Synthetic access to new pyridone derivatives through the alkylation reactions of hydroxypyridines with epoxides

General methods for the preparation of a variety of pyridone and oxypyridine derivatives are described. 2-,3-,4-Hydroxy pyridine and 2-pyridinemethanol were alkylated with ethylene-, propylene-, and stryrene-oxide and epichlorohydrin in the presence of different Lewis acids as a catalyst. The best yield of 3a was achieved in the presence of CdI2/BF3·OEt2. The corresponding pyridone derivatives (3a-d, 7a-d) were obtained from the reaction of 2-and 4-hydroxypyridine with oxiranes in good yields, whereas oxypyridine derivatives (5a-d, 9a,b) were obtained from reactions of 3-hydroxypyridine and 2-pyridinemethanol with oxiranes. Chlorohydrines (3d, 5d, 7d) were easily converted to corresponding epoxy derivatives (10, 11, 12) in basic medium; then amino alcohols (13-17) were obtained from the reaction of these epoxy derivatives with amines. Copyright © Taylor & Francis Group, LLC.