Gold-Catalyzed Unexpected Ring Transformation of Pyrimidodiazepine Derivatives

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• 作者：Jaeyoung Koo ; Jonghoon Kim ; Seung Bum Park
• 刊名：Organic Letters
• 出版年：2017
• 出版时间：January 20, 2017
• 年：2017
• 卷：19
• 期：2
• 页码：344-347
• 全文大小：383K
• ISSN：1523-7052

文摘

Pyrimidodiazepine derivatives underwent an unexpected gold-catalyzed retro-Mannich-type carbon–carbon bond cleavage and intramolecular nucleophilic cyclization. The pyrimidodiazepines bearing an alkyne moiety showed novel orthogonal reactivity in the presence of a gold catalyst, as opposed to the alkynophilicity that is commonly observed with gold catalysts. The ring transformation reaction of pyrimidodiazepines probably proceeds through an acyclic iminium intermediate. The potential of this synthetic method for the skeletal diversification of pyrimidine-containing macrocycles was also demonstrated.