Citation: Zhaoquan Guo, Wenyao Ding, Zhenguo Xi, Lin Yang, Gang Lu, Hongyin Gao. Protecting-group-dependent chemo- and regioselective cascade rearrangement of N-arylhydroxylamines with N-thiophthalimides[J]. Chinese Chemical Letters, ;2026, 37(2): 111196. doi: 10.1016/j.cclet.2025.111196 shu

Protecting-group-dependent chemo- and regioselective cascade rearrangement of N-arylhydroxylamines with N-thiophthalimides

School of Chemistry and Chemical Engineering, Shandong University, Ji′nan 250100, China

ganglu@sdu.edu.cn

hygao@sdu.edu.cn

Received Date: 3 January 2025
Revised Date: 27 March 2025
Accepted Date: 10 April 2025
Available Online: 12 April 2025

Figures(8)

Sulfoxides and sulfide compounds have broad-spectrum biological properties and have received considerable attention in the past few decades. Herein we reported two metal and oxidant-free, practical and efficient methods for the synthesis of highly synthetically useful and structurally diverse ortho-aminoaryl sulfoxides and 3,4,5-trisubstituted oxazolones from readily accessible N-arylhydroxylamines and N-thiophthalimides. This rapid transformation occurred smoothly to achieve chemo- and regioselective cascade rearrangements due to the differences of the protecting-groups of the nitrogen atom of N-arylhydroxyamines. DFT studies suggested that the competing S-O and S-C bond formations via S_N2 nucleophilic substitution are crucial for the observed protecting-group-dependent chemoselectivity. Subsequent applications have shown that these two protocols might be powerful tools for the construction of sulfur-containing complex molecules under simple conditions.
- Arylhydroxylamines,
- N-Thiophthalimides,
- Regioselectivity,
- [2,3]-Sigmatropic rearrangement,
- Oxazolones
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沈阳化工大学材料科学与工程学院沈阳 110142