Abstract
2-Hydroxypyridine undergoes a smooth reaction with alkyl propiolates in the presence of triphenylphosphine (15 mol%) to produce the corresponding alkyl 2-[2-oxopyridin-1(2H)-yl]acrylates in good yields. When the reaction was performed by 2-hydroxyquinoline and 2-hydroxyisoquinoline similar α-substituted alkyl acrylates were obtained.
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