Synthesis of Linker Isomers of Quinolin-6-yloxyacetamide Fungicides through Newman–Kwart Rearrangement

Novel quinolin-6-ylthioacetamides and quinolin-6-ylpropanamides have been prepared. They are linker isomers of quinolin-6-yloxyacetamide fungicides in which the oxygen atom of the O,S-acetal in the original lead structures has been replaced by either a sulfur atom or a methylene bridge. The Newman-Kwart rearrangement proved to be highly useful for the concise synthesis of the quinolin-6-ylthioacetamides from available quinolinol building blocks.