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金催化的涉及[3+2+2]环加成反应合成3,4-稠合双环/三环呋喃的串联环化反应

Gold-catalyzed sequential annulations towards 3,4-fused bi/tri-cyclic furans involving a [3+2+2]-cycloaddition.

作者信息

Liu Suna, Yang Pu, Peng Shiyong, Zhu Chenghao, Cao Shengyu, Li Jian, Sun Jiangtao

机构信息

Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, and School of Pharmaceutical Engineering & Life Science, Changzhou University, Changzhou 213164, P. R. China.

出版信息

Chem Commun (Camb). 2017 Jan 17;53(6):1152-1155. doi: 10.1039/c6cc09154g.

Abstract

A gold-catalyzed sequential annulation reaction to prepare 3,4-fused bicyclic furan compounds has been realized by employing 2-(1-alkynyl)-2-alken-1-ones and 1,3,5-triazines as the starting materials under mild reaction conditions. This protocol features multiple bond formation in a single operation with the incorporation of two nitrogen and two carbon atoms into the final products. A mechanistic investigation reveals that the sequential annulations involved an unprecedented stepwise [3+2+2]-cycloaddition.

摘要

通过使用2-(1-炔基)-2-烯-1-酮和1,3,5-三嗪作为起始原料,在温和的反应条件下实现了金催化的串联环化反应,用于制备3,4-稠合双环呋喃化合物。该方法的特点是在一次操作中形成多个键,并将两个氮原子和两个碳原子引入最终产物中。机理研究表明,串联环化涉及一个前所未有的逐步[3+2+2]环加成反应。

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