Direct Construction of Bicyclic Heterocycles by Palladium-Catalyzed Domino Cyclization of Propargyl Bromides

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• 作者：Hiroaki Ohno ; Akinori Okano ; Shohei Kosaka ; Koji Tsukamoto ; Miyo Ohata ; Kotaro Ishihara ; Hatsuo Maeda ; Tetsuaki Tanaka ; Nobutaka Fujii
• 刊名：Organic Letters
• 出版年：2008
• 出版时间：March 20, 2008
• 年：2008
• 卷：10
• 期：6
• 页码：1171 - 1174
• 全文大小：95K
• 年卷期：v.10,no.6(March 20, 2008)
• ISSN：1523-7052

文摘

The palladium-catalyzed domino cyclization of propargyl bromides having two nucleophilic functional groups is described. Treatment of 1,7-diamino-5-bromohept-3-yne derivatives with catalytic Pd(PPh₃)₄ in the presence of NaH in MeOH gives the 2,7-diazabicyclo[4.3.0]non-5-enes ingood yields. Interestingly, the regioselectivity of the reaction is completely controlled by the relative reactivity of the amine functional groups,irrespective of the position of the nucleophiles. The malonate derivative also undergoes domino cyclization to produce a hexahydroindolederivative.