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3 Polish Journal of Chemistry

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A New Approach to Synthesis of Questiomycin A: Oxidative Cyclocondensation of ortho-Aminophenol

Giurg M., Wiech E., Piekielska K., Gębala M., Młochowski J., Wolański M., Ditkowski B., Peczyńska-Czoch W.

Polish Journal of Chemistry

2006

Vol. 80, nr 2

297-306

Oxidation of ortho-aminophenol (1) to 2-amino-3H-phenoxazin-3-one (2) by air,manganese( IV) oxide, hydrogen peroxide or tert-butylhydroperoxide in the presence of different activators including such enzymes as laccase and peroxidase was studied. The most effective oxidants were air/Co(salen), MnO2/2,6-dicarboxypyridine complex 3k, H2O2/ebselen, H2O2/2,2'-dicarbamoylphenyldiphenyl disenide and TBHP/diphenyl diselenides 4d and 4e. Laccase and peroxidase were less active agents. The six-electron cyclocondensation mechanism is discussed.

Hydroperoxide Oxidation of Benzylamines Catalyzed by Selenium Compounds

Brząszcz M., Kloc K., Młochowski J.

Polish Journal of Chemistry

2003

Vol. 77 / nr 11

1579-1586

Selenium(IV) oxide, poly(bis-1,2-phenylene) diselenide, bis[2-(N-benzisoselenazol- 3(2H)-onyl]diselenide and particularly 2-phenyl-1,2-benzisoselenazol-3(2H)-one (ebselen), were employed as the catalysts for hydrogen peroxide and t-butyl hydroperoxide oxidation of benzylamines. A reaction of primary amines proceeded via hydroxylamine and oxime, and the nitriles accompanied by imines, carboxylic acids and aldehydes were the final products. The secondary amines produced mainly the nitrones, while tetrahydroisoquinoline was dehydrogenated to isoquinoline.

Hyrdoperoxide Oxidation of Azomethines and Alkylarenes Catalyzed by Ebselen

Giurg M., Wójtowicz H., J. Młochowski J.

Polish Journal of Chemistry

2002

Vol. 76 / nr 4

537-542

2-Phenyl-1,2-benzisoselenazol-3(2H)-one (ebselen), known as glutathione peroxidase mimic, is found as an efficient catalyst for hydrogen peroxide and tert-butyl hydroperoxide oxidation of the azomethine group in azines, aldoximes, and methyl or methylene group in alkylarenes. Depending on the substrate used and the reaction conditions, the major products are aldehydes, ketones, carboxylic acids or their derivatives. It is postulated that ebselen is involved in the free-radical oxidation mechanism.