期刊
ORGANIC CHEMISTRY FRONTIERS
卷 9, 期 10, 页码 2779-2785出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo00401a
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资金
- Guangdong Major Project of Basic and Applied Research [2019B030302009]
- Guangdong Provincial Key Laboratory of Catalysis [2020B121201002]
- Science, Technology and Innovation Commission of Shenzhen Municipality [JCYJ20180508162429786]
- Southern University of Science and Technology
A synthetic method for constructing trifluoromethyl-pyrrolo[2,1-a]isoquinolines via decarboxylation and photocatalytic reactions is described. This method exhibits broad substrate compatibility and enables facile access to pharmaceutically active derivatives.
The pyrrolo[2,1-a]isoquinoline core structure is prevalent in marine natural products and its fluorinated derivatives are potential medicinal compounds. Herein is described a tungsten-catalysed decarboxylative [3 + 2] cycloaddition aromatization process that could be used to construct trifluoromethyl-pyrrolo[2,1-a]isoquinolines. This photocatalytic reaction tolerates a panel of functional groups including ester, nitrile, ketone and alkene (24 examples, up to 94% yield). The pharmaceutically useful trifluoromethyl substituted lamellarin derivatives and late-stage derivatization of drugs are facilely accessible via the current synthetic approach.
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