Synthesis and Beckmann rearrangement of novel (Z)-2-organylselanyl ketoximes: promising agents against grapevine anthracnose infection
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.
Insulinomimetic vanadyl-hydroxythiazolethione complexes with VO(S 2O2) coordination mode: The correlation between the activity and Hammett's substituent constant
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
Hartung, Jens,Schwarz, Michaela,Tangirala, Raghuram S.,Curran, Dennis P.
p. 228 - 228
(2017/09/14)
Towards Improved Alkoxyl Radical Precursors - The Synthesis of N-Alkoxy-4-(p-chlorophenyl)thiazole-2(3H)-thiones
4-(p-Chlorophenyl)-3-hydroxythiazol-2(3H)-thione (3) can be prepared in good yields and in useful quantities from p-chloro acetophenone (1). O-Alkylation of the cyclic thiohydroxamic acid 3 via the respective potassium or the tetraethyl ammonium salts affords the esters 4. A slightly modified procedure allows the conversion of the acid 3 to the mixed anhydrides 5. The esters 4 and the anhydrides 5 are colorless to yellowish crystalline compounds which show a good shelf life. Visible light photolysis of the N-alkoxy derivatives 4e-g and reactive hydrogen donors affords substituted tetrahydrofurans 7 or tetrahydropyrans 8 via an alkoxyl radical pathway.
Hartung, Jens,Schwarz, Michaela
p. 848 - 850
(2007/10/03)
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