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Synthesis of pyrazolo[5,1-a]isoquinolines through copper-catalyzed regioselective bicyclization of N-propargylic sulfonylhydrazones

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Abstract

An expeditious strategy for the synthesis of pyrazolo[5,1-a]isoquinolines has been developed. The tricyclic scaffolds are formed through a four-step cascade sequence, including copper(II)-catalyzed regioselective bicyclization, nucleophilic addition of H2O, aerobic oxidation, and aromatization through eliminating a molecule of TsH. The synthetic utility of this method is demonstrated through the synthesis of a potential CDC25B inhibitor.

Graphical abstract: Synthesis of pyrazolo[5,1-a]isoquinolines through copper-catalyzed regioselective bicyclization of N-propargylic sulfonylhydrazones

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Publication details

The article was received on 30 Mar 2017, accepted on 22 Apr 2017 and first published on 27 Apr 2017


Article type: Research Article
DOI: 10.1039/C7QO00249A
Citation: Org. Chem. Front., 2017, Advance Article
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    Synthesis of pyrazolo[5,1-a]isoquinolines through copper-catalyzed regioselective bicyclization of N-propargylic sulfonylhydrazones

    H. Tang, J. Zeng, J. Chen, Y. Zhou, R. Li and Z. Zhan, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00249A

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