Construction of Isochromanones via Hemin-Catalyzed Phenol-Enamine Oxidative Annulation
We have developed a hemin-catalyzed biomimetic oxidative annulation of 2,3-dihydroxybenzoic acid with an array of cyclic enamines to form isochromanones in good to excellent yields and high regioselectivity. This formal [4+2] cycloaddition protocol showed high efficiency and remarkable functional group tolerance. Mechanistic studies indicate the involvement of a single-electron oxidation pathway. Preliminary biological investigations showed that isochromanones <b>3ag</b> and <b>3ca</b> exhibited antineoplastic activities against MCF-7 cell lines with IC<sub>50</sub> values of 25.21 and 29.09 μM, respectively.
Authors
- Xinye Bao
- Hongbin Zhai (ORCID: https://orcid.org/0000-0003-2198-1357)
- Tie Wang (ORCID: https://orcid.org/0000-0001-5965-6520)
- Hui Guo (ORCID: https://orcid.org/0000-0002-2054-3876)
- Muhammad Adnan Bashir (ORCID: https://orcid.org/0000-0001-8029-9409)
- Jianguo Sun (ORCID: https://orcid.org/0000-0002-2222-2478)
- Haijun Zhang (ORCID: https://orcid.org/0000-0002-9198-8098)
Institutions
- Sun Yat-sen University (CN)
- Peking University (CN)
- Fifth Affiliated Hospital of Sun Yat-sen University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-11-26
- DOI
- https://doi.org/10.1021/acs.joc.4c01858
- Citations
- 2
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.50
Funders
- Science and Technology Foundation of Shenzhen City
- National Natural Science Foundation of China
- Science, Technology and Innovation Commission of Shenzhen Municipality
- Shenzhen Fundamental Research Program
- Shenzhen-Hong Kong Institute of Brain Science
- Science and Technology Planning Project of Guangdong Province
- National Ten Thousand Talent Program
- Basic and Applied Basic Research Foundation of Guangdong Province