Lewis acid-promoted cascade reaction of primary amine, 2-butynedioate, and propargylic alcohol: A convenient approach to 1,2-dihydropyridines and 1H-pyrrolo[3,4-b]pyridine-5,7(2H,6H)-diones

摘要

1,2-Dihydropyridine-5,6-dicarboxylates were efficiently constructed through a cascade reaction of primary amine, 2-butynedioate and propargylic alcohol in the presence of Lewis acid under mild conditions. As exceptional, 1H-pyrrolo[3,4-b]pyridine-5,7(2H,6H)-diones were approached when the primary amine was methylamine. Possible mechanism for the formation of 1,2-dihydropyridine skeleton is proposed. The process involves 1,3,4-pentatrien-1-amine as a key intermediate that formed in situ by trapping allenic carbocations with enamines.