Toward pyridine-fused selenium-containing antioxidants.
Photolysis of the thiohydroximate ester derivative 21 of 2-carboethoxy-2-(2- (benzylseleno)pyridin-3-yl)tridecylcarboxylic acid (20) affords 2-dodecyl-2- carboethoxy-2,3-dihydroselenolo[2,3-b]pyridine (22) in 89% yield in a process presumably involving intramolecular homolytic substitution by a tertiary alkyl radical at selenium with loss of a benzyl radical. Work toward extending this methodology to the preparation of pyridine-fused selenium analogues of antioxidants is described.
Fenner
Tahli
T
School of Chemistry, Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria, Australia.
Schiesser
Carl H
CH
D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000138:chemical synthesis / Q000737:chemistry; D010782:Photolysis; D011725:Pyridines / Q000737:chemistry*; D017382:Reactive Oxygen Species / Q000737:chemistry; D012643:Selenium / Q000737:chemistry*
D000975:Antioxidants; D005609:Free Radicals; D016566:Organoselenium Compounds; D011725:Pyridines; D017382:Reactive Oxygen Species; D012643:Selenium; C023666:pyridine