The cyclization/rearrangement of α-hydroxy ketones with trifluoromethyl N -acylhydrazones to synthesize multi-substituted trifluoromethyloxazolines
A highly efficient and metal-free [3+2] cyclization/rearrangement reaction toward the synthesis of multisubstituted trifluoromethyloxazolines from α-hydroxyketones and trifluoromethyl N -acylhydrazones has been developed. The unprecedented rearrangement of the amide fragment under acidic conditions...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2023-11, Vol.59 (96), p.14293-14296 |
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| container_issue | 96 |
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| container_title | Chemical communications (Cambridge, England) |
| container_volume | 59 |
| creator | Wang, Junjiao Shang, Yongwei Zhao, Xiujuan Cui, Zhenli Li, Yang Wang, Ke-Hu Huang, Danfeng Hu, Yulai Wang, Na Feng, Lei |
| description | A highly efficient and metal-free [3+2] cyclization/rearrangement reaction toward the synthesis of multisubstituted trifluoromethyloxazolines from α-hydroxyketones and trifluoromethyl
N
-acylhydrazones has been developed. The unprecedented rearrangement of the amide fragment under acidic conditions after cleavage of the N–N bond of acylhydrazones has opened up new avenues for the development of reactions involving trifluoromethyl
N
-acylhydrazones. DFT calculations show that the mechanism involves multiple proton transfer processes. |
| doi_str_mv | 10.1039/d3cc03854h |
| format | Article |
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| fulltext | fulltext |
| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2023-11, Vol.59 (96), p.14293-14296 |
| issn | 1359-7345 1364-548X |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2890362905 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Chemical synthesis Ketones |
| title | The cyclization/rearrangement of α-hydroxy ketones with trifluoromethyl N -acylhydrazones to synthesize multi-substituted trifluoromethyloxazolines |
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