- Aza-Oxyallyl Cation Driven 3-Amido Oxetane Rearrangement to 2-Oxazolines: Access to Oxazoline Amide Ethers
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Herein, we report a highly facile and unprecedented activation of 3-amido oxetanes to synthesize 2-oxazoline amide ethers using a transient electrophilic aza-oxyallyl cation as an activating as well as an alkylating agent under mild reaction conditions. The aza-oxyallyl cation driven intramolecular rearrangement of 3-amido oxetanes to 2-oxazolines is the hallmark of this transformation and is a new addition to the reactivity profile of aza-oxyallyl cations.
- Banerjee, Prabal,Saha, Debarshi,Taily, Irshad Maajid
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- Efficient synthesis and antibacterial evaluation of (±)-Yanglingmycin and its analogues
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An efficient synthetic route was developed for the large-scale preparation of (±)-Yanglingmycin and its analogues. Three series of derivatives of (±)-Yanglingmycin were synthesized and the structures of all compounds were elucidated by analyses of NMR and ESI-MS spectra data. Moreover, their antibacterial activities against seven species of bacteria were systematically evaluated by the micro-broth dilution method, most of which displayed considerable activity. It was worth noting that compounds 5b, 5c, 5d, 6g, and 7 were found to be the most promising leading candidates, with peak MIC values of 0.98 μg.mL-1 for Bacillus subtilis, which is superior to positive controls (MIC = 3.91 μg.mL-1). The above results might lay the firm foundation for the design and synthesis of novel antibacterial drugs based on (±)-Yanglingmycin.
- Dan, Wenjia,Geng, Huiling,Qiao, Jianwen,Guo, Rui,Wei, Shaopeng,Li, Longbo,Wu, Wenjun,Zhang, Jiwen
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- Stereoselective Cycloaddition of Nitrile Oxides to 4-Vinyl-Oxazolines and -Oxazolidines
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Cycloaddition of nitrile oxides to 4-vinyl-2-oxazoline 1 and to 4-vinyloxazolidine 2 afford diastereomeric mixtures of 2-isoxazolines in which the erythro product predominates (32-64percent d.e.).In contrast, the corresponding reactions with acyclic analogue 3 favoured the threo-adducts and were less selective (8-20percent d.e.).Key Words: 1,3-dipolar cycloaddition; nitrile oxides; isoxazolines
- Boyd, Ewan C.,Paton, R. Michael
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p. 3169 - 3172
(2007/10/02)
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