文献类型：期刊文献

英文题名：Cu-Catalyzed Cascade Annulation of Alkynols with 2-Azidobenzaldehydes: Access to 6H-Isochromeno[4,3-c]quinoline

作者：Mao, Xiao-Feng;Zhu, Xiao-Ping;Li, Deng-Yuan;Liu, Pei-Nian[1]

机构：[1]East China Univ Sci & Technol, Shanghai Key Lab Funct Mat Chem, Key Lab Adv Mat, Meilong Rd 130, Shanghai 200237, Peoples R China; East China Univ Sci & Technol, Sch Chem & Mol Engn, Meilong Rd 130, Shanghai 200237, Peoples R China

年份：2017

卷号：82

期号：13

起止页码：7032

外文期刊名：JOURNAL OF ORGANIC CHEMISTRY

收录：;EI(收录号：20172803941980);WOS:【SCI-EXPANDED(收录号:WOS:000405358000057)，CCR-EXPANDED(收录号:WOS:000405358000057)】；

基金：This work was supported by the National Natural Science Foundation of China (project nos. 21372072, 21421004, 21561162003, and 21672059), the Program for Eastern Scholar Distinguished Professor, the Fundamental Research Funds for the Central Universities, and the Program of Introducing Talents of Discipline to Universities (B16017).

语种：英文

外文关键词：Cyclization

摘要：A copper-catalyzed cascade reaction of alkynols and 2-azidobenzaldehydes has been achieved, giving 6H-isochromeno [4,3-c] quinoline in yields of 40-81%. This reaction provides a novel, concise strategy for rapidly constructing compounds with fused N- and O-containing heterocycles. In contrast to previously reported reactions of alkynols in which the first step is intramolecular cycloisomerization, the first step in this novel reaction of alkynols is entropically unfavorable intermolecular addition. The resulting hemiacetal intermediate then undergoes intramolecular cyclization and aromatization to afford the product.