1071869-57-2Relevant academic research and scientific papers
Catalytic hydrogenation of 5,6-dihydro-4H-1,2-oxazines bearing a functionalized methylene group at C-3
Sukhorukov, Alexey Yu.,Lesiv, Alexey V.,Eliseev, Oleg L.,Khomutova, Yulia A.,Ioffe, Sema L.,Borissova, Alexandra O.
experimental part, p. 4025 - 4034 (2009/04/14)
The catalytic hydrogenation of readily available methyl 2-(5,6-dihydro-4H-1,2-oxazin-3-yl)acetates 6 has been studied. Dihydrooxazines 6 without an alkoxy substituent at C-6 under mild hydrogenation conditions in methanol produce a dynamic mixture of enamines 7 and tetrahydro-2-furanamines 7′(α+β). These products can be transformed into 1,4-amino alcohols 8 under more robust hydrogenation conditions or into isomeric dihydrofurans 9 and 10 if the reduction is carried out in glacial acetic acid. Reduction of dihydrooxazines 6h,i, which possess an alkoxy substituent at C-6, under similar conditions affords pyrrolidine derivatives 12, 13 and 14. A general mechanistic scheme for the hydrogenation reaction that involves an initial N-O bond cleavage has been suggested. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
