- Polymer-supported vinyl sulfone as an efficient reagent for the synthesis of 3-monosubstituted isoxazoles
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Polystyrene-supported vinyl sulfone reagent has been developed and used for solid-phase organic synthesis of 3-monosubstituted isoxazoles by 1,3-dipolar cycloaddition reaction with nitrile oxides and subsequent cleavage from the polymer support through an
- Wu, Guo-Jian,Sheng, Shou-Ri,Li, Dan,Xu, Li-Fan,Huang, Zhen-Zhong
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p. 3034 - 3043
(2013/09/12)
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- Efficient and regioselective synthesis of 5-hydroxy-2-isoxazolines: Versatile synthons for isoxazoles, β-lactams, and γ-amino alcohols
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"Chemical Equation Presented" An efficient and highly regioselective protocol was developed for the preparation of 5-hydroxy2-isoxazolines, which have been proved to be versatile synthons for isoxazles, β-hydroxy oximes, and γ-amino alcohols. β-Lactams, commonly embedded in the skeletons of bioactive natural products, were also synthesized in two steps from β-hydroxy oximes, providing a new strategy for the synthesis of this kind of compounds.
- Tang, Shibing,He, Jinmei,Sun, Yongquan,He, Liuer,She, Xuegong
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scheme or table
p. 1961 - 1966
(2010/06/20)
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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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- Traceless solid-phase synthesis of 3-substituted isoxazoles and 3-substituted 5-iodoisoxazolines using polystyrene-supported vinyl selenide
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A novel facile procedure for the traceless solid-phase synthesis of 3-substituted isoxazoles and 3-substituted 5-iodoisoxazolines in good yields and with excellent purities using polymer-supported vinyl selenide is described. The polymeric reagent can be
- Sheng, Shou-Ri,Xin, Qin,Liu, Xiao-Ling,Sun, Wu-Kang,Guo, Rui,Huang, Xian
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p. 2293 - 2296
(2008/02/02)
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- Substituent effects on 15N and 13C NMR chemical shifts of 3-phenylisoxazoles: A theoretical and spectroscopic study
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The synthesis and assignment of 15N and 13C NMR signals of the isoxazole ring in a series of parasubstituted 3-phenyl derivatives are reported. DFT calculations of 15N and 13C chemical shifts are presented and c
- Schofield, Mark H.,Sorel, Marie-Adele,Manalansan, Ryan J.,Richardson, David P.,Markgraf, J. Hodge
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p. 851 - 855
(2007/10/03)
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- ANTIBACTERIAL 1, 3- OXAZOLIDIN -2- ONE DERIVATIVES
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Compounds of the formula (I), or a pharmaceutically-acceptable salts, or in-vivo-hydrolysable esters thereof, wherein: N-HET is for example triazolyl substituted with R1; R1 is for example optionally substituted (1-4C)alkyl; Q is for
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- One-Pot Synthesis of 3-Substituted Isoxazoles from Phenyl Vinylic Selenide
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Phenyl vinylic selenide was adopted for 1,3-dipolar cycloaddition to nitrile oxides and subsequent oxidation-elimination furnished 3-substituted isoxazoles with good yields in a one-pot, two-step transformation.
- Sheng, Shou-Ri,Liu, Xiao-Ling,Xu, Qu,Song, Cai-Sheng
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p. 2763 - 2764
(2007/10/03)
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- SYNTHESIS OF 3-ARYL-4,5-DIHYDRO-5-HYDROXY-1,2-OXAZOLES BY REACTION OF SUBSTITUTED BENZONITRILE OXIDES WITH THE ENOLATE ION OF ACETALDEHYDE.
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By reaction of substituted benzonitrile oxides with the enolate ion of acetaldehyde (quantitatively generated by the known cycloreversion of THF in the presence of n-butyllithium) a number of 3-aryl-4,5-dihydro-5-hydroxy-1,2-oxazoles (previously unknown or, in two cases, only synthesized by different procedures) have been isolated in high yields.Treatment of such hydroxy-isoxalines with some common bases allows their conversion in high yields into the corresponding isoxazoles.
- Di Nunno, L.,Scilimati, A.
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p. 2181 - 2190
(2007/10/02)
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- SITE SELECTIVITY IN THE REACTIONS OF 1,3-DIPOLES WITH NORBORNADIENE DERIVATIVES
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The cycloadditions of arylazides, benzonitrile oxides and diphenylnitrile imine to norbornadiene derivatives 1a-c showed varying degree of site- and stereo-selectivity.With dipolarophile 1a arylazides and benzonitrile oxides attack, preferentially, the electron-poor tetrasubstituted double bond, while in the case of 1b and 1c is the substituted double bond which enters the cycloaddition.By contrast, 2-diazopropane and C-phenyl-N-methylnitrone react with the sole tetrasubstituted double bond of 1a-c in stereo- and site-specific cycloadditions.The quantitative evaluation of the two possible reaction paths was performed by glc analysis.The compounds detected were those arising from Diels-Alder cycloreversions of the thermally labile intermediate adducts 2 and 3 (Scheme 1).The results were rationalized on the basis of a qualitative perturbation treatment which considers frontier orbital interactions only.
- Cristina, D.,Amici, M. De,Micheli, C. De,Gandolfi, R.
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p. 1349 - 1357
(2007/10/02)
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- 4,5-DIHYDROISOXAZOLES. IV. 4- AND 5-PHENYLTHIO-4,5-DIHYDROISOXAZOLES AND THEIR BEHAVIOUR WITH PERFORMIC ACID
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Several cis- and trans-4,5-dihydroisoxazole derivatives bearing a phenylthio group on C(4) or C(5) have been prepared by cyclo-addition of the corresponding unsaturated sulphides and nitrile oxides.The cyclo-adducts have been oxidized by HCOOH/H2O2.It has been shown that this oxidation leads mainly to isoxazole derivatives (i.e. is accompanied by elimination) when the sulphur-containing substituent is bound to C(5).The 4-phenylthio-substituted regioisomers gave in most cases the corresponding sulphones.
- Bianchetti, Giuseppe,Pocar, Donato,Torricelli, Clara,Arlandini, Emanuele,Gioia, Bruno
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p. 315 - 324
(2007/10/02)
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