Science of Synthesis

Spitzner, D., Science of Synthesis, (2005) 15, 86.

Carbonylation of 3-azapenta-1,3-dienes [(vinylimino)alkanes] with bis(1H-imidazol-1-yl) ketone gives pyridin-4-ols [pyridin-4(3H)-ones].[‌374‌] The same 3-azapenta-1,3-dienes ‌321‌, however, react with thiophosgene to give an intermediate 6,6-dichloro-3-azahexa-1,3,5-triene which cyclizes (elimination of HCl) to the corresponding 4-chloropyridines ‌322‌ (‌Scheme 105‌).[‌375‌]

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References

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• 8.Meeeee-Meee, (8888) M 8e, 888.