HCl/DMSO/HFIP-Mediated Chlorination of Pyrrolo2,1-aisoquinolines and Other Electron-Rich Heteroarenes

An efficient oxidative chlorination of pyrrolo[2,1-a]isoquinolines has been established using HCl (aq) as the chlorine source and DMSO as the terminal oxidant in HFIP at ambient temperature. A variety of chlorinated pyrrolo[2,1-a]isoquinoline derivatives have been prepared readily in 23 to 99% yield...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-07, Vol.89 (14), p.9789
Main Authors: Zhou, Jing, Huang, Xiang, Yu, Xin, Yang, Liu, Han, Jia-Yi, Lhazom, Tsesong, Cui, Hai-Lei
Format: Article
Language:English
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Summary:An efficient oxidative chlorination of pyrrolo[2,1-a]isoquinolines has been established using HCl (aq) as the chlorine source and DMSO as the terminal oxidant in HFIP at ambient temperature. A variety of chlorinated pyrrolo[2,1-a]isoquinoline derivatives have been prepared readily in 23 to 99% yields. This chlorination strategy can be expanded to the functionalization of other electron-rich heteroarenes including substituted pyrroles, indoles, and naphthols.An efficient oxidative chlorination of pyrrolo[2,1-a]isoquinolines has been established using HCl (aq) as the chlorine source and DMSO as the terminal oxidant in HFIP at ambient temperature. A variety of chlorinated pyrrolo[2,1-a]isoquinoline derivatives have been prepared readily in 23 to 99% yields. This chlorination strategy can be expanded to the functionalization of other electron-rich heteroarenes including substituted pyrroles, indoles, and naphthols.
ISSN:1520-6904
1520-6904
DOI:10.1021/acs.joc.4c00151