- 3, 5-disubstituted isoxazole derivative and synthesis method thereof
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The invention provides a 3, 5-disubstituted isoxazole derivative and a synthesis method thereof, and belongs to the technical field of organic synthesis medicines and medical intermediates. The method comprises the following steps: adding a proper solvent
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Paragraph 0011; 0023; 0031
(2021/08/14)
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- A palladium-catalyzed oxidative aminocarbonylation reaction of alkynone: O -methyloximes with amines and CO in PEG-400
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A palladium-catalyzed oxidative aminocarbonylation of O-methyloximes and amines under aerobic conditions with PEG-400 as an environmentally benign medium was accomplished. This novel protocol provides the first straightforward synthetic method for the assembly of structurally diverse 4-carboxamide isoxazoles with high atom- and step-economy and exceptional functional group tolerance. Notably, the employment of ionic liquids as an additive, with air as the sole oxidant, without ligands is an attractive feature of the present approach.
- Li, Jianxiao,Yu, Junsheng,Xiong, Wenfang,Tang, Hao,Hu, Miao,Wu, Wanqing,Jiang, Huanfeng
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supporting information
p. 465 - 470
(2020/02/13)
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- An Intramolecular Wittig Approach toward Heteroarenes: Synthesis of Pyrazoles, Isoxazoles, and Chromenone-oximes
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α-Halohydrazones/ketoximes are transformed into trisubstituted pyrazoles/disubstituted isoxazoles by treatment with phosphine, acyl chloride, and a base. Mechanistic investigations revealed the in situ formation of azo/nitroso olefin intermediates which underwent a tandem phospha-Michael/N- or O-acylation/intramolecular Wittig reaction to afford the heteroarenes in moderate to good yields. Further, proper functionalization of α-haloketoximes and a change of conditions allowed the chemoselective synthesis of chromenone-oximes as well as rearranged isoxazoles, thereby realizing a diversity-oriented synthesis.
- Khairnar, Pankaj V.,Lung, Tsai-Hui,Lin, Yi-Jung,Wu, Chi-Yi,Koppolu, Srinivasa Rao,Edukondalu, Athukuri,Karanam, Praneeth,Lin, Wenwei
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supporting information
p. 4219 - 4223
(2019/06/17)
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- Complementary regioselective synthesis of 3,5-disubstituted isoxazoles from ynones
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Two regioselective synthetic routes towards 3,5-disubstituted isoxazoles from ynones are reported. One route takes place via first converting the ynones to ynone O-methyl oximes, followed by a palladium-catalyzed intramolecular cyclization. The other invo
- Liu, Xiaochen,Hong, Dongsub,She, Zhigang,Hersh, William H.,Yoo, Barney,Chen, Yu
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p. 6593 - 6606
(2018/10/05)
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- Synthesis of 3,5-diarylisoxazoles under solvent-free conditions using iodobenzene diacetate
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A simple and efficient method has been developed for conversion of chalcone oximes to 3,5-diaryl isoxazoles in excellent yields under solvent-free conditions. The synthesized compounds were characterized by infrared spectroscopy, 1H NMR, 13C NMR and HRMS.
- Chandra Sekhar, Kondapalli Venkata Gowri,Sasank, Thripuraribhatla Venkata Naga Varuna Tara,Nagesh, Hunsur Nagendra,Suresh, Narva,Naidu, Kalaga Mahalakshmi,Suresh, Amaroju
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p. 1045 - 1048
(2014/01/06)
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- Efficient and regioselective one-pot synthesis of 3-substituted and 3,5-disubstituted isoxazoles
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(Figure Presented) A series of 3-substituted and 3,5-disubstituted isoxazoles have been efficiently synthesized in moderate to excellent yields by the reaction of N-hydroxyl-4-toluenesulfonamide with α,β-unsaturated aldehydes/ketones. This novel strategy is associated with readily available starting materials, mild conditions, high regioselectivity, and wide scope.
- Tang, Shibing,He, Jinmei,Sun, Yongquan,He, Liuer,She, Xuegong
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supporting information; experimental part
p. 3982 - 3985
(2009/12/03)
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- On the Oximation of Diaryl-β-diketones
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The reaction of asymmetrically substituted β-diketones with hydroxylamine to give 3,5-diarylisoxazoles has been re-investigated, and has been found to occur with a low degree of site-selectivity unless steric effects are operating.The isoxazole that has t
- Bandiera, T.,Gruenanger, P.,Albini, F. Marinone
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p. 1423 - 1428
(2007/10/02)
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- SYNTHESIS AND PROPERTIES OF AZOLES AND THEIR DERIVATIVES. PART XX. STUDIES ON THE THERMOLYSIS OF REGIO AND STEREOISOMERIC DIARYLNITRO-Δ2-ISOXAZOLINES
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Thermolysis of stereoisomeric 3,5-diaryl-4-nitro-Δ2-isoxazolines 1, 3, depending on the applied solvent, leads to 3,5-diarylisoxazoles 4 or mixtures of 3,5-diarylisoxazoles 4 and 3,5-diaryl-4-nitroisoxazoles 6.Under similar conditions, 3,4-diar
- Baranski, Andrzej,Cholewka, Elzbieta
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p. 483 - 494
(2007/10/02)
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- BENZO-γ-PYRONES. PART VIII. REACTION OF CHALCONE DIBROMIDES AND β-DIKETONES WITH HYDROXYLAMINE
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In the reaction of some chalcone dibromides and unsymmetrically substituted diaroylmethanes with hydroxylamine formation of mixture of isomeric isoxazoles was observed and the percentage content of each isomer was established.A new mechanism is proposed for the reaction of β-diketones with hydroxylamine, based on enolic form in accordance with expected substituents effect.
- Maib, Piotr,Basinski, Wlodzimierz,Jerzmanowska, Zofia
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p. 949 - 956
(2007/10/02)
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