Access to Isoxazoles via Photo-oxygenation of Furan Tethered α-Azidoketones
Photocatalyst-free visible light-enabled direct oxygenation of furan-tethered α-azidoketones was studied. The reaction yielded various products depending on the substituents, with isoxazoles forming as the major products. The findings suggest that singlet oxygen was generated during the reaction and reacted with α-azidoketones in a [4 + 2] fashion to yield endoperoxides, which rearranged in multiple ways to generate isoxazoles. Some of the synthesized isoxazoles were evaluated as α-glucosidase inhibitors, and three of them <b>5bi</b>, <b>5bj</b>, and <b>5bl</b> exhibited good activity with IC<sub>50</sub> values of 454.57 ± 29.34, 147.84 ± 2.28, and 272.58 ± 42.06 μM, respectively, when compared with the standard drug acarbose (IC<sub>50</sub> = 1224.33 ± 126.72 μM).
Authors
- Ram Awatar Maurya (ORCID: https://orcid.org/0000-0003-2431-8614)
- Satheesh Borra (ORCID: https://orcid.org/0000-0002-1766-1708)
- Sabapathi Gokulnath (ORCID: https://orcid.org/0000-0001-9299-5217)
- Prasenjit Manna (ORCID: https://orcid.org/0000-0003-1952-6531)
- Anupriya Borah
- Sylvia Jaya Kumar
- Uma Devi Newar
Institutions
- North East Institute of Science and Technology (IN)
- Korea Research Institute of Chemical Technology (KR)
- Indian Institute of Science Education and Research Thiruvananthapuram (IN)
- Academy of Scientific and Innovative Research (IN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-08-22
- DOI
- https://doi.org/10.1021/acs.joc.4c01312
- Citations
- 3
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.75
Funders
- Department of Science and Technology, Ministry of Science and Technology, India
- Council of Scientific and Industrial Research, India