通过碱介导的Ugi反应后Conia-ene环化快速合成C2-季碳3-亚甲基吲哚啉

Rapid access to C2-quaternary 3-methyleneindolines base-mediated post-Ugi Conia-ene cyclization.

作者信息

Zhao Shuang, He Yi, Gao Feiyu, Wei Yue, Zhang Jiawei, Chen Mengxiao, Gao Yunyun, Zhang Yuan, Liu Jun-Yan, Guo Zufeng, Li Zhenghua, Nie Shenyou

机构信息

Center for Novel Target and Therapeutic Intervention, Institute of Life Sciences, Chongqing Medical University, Chongqing 400016, China.

School of Science, Westlake University, Zhejiang 310030, China.

出版信息

Chem Commun (Camb). 2023 Mar 9;59(21):3099-3102. doi: 10.1039/d2cc06281j.

DOI:10.1039/d2cc06281j

PMID:36804590

Abstract

Highly efficient synthesis of diverse 2,2-disubstituted 3-methyleneindoline derivatives through a one-pot base-promoted post-Ugi 5--dig "Conia-ene"-type cyclization has been disclosed. The mechanism study indicates that an intramolecular hydrogen bond may play a vital role in this process. The antiproliferative evaluation of cancer cell lines reveals that this protocol provides practical use in the green synthesis of bioactive compound libraries.

摘要

通过一锅碱促进的Ugi反应后5-重氮-“Conia-ene”型环化反应高效合成多种2,2-二取代3-亚甲基吲哚啉衍生物的方法已被公开。机理研究表明，分子内氢键可能在该过程中起关键作用。对癌细胞系的抗增殖评估表明，该方法在生物活性化合物库的绿色合成中具有实际应用价值。