Organic & Biomolecular Chemistry 2011-05-07

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

Hany F Nour, Marius F Matei, Bassem S Bassil, Ulrich Kortz, Nikolai Kuhnert

Index: Org. Biomol. Chem. 9(9) , 3258-71, (2011)

Full Text: HTML

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 C(3)-symmetrical and non-symmetrical trianglimines. Reduction of the C(3)-symmetrical and the non-symmetrical trianglimines with NaBH(4) in a mixture of THF and MeOH afforded the corresponding trianglamines in high yields.

Related Compounds

  • 4-Bromo-2-fluorobe...

Related Articles:

Synthesis and biological evaluation of 2'-oxo-2,3-dihydro-3'H- spiro[chromene-4,5'-[1,3]oxazolidin]-3'yl]acetic acid derivatives as aldose reductase inhibitors.

2011-06-01

[Arch. Pharm. (Weinheim) 344(6) , 372-85, (2011)]

Benzylamine histamine H(3) antagonists and serotonin reuptake inhibitors.

2007-09-01

[Bioorg. Med. Chem. Lett. 17(17) , 4799-803, (2007)]

The synthesis and biological evaluation of a novel series of antimicrobials of the oxazolidinone class.

2002-08-19

[Bioorg. Med. Chem. Lett. 12(16) , 2121-3, (2002)]

More Articles...