
06 Jan 2011
First published
23 Mar 2011

Org. Biomol. Chem., 2011,9, 3258-3271
Article type
Paper

Synthesis of tri-substituted biaryl based trianglimines: formation of C3-symmetrical and non-symmetrical regioisomers

H. F. Nour, M. F. Matei, B. S. Bassil, U. Kortz and N. Kuhnert, Org. Biomol. Chem., 2011, 9, 3258 DOI: 10.1039/C0OB00944J

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