70310-25-7Relevant academic research and scientific papers
Enantioselective Biocatalytic Reduction of 2 H-1,4-Benzoxazines Using Imine Reductases
Zumbr?gel, Nadine,Machui, Paul,Nonnhoff, Jannis,Gr?ger, Harald
, p. 1440 - 1447 (2019/02/07)
A biocatalytic reduction of 2H-1,4-benzoxazines using imine reductases is reported. This process enables a smooth and enantioselective synthesis of the resulting cyclic amines under mild conditions in aqueous media by means of a catalytic amount of the cofactor NADPH as hydride source as well as glucose as the reducing agent used in stoichiometric amounts for in situ cofactor recycling. Several substrates were studied, and the 3,4-dihydro-2H-1,4-benzoxazines were obtained with up to 99% ee. In addition, the efficiency of this reduction process based on imine reductases as catalysts has been demonstrated for one 2H-1,4-benzoxazine on an elevated laboratory scale running at a substrate loading of 10 g L-1 in the presence of a tailor-made whole-cell catalyst.
Oxidation and Photochemical Reactions of 3-Phenyl-2H-1,4-Benzoxazines
Battistoni, P.,Bruni, P.,Fava, G.,Tosi, G.
, p. 451 - 455 (2007/10/02)
3-Phenyl-2H-1,4-benzoxazines 4-oxides are light sensitive compounds, irradiation leads to 3-phenyl-2H-1,4-benzoxazines and to their 3-oxidized derivatives, whenever possible.Intermediate oxaziridines are formed during the photolysis and transformed into stable nitroxide radicals.The structure of these radicals was confirmed through peracid oxidation of 3-phenyl-2H-1,4-benzoxazines and 3-phenyl-3,4-dihydro-2H-1,4-benzoxazines.A reaction mechanism is proposed on the basis of experimental observations.
