一锅法通过顺序去芳构化和 Ag 催化环化/CsCO 介导的加成/芳构化反应合成 4-(咪唑-1-基)吲哚衍生物。

One-pot synthesis of 4-(imidazol-1-yl)indole derivatives through a sequential dearomatization and Ag-catalyzed cyclization/CsCO-mediated addition/aromatization reaction.

机构信息

Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, People's Republic of China.

School of Chemistry and Chemical Engineering, Shandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell Technology, Liaocheng University, Liaocheng 252059, Shandong, People's Republic of China.

出版信息

Org Biomol Chem. 2023 May 24;21(20):4245-4256. doi: 10.1039/d3ob00316g.

DOI:10.1039/d3ob00316g

PMID:37145103

Abstract

A convenient one-pot assembly of 4-(imidazol-1-yl)indole derivatives from easily accessible -alkynylanilines and imidazoles has been developed. The sequential dearomatization and Ag(I)-catalyzed cyclization/CsCO-mediated conjugate addition/aromatization cascade reactions exhibit high efficiency and excellent selectivity. The combined use of a silver(I) salt and cesium carbonate is significant for facilitating this domino transformation. The 4-(imidazol-1-yl)indole products could be easily converted to the corresponding derivatives and might be valuable in biological chemistry and medicinal science.

摘要

已开发出一种从易得的 - 炔基苯胺和咪唑出发方便的一锅法合成 4-(咪唑-1-基)吲哚衍生物的方法。顺序去芳构化和 Ag(I)-催化环化/CsCO 介导的共轭加成/芳构化级联反应具有高效率和优异的选择性。银（I）盐和碳酸铯的联合使用对于促进这种多步转化非常重要。4-(咪唑-1-基)吲哚产物可以很容易地转化为相应的衍生物，在生物化学和药物科学中可能具有重要价值。