Abstract
Pyridyl cryptands, such as 12–16 formed from pyridine-2,6-dicarbonyl chloride (4) and crown ether diols 7–11, have been demonstrated to be excellent hosts for viologens (N,N′-dialkyl-4,4′-bipyridinium salts, 2) with Ka values of ∼104 to 106 M−1 and thus are considered to be ideal building blocks for supramolecular systems. However, in order to incorporate these host motifs into useful starting materials, functionalization is required; in this article we describe syntheses of 23 new chelidamic acid (2,6-dicarboxy-4-hydroxypyridine, 5) derivatives that can be used to prepare functional pyridyl cryptands and functional metal ligands. The preparation and characterization of three new functionalized pyridyl cryptands are also included.
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