Solid-phase combinatorial syntheses of mesomorphic 4-alkoxyphenyl 4-alkoxybenzoylaminobenzoates

Abstract

Eighteen two-ring and 100 three-ring benzenoid amides were synthesised using a solid-phase combinatorial method involving acylation or benzoylation and palladium(0)-catalysed carbonylation of a secondary amine, obtained by the reductive amination of 4-iodoaniline and a backbone amide linker. The purity of the products obtained was high enough for investigation of their thermal properties. All the three-ring derivatives were shown to be mesomorphic, but the two-ring derivatives were not. The mesomorphic behaviour and the transition temperatures of the three-ring derivatives were virtually identical to those of samples obtained by liquid-phase synthesis and purified by column chromatography and recrystallisation.

Keywords:

• solid-phase combinatorial synthesis
• three-ring benzenoid amides
• reductive amination
• palladium(0)-catalysed carbonylation