Solvent-controlled and selective synthesis of mono- and bis-indolyl products in Brønsted acid catalyzed aza-Friedel-Crafts reactions of indoles with cyclic imines

详细信息    查看全文

• 作者：You-Qing Wang ; ^{yqwang@henu.edu.cn" class="auth_mail" title="E-mail the corresponding author} ; Zhong-Shu Wei ; Chao-Qun Zhu ; Yuan-Yuan Ren ; Chunrui Wu ; ^{wyouqing@hotmail.com" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Cyclic imines ; Friedel&ndash ; Crafts reaction ; Indoles ; Nitrogen heterocycles ; Solvent effects
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：4 August 2016
• 年：2016
• 卷：72
• 期：31
• 页码：4643-4654
• 全文大小：1030 K

文摘

Studies to investigate the selectivity and scope of acid-catalyzed aza-Friedel–Crafts reactions of seven-membered cyclic imine dibenzo[b,f][1,4]oxazepines with various indoles have been carried out. In the presence of 10 mol % trifluoroacetic acid (TFA), the selectivity of this reaction can be controlled in different solvents, affording mono-indole substituted products in THF and bis-indole substituted products in DCM as major products. Unsymmetric bis-indole substituted products can be obtained via a sequential procedure. Structurally diverse indole derivatives can be constructed using cyclic imines as the substrates with the reaction featuring: mild conditions, solvent-controlled efficient selectivity, and no need for metals but using easy accessible TFA as a catalyst. Moreover, the potential anti-tumor activity of the new functionalized indole products obtained has been studied by MTT assays.