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

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• 作者：Guangwei Yin ; Yuanxun Zhu ; Ningning Wang ; Ping Lu ; Yanguang Wang
• 关键词：Cascade reactions ; Dihydropyridines ; Heterocycles ; Propargylic alcohols ; Lewis acid
• 刊名：Tetrahedron
• 出版年：2013
• 出版时间：30 September, 2013
• 年：2013
• 卷：69
• 期：39
• 页码：8353-8359
• 全文大小：651 K

文摘

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.