Copper-Catalyzed Intramolecular Cyclization of N-Propargyl-Adenine: Synthesis of Purine-Fused Tricyclics

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• 作者：Ren-Long Li ; Lei Liang ; Ming-Sheng Xie ; Gui-Rong Qu ; Hong-Ying Niu ; Hai-Ming Guo
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：April 18, 2014
• 年：2014
• 卷：79
• 期：8
• 页码：3665-3670
• 全文大小：340K
• 年卷期：v.79,no.8(April 18, 2014)
• ISSN：1520-6904

文摘

A novel protocol to construct fluorescent purine-fused tricyclic products via intramolecular cyclization of N-propargyl-adenine has been developed. With CuBr as the catalyst, a series of purine-fused tricyclic products were obtained in good to excellent yields (19 examples, 75鈥?9% yields). When R₂ was a hydrogen atom in N-propargyl-adenines, the reactions only afforded the endocyclic double bond products. When R₂ was an aryl group, the electron-donating groups favored the endocyclic double bond products, while the electron-withdrawing groups favored the exocyclic double bond products.