Guangdong Provincial Key Laboratory of New Drug Screening, School of Pharmaceutical Sciences, Southern Medical University, 1838 Guangzhou Avenue North, Baiyun District, Guangzhou 510515, People's Republic of China.
J Org Chem. 2023 Jun 2;88(11):6623-6632. doi: 10.1021/acs.joc.2c02972. Epub 2023 May 11.
Herein, we present a copper-mediated C4-benzylation of 5-aminopyrazoles with 3-indoleacetic acids. Various benzylated 5-aminopyrazoles are prepared in good-to-excellent yields under basic and ligand-free conditions in the presence of copper acetate. Moreover, this benzylation method is applicable to other substrates, including naphthylamine, 2-aminochromen-4-one, and enamines. Some products exhibit antiproliferative activities against cancer cell lines. In addition, the C4-benzylated products are cyclized into 1-pyrazolo[4',3':6,7]azepino[3,4-]indoles with aldehydes via one-pot two-step processes; notably, the cyclized products exhibit fluorescence emissions with large Stokes shifts.
在此，我们提出了一种铜介导的 5-氨基吡唑与 3-吲哚乙酸的 C4-苄基化反应。在醋酸铜存在下，在碱性和无配体条件下，各种苄基化的 5-氨基吡唑以良好至优异的产率得到制备。此外，该苄基化方法适用于其他底物，包括萘胺、2-氨基色酮-4-酮和烯胺。一些产物对癌细胞系表现出抗增殖活性。此外，C4-苄基化产物可与醛通过一锅两步法环化成 1-吡唑并[4',3':6,7]氮杂[3,4-]吲哚；值得注意的是，环化产物表现出具有大斯托克斯位移的荧光发射。
