New Synthetic Approach for the Incorporation of 3-Hydroxypyridin-2(1H)-one (3,2-HOPO) Ligands: Synthesis of Structurally Diverse Poly 3,2-HOPO Chelators

作者：Arumugam Jayanthi; Brown Hayley A; Jacobs Hollie K^*; Gopalan Aravamudan S

来源：Synthesis, 2011, (1): 57-64.

DOI：10.1055/s-0030-1258337

• 3-hydroxypyridin-2(1H)-one
• synthesis
• polydentate chelators
• mixed ligand chelators
• sulfonamide

The 3,2-HOPO sulfonamide reagent 3 was prepared from commercial 2,3-dihydroxypyridine in four steps in good yields. Sulfonamide 3 readily underwent selective alkylation with dibromides in the presence of base or could be coupled to alcohols using Mitsunobu conditions. The utility of this nucleophilic 3-hydroxypyridin-2(1H)-one (3,2-HOPO) reagent was demonstrated by the synthesis of some tris- and tetrakis-3,2-HOPO chelators. This approach for tethering 3,2-HOPO ligands is unique and flexible as shown by the preparation of 3,2-HOPO/iminocarboxylic acid chelator 17.