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Preparation of 4-Alkoxy-1-hydroxypyridine-2-thiones

Jankowiak A., Jakowiecki J., Kaszynski P.

Polish Journal of Chemistry

2007

Vol. 81, nr 11

1869-1877

Reations of 2-chloro-4-fluoropyridine (8), 2-chloro-4-nitropyridine (9), and their corresponding N-oxides 7 and 3 with the n-heptanolate anion were investigated in three solvents. The desired 2-chloro-4-heptyloxypyridine-N-ox ide (4a) was obtained most efficiently from 3 in DMSO. A reaction of 4a with AcSNa followed by deacetylation with MeONa gave the sodium salt of 4-heptyloxy-1-hydroxypyridine-2-thione (1a), which was iso - lated as the adamantane-1-carboxylate O-es ter 2a. Similarly, the 4-decyloxy and 4-((Z)- hex-3-enyloxy) derivatives 2b and 2c were prepared from 3.