104722-84-1Relevant academic research and scientific papers
Direct access to α-sulfenylated amides/esters: Via sequential oxidative sulfenylation and C-C bond cleavage of 3-oxobutyric amides/esters
Jiang, Yi,Deng, Jie-Dan,Wang, Hui-Hong,Zou, Jiao-Xia,Wang, Yong-Qiang,Chen, Jin-Hong,Zhu, Long-Qing,Zhang, Hong-Hua,Peng, Xue,Wang, Zhen
supporting information, p. 802 - 805 (2018/02/06)
An efficient, environmentally benign and unprecedented synthesis of various α-sulfenylated amides/esters has been developed under oxygen atmosphere. The reaction shows good functional group tolerance and excellent chemo/regioselectivity. All the desired products were obtained in moderate to excellent yields, even on the gram scale. Practically, the related α-thiol Weinreb amide can be readily transferred to a series of prospective compounds, and selenium atom can be introduced to the α-sites of the amides in high yields.
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.
Fluorinations of α-seleno carboxylic acid derivatives with hypervalent (difluoroiodo)toluene
Arrica, Maria A.,Wirth, Thomas
, p. 395 - 403 (2007/10/03)
A very efficient synthesis of (difluoroiodo)toluene avoiding the use of elemental chlorine and elemental fluorine is described. We have fluorinated a series of α-acceptor substituted selenides using (difluoroiodo)toluene. The reactions are usually very clean and under the reaction conditions no further oxidized products are observed. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
REACTION OF DIAZOMETHANE WITH SELENOESTERS PREPARATION OF α-(ALKYL- OR ARYLSELENO)METHYL KETONES AND METHYL KETONES
Back, Thomas G.,Kerr, Russell G.
, p. 4759 - 4764 (2007/10/02)
The reaction of diazomethane with a series of selenoesters 1 in the presence of CuI, CuSePh or Cu powder produced α-(alkyl- or arylseleno)methyl ketones 2 in yield of 41-65percent.Methyl ketones 3 and bis(arylseleno)methanes 9 or 14 were formed as by-products.The direct conversion of selenoesters to methyl ketones was accomplished in high yield by the usual reaction with diazomethane, followed by workup with HBr solution.The simultaneous copper-catalyzed reactions of selenoesters 1c and 1i with diazomethane resulted in crossover, with the formation of all four possible α-seleno ketones 2b, 2c, 2h and 2i.A non-concerted mechanism involving attack by the diazo compound upon the acyl carbon atom of an activated selenoester with the formation of a tetrahedral intermediate 11 has been suggested.The reaction of the selenothiocarbamate 4 with diazomethane resulted in 1,3-dipolar cycloaddition to afford 5 instead of insertion into the acyl-selenium bond.
