Gold-Catalyzed Formal [4 + 2] Cycloaddition of 5-(Ethynylamino)pent-2-yn-1-yl Esters to 1,2,3,5-Tetrahydrobenzo[ g]quinolines.
Gold-Catalyzed Formal [4 + 2] Cycloaddition of 5-(Ethynylamino)pent-2-yn-1-yl Esters to 1,2,3,5-Tetrahydrobenzo[ g]quinolines.
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DOI：
10.1021/acs.orglett.8b00267
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发表时间：
2018-02
期刊：
影响因子：
5.2
通讯作者：
Xiaoyu Chen;J. Merrett;Philip Wai Hong Chan
中科院分区：
文献类型：
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作者：
Xiaoyu Chen;J. Merrett;Philip Wai Hong Chan
本发明描述了一种在室温和常压条件下有效制备1，2，3，5-四氢苯并[ g]喹啉的合成方法，该方法依赖于金（I）催化的5-（乙炔基氨基）-2-炔-1-基酯的环化异构化。提出的反应机理提出了一个独特的实例，在原位形成的丙二烯酯和金keteniminium物种进行正式的[4 + 2]环加成途径。
A synthetic method to prepare 1,2,3,5-tetrahydrobenzo[ g]quinolines efficiently that relies on gold(I)-catalyzed cycloisomerization of 5-(ethynylamino)pent-2-yn-1-yl esters at room temperature under atmospheric conditions is described. The proposed reaction mechanism presents a unique instance of an in situ formed allenic ester and gold keteniminium species to undergo a formal [4 + 2] cycloaddition pathway.