Synthesis and Beckmann rearrangement of novel (Z)-2-organylselanyl ketoximes: promising agents against grapevine anthracnose infection

Autor:	Bianca Waskow, Rafaela Xavier Giacomini, Daniela H. de Oliveira, Cristiane Luchese, Ethel A. Wilhelm, Renata A. Mano, Lucielli Savegnago, Ricardo F. Schumacher, Raquel G. Jacob
Rok vydání:	2016
Předmět:	Ethanol ABTS 010405 organic chemistry Chemistry DPPH Organic Chemistry 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Solvent chemistry.chemical_compound Nucleophile Drug Discovery Beckmann rearrangement Nucleophilic substitution Organic chemistry Selectivity
Zdroj:	Tetrahedron Letters. 57:5575-5580
ISSN:	0040-4039
Popis:	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 NaBH4 using 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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::6a64baf0fd7ef69b627b730c565807ce https://doi.org/10.1016/j.tetlet.2016.10.078 Zobrazit plný text záznamu Full Text from ScienceDirect