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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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
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container_issue 14
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container_title Journal of organic chemistry
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Huang, Xiang
Yu, Xin
Yang, Liu
Han, Jia-Yi
Lhazom, Tsesong
Cui, Hai-Lei
description 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.
doi_str_mv 10.1021/acs.joc.4c00151
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title HCl/DMSO/HFIP-Mediated Chlorination of Pyrrolo2,1-aisoquinolines and Other Electron-Rich Heteroarenes
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