Synthesis of Isoxazolines and Isoxazoles via Metal-Free Desulfitative Cyclization
作者： Qiu Sun , Ling He , Jiaxin Cheng , Ze Yang , Yuansheng Li
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摘要: A novel, one-pot reaction for the synthesis of isoxazolines and isoxazoles is developed via a cascade process under metal-free conditions. The approach involves formation intramolecular C–N C–O bonds intermolecular C–C from aromatic alkenes or alkynes N-hydroxysulfonamides using hypervalent iodine(VII) iodine as oxidant. Activation C–H bonds/construction bonds/elimination SO2/C–N bond achieved in sequence system.
thieme-connect.de参考文章(13)
Henry Feuer, Nitrile oxides, nitrones, and nitronates in organic synthesis : novel strategies in synthesis Wiley-Interscience. ,(2008)
Xu Zhu, Yi-Feng Wang, Wei Ren, Feng-Lian Zhang, Shunsuke Chiba, TEMPO-mediated aliphatic C-H oxidation with oximes and hydrazones. Organic Letters. ,vol. 15, pp. 3214- 3217 ,(2013) , 10.1021/OL4014969
G. Bianchi, P. Grünanger, Conversion of 2-isoxazolines to isoxazoles Tetrahedron. ,vol. 21, pp. 817- 822 ,(1965) , 10.1016/0040-4020(65)80014-X
Sandeep Bhosale, Santosh Kurhade, Samir Vyas, Venkata P. Palle, Debnath Bhuniya, Magtrieve™ (CrO2) and MnO2 mediated oxidation of aldoximes: studying the reaction course Tetrahedron. ,vol. 66, pp. 9582- 9588 ,(2010) , 10.1016/J.TET.2010.10.029
Shibing Tang, Jinmei He, Yongquan Sun, Liuer He, Xuegong She, Efficient and Regioselective Synthesis of 5-Hydroxy-2-isoxazolines: Versatile Synthons for Isoxazoles, β-Lactams, and γ-Amino Alcohols The Journal of Organic Chemistry. ,vol. 75, pp. 1961- 1966 ,(2010) , 10.1021/JO1000065
Masafumi Ueda, Aoi Sato, Yuki Ikeda, Tetsuya Miyoshi, Takeaki Naito, Okiko Miyata, Direct synthesis of trisubstituted isoxazoles through gold-catalyzed domino reaction of alkynyl oxime ethers. Organic Letters. ,vol. 12, pp. 2594- 2597 ,(2010) , 10.1021/OL100803E
Alan P. Kozikowski, Philip D. Stein, INOC route to carbocyclics: A formal total synthesis of (±)-sarkomycin Journal of the American Chemical Society. ,vol. 104, pp. 4023- 4024 ,(1982) , 10.1021/JA00378A049
Chengliang Li, Hongmei Deng, Chunju Li, Xueshun Jia, Jian Li, Palladium-Catalyzed Synthesis of Δ(2)-Isoxazoline from Toluene Derivatives Enabled by the Triple Role of Silver Nitrate. Organic Letters. ,vol. 17, pp. 5718- 5721 ,(2015) , 10.1021/ACS.ORGLETT.5B03059
Satoshi Minakata, Sota Okumura, Toshiki Nagamachi, Youhei Takeda, Generation of Nitrile Oxides from Oximes Using t-BuOI and Their Cycloaddition Organic Letters. ,vol. 13, pp. 2966- 2969 ,(2011) , 10.1021/OL2010616
W. T. Haskins, Raymond M. Hann, C. S. Hudson, The Structure of Dibenzylidene Dulcitol (1,3:4,6-Dibenzylidene-dulcitol)1 Journal of the American Chemical Society. ,vol. 64, pp. 132- 136 ,(1942) , 10.1021/JA01253A034