Abstract
A novel preparation of 5-functionalised pyridine derivatives is reported from 5-bromo-4-tosyloxypyridines via a Br/Mg exchange procedure with i-PrMgCl·LiCl, followed by addition of an electrophile. The reaction was carried out under mild conditions and gave good to high yields. The resulting 5-functionalised pyridine derivatives enrich the library of pyridinone-type iron-chelator prodrugs.
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