14181-73-8Relevant academic research and scientific papers
An Intramolecular Wittig Approach toward Heteroarenes: Synthesis of Pyrazoles, Isoxazoles, and Chromenone-oximes
Khairnar, Pankaj V.,Lung, Tsai-Hui,Lin, Yi-Jung,Wu, Chi-Yi,Koppolu, Srinivasa Rao,Edukondalu, Athukuri,Karanam, Praneeth,Lin, Wenwei
supporting information, p. 4219 - 4223 (2019/06/17)
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.
An efficient synthesis of 2-isoxazolines from α-haloketone oximes and dimethyl sulfonium salts
Zhao, Sen,Wang, Hang,Sun, Shaofa,Guo, Haibing,Chen, Zhiyu,Wang, Jian,Wang, Lu,Liang, Steven,Wang, Gangqiang
supporting information, p. 382 - 385 (2019/01/04)
2-Isoxazolines were synthesized efficiently from a formal [4+1] cycloaddition of nitrosoalkenes and sulfur ylides, which were generated in situ from α-haloketone oximes and dimethyl sulfonium salts. This approach provides a new method to synthesize a rang
Synthesis and Beckmann rearrangement of novel (Z)-2-organylselanyl ketoximes: promising agents against grapevine anthracnose infection
Waskow, Bianca,Mano, Renata A.,Giacomini, Rafaela X.,Oliveira, Daniela H.,Schumacher, Ricardo F.,Wilhelm, Ethel A.,Luchese, Cristiane,Savegnago, Lucielli,Jacob, Raquel G.
supporting information, p. 5575 - 5580 (2016/11/25)
We present here the synthesis of novel (Z)-2-organylselanyl ketoximes by nucleophilic substitution reaction of E/Z mixtures of 2-bromo ketoximes with nucleophilic species of selenium, which were generated in situ by simple cleavage of diorganyl diselenides with NaBH4using ethanol/THF as solvent. The new 2-organylselanyl ketoximes were synthesized in moderate to good yields and with selectivity for the (Z)-configuration. The synthesized (Z)-2-arylselanylacetophenone oximes were submitted to the Beckmann rearrangement, furnishing the corresponding N-aryl-2-(selanyl)acetamides. (Z)-1-Phenyl-2-(phenylselanyl) ketoxime has antifungal activity against Sphaceloma ampelinum and a good level of antioxidant activity in vitro in DPPH, ABTS, FRAP and lipid peroxidation assays.
Hetero-Diels-Alder reaction of [60]fullerene with nitrosoalkene
Yang, Hai-tao,Ruan, Xiao-Jiao,Miao, Chun-bao,Xi, Hai-tao,Jiang, Yan,Meng, Qi,Sun, Xiao-qiang
body text, p. 7337 - 7339 (2010/03/01)
A new type of stable C60-fused dihydrooxazine derivatives was successfully prepared by the hetero-Diels-Alder reaction of C60 with nitrosoalkene generated in situ by extrusion of HBr from the corresponding α-bromooxime.
Insulinomimetic vanadyl-hydroxythiazolethione complexes with VO(S 2O2) coordination mode: The correlation between the activity and Hammett's substituent constant
Katoh, Akira,Yamaguchi, Mika,Saito, Ryota,Adachi, Yusuke,Sakurai, Hiromu
, p. 1274 - 1275 (2007/10/03)
Four kinds of vanadyl-hydroxythiazolethione complexes with VO(S 2O2) coordination mode were newly synthesized, and demonstrated for the first time that the insulinomimetic activity apparently correlates to the Hammett's substituent c
The Cycloaddition of α-Nitrosostyrenes to Olefins. Investigations of the Scope and Mechanism of the Reaction
Davies, David E.,Gilchrist, Thomas L.,Roberts, Tony G.
, p. 1275 - 1282 (2007/10/02)
Cycloaddition of α-nitrosostyrene (1a) to several substituted styrenes is shown to give 3-phenyl-5,6-dihydro-4H-1,2-oxazines (2) in moderate yield.Reactions with 4-nitro-α-nitrosostyrene (1b) give better yields of the corresponding adducts (3).The preferred conformations of the adducts are deduced from their n.m.r. spectra.The observed regio- and stereo-selectivities of the addition are interpreted in terms of one-step addition in which the olefins act as the donor components.The first example of a formal 1,3-dipolar addition of a vinyl nitroso compound is provided by the formation of the nitrone (5) as a minor product of the reaction of α-nitrosostyrene with 2-methoxypropene.The relative yield of this nitrone is not increased by the change to a more polar solvent, nor by the use of α-bromoacetophenone anti-oxime in place of the usual syn-isomer as the precursor of α-nitrosostyrene.It is suggested that this, and other minor products (4) isolated from the cycloadditions, may be formed because of steric inhibition of the usual Diels-Alder-type process.
