Tetrahedron p. 4091 - 4102 (1989)
Update date:2022-08-05
Topics:
Simay, Antal
Prokai, Laszlo
Bodor, Nicholas
Oxidation of aryloxy-β-aminopropanols (1) with "activated" dimethylsulfoxide (DMSO) was found to provide a convenient "one-pot" method to synthesize aryloxy-β-aminoketo-oximes (3), without isolation of the unstable ketones 2.Assignment of Z and E stereoisomers of oximes 3 was based on 1H- and 13C-NMR studies.Spontaneous isomerisation of 3 was also observed and discussed.Dioxime derivatives 6 and 7 were first isolated as by-products in the oxidation of compounds 1 and an improved synthetic method for 6 was developed.The novel C-N oxidation step involved in the formation of 6 from 1 was rationalized on the basis of neighboring grou p effect.
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