Ma Yong-Gang, Huang Meng-Qiao, Liu Zhenhua, Liu Jian-Quan, Wang Xiang-Shan
School of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthesis for Functional Materials , Jiangsu Normal University , Xuzhou Jiangsu 221116 , P. R. China.
College of Chemistry, Chemical Engineering and Materials Science , Shandong Normal University , Jinan 250014 , P. R. China.
J Org Chem. 2018 Aug 17;83(16):9504-9509. doi: 10.1021/acs.joc.8b01180. Epub 2018 Jul 13.
A series of ( E)- N-aryl-4 H-thiochromen-4-imines has been conveniently obtained through a cascade reaction between o-bromobenzothioamides and terminal alkynes. This novel approach probably involved an initial generation of benzothietane-2-imine intermidates via an intramolecular Ullmann reaction under CuI/L-proline cocatalysis and alkaline conditions followed by imine alkynylation, ring opening, and cyclization sequences to provide the unexpected 4 H-thiochromen-4-imines rather than isothiochromans.
通过邻溴苯硫代酰胺与末端炔烃之间的串联反应，简便地获得了一系列（E）-N-芳基-4H-硫代色烯-4-亚胺。这种新方法可能首先是在碘化亚铜/ L-脯氨酸共催化和碱性条件下，通过分子内乌尔曼反应生成苯并硫杂环丁烷-2-亚胺中间体，随后经过亚胺炔基化、开环和环化序列，得到了意想不到的4H-硫代色烯-4-亚胺，而不是异硫代色满。
