Science of Synthesis

Spitzner, D., Science of Synthesis, (2005) 15, 21.

The addition of deprotonated methyl ketones to acylketene dithioacetals ‌35‌ is a straightforward procedure for the synthesis of a 1,5-dioxoalkene intermediate which cyclizes in a second step (without workup) with ammonium acetate in glacial acetic acid to provide 4-sulfanylpyridines ‌36‌ (‌Scheme 13‌).[‌75‌] Pyridine–pyrimidine oligomers, e.g. ‌37‌, can be formed similarly (‌Scheme 13‌),[‌76‌–‌79‌] as can terpyridines.[‌80‌] The sulfanyl function can be replaced by a hydrogen using nickel boride.[‌81‌]

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References

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• 8.Meeeee-Meee, (8888) M 8e, 888.