N N-Formamido-Containing Mono- and Diheterocyclic Pyrrole- and Imidazole-2-carboxylic Acids as Building Blocks for Polyamide Synthesis
Mulder, K.; Sexton, J. S.; Taherbhai, Z. T.; Jones, J. B.; Uthe, P. B.; Brown, T.; Lee, M. N N-Formamido-Containing Mono- and Diheterocyclic Pyrrole- and Imidazole-2-carboxylic Acids as Building Blocks for Polyamide Synthesis. Synth. Commun. 2007, 38, 33-44.
Four Nâ€formamidoâ€containing monoâ€and diheterocyclic pyrroleâ€ and imidazoleâ€2â€containing acids 1â€“4 were synthesized as intermediates for the preparation of polyamide molecules. The Nâ€formamidoâ€moiety forces the compounds to bind strongly as a stacked dimer, and in a staggered fashion, at specific sequences in the minorâ€groove of DNA. The acid moiety at the Câ€terminus of compounds enables these molecules to be coupled to amineâ€containing intermediates to form the amide linkages of the target polyamide. This convergent approach increases the synthetic diversity in polyamide chemistry by enabling one acid to be used with a variety of different Câ€terminusâ€functionalized intermediates.