Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 20, Issue 40, Pages 7896-7899Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ob01546c
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Funding
- JSPS KAKENHI [JP17H01523]
- Research Support Project for Life Science and Drug Discovery (Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)) from the Japan Agency for Medical Research and Development (AMED) [JP22ama121044]
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In this study, photoirradiation of alpha-(2-nitrophenyl)ketones resulted in the production of cyclic hydroxamates. The reaction involved photoinduced oxygen transfer from the nitro group to the benzylic position, leading to the formation of an alpha-hydroxyketone with a nitroso group. Subsequent addition of the nitroso group to the ketone moiety and the cleavage of the C-C sigma bond between the carbonyl group and the benzyl position produced hydroxamic acid, which then underwent hemiacetal formation to yield cyclic hydroxamate.
Photoirradiation of alpha-(2-nitrophenyl)ketones produced cyclic hydroxamates. The reaction proceeded via photoinduced oxygen transfer from the nitro group to the benzylic position, forming an alpha-hydroxyketone having a nitroso group. Subsequent addition of the nitroso group to the ketone moiety and the concomitant cleavage of the C-C sigma bond between the carbonyl group and the benzyl position produced hydroxamic acid, which underwent formation of a hemiacetal to give cyclic hydroxamate.
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