Synthesis of aromatic and heteroaromatic oligoamides on methoxypoly(ethylene glycol) as solubilizing polymer support

Abstract

A protecting-group-free procedure for the synthesis of short carbo- and heteroaromatic oligoamide chains on MeO-PEG as solubilizing support is introduced. Starting from nitrocarboxylic acids, oligoamides of carboxylic acids derived from N-methylpyrrole, N-methylimidazole and aniline are synthesized that contain up to five arene units. The polymer support facilitates work up procedures and markedly improves the otherwise poor solubility of the products. Each coupling step is monitored by ¹H-NMR spectroscopy without cleavage of the product from the polymeric support.