[3 + 2] Cycloaddition of <i>N</i>-Amino(iso)quinolinium Salts with Vinylsulfonium Salt: Synthesis of Pyrazolo[1,5-<i>a</i>]quinoline and Pyrazolo[5,1-<i>a</i>]isoquinoline Derivatives
In this study, we reported the utilization of vinylsulfonium salt as a highly efficient dipolarophile, leveraging the facile leaving ability of its sulfide moiety, to engage in a [3 + 2] cycloaddition with <i>N</i>-amino(iso)quinolinium salts. This approach facilitates the construction of various C<sub>1</sub>/C<sub>2</sub>-unsubstituted pyrazolo(iso)quinoline skeletons. The transformation is conducted under catalyst- and external oxidant-free conditions. Furthermore, the extended gram-scale reaction demonstrates the practical applicability of the developed protocol.
Authors
- Hui Wu (ORCID: https://orcid.org/0000-0003-0296-5204)
- Qingmei Ge (ORCID: https://orcid.org/0000-0002-4918-4176)
- Wenfeng Zhao (ORCID: https://orcid.org/0009-0007-2093-6892)
- Hang Cong (ORCID: https://orcid.org/0000-0001-6855-5123)
- Mao Liu (ORCID: https://orcid.org/0000-0002-2935-1117)
- Nan Jiang (ORCID: https://orcid.org/0000-0002-3446-890X)
Institutions
- Guizhou University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-05-16
- DOI
- https://doi.org/10.1021/acs.joc.5c00377
- Primary Topic
- Synthesis and Biological Evaluation
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- Guizhou Science and Technology Department
- Natural Science Foundation of Guizhou Province
- Department of Education of Guizhou Province