Abstract
AbstractSeveral salen‐type ligands functionalized with two pyrrole derivative pendant arms were prepared. These Schiff base ligands, which differ in the imine bridge, were prepared by a multi‐step procedure that includes (i) synthesis of 3‐pyrrol‐1‐ylpropanoic acid, (ii) transformation of the latter compound into the mixed carboxylic–carbonic anhydride (MCCA) intermediate followed by reaction with 2,3‐dihydroxybenzaldehyde to give (3‐formyl‐2‐hydroxyphenyl) 3‐(pyrrol‐1‐yl)propanoate and finally (iii) Schiff condensation of the different 1,2‐diamines with (3‐formyl‐2‐hydroxyphenyl) 3‐(pyrrol‐1‐yl)propanoate. The key step in the Schiff base ligand preparation is the functionalization of the 2,3‐dihydroxybenzaldehyde at the C‐3 hydroxyl group without protection of the C‐2 hydroxyl group, by a regiospecific acylation of the ortho‐hydroxyl group via esterification with the mixed carboxylic–carbonic anhydride of 3‐pyrrol‐1‐ylpropanoic acid. The compounds were characterized by elemental analyses, 1H and 13C NMR spectroscopy, mass spectrometry and FTIR and UV–visible spectrophotometry. Copyright © 2005 John Wiley & Sons, Ltd.
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