Heterocyclole als Zwischenprodukte einer neuen, überraschenden Umlagerung bei der Reaktion von 3-(Dimethylamino)-2,2-dimethyl-2H-azirin mit monosubstituierten Parabansäuren

Abstract

Cyclols as Intermediates in the Reaction of 3-(Dimethylamino)-2,2-dimethyl-2H-azirine with Monosubstituted Parabanic Acids; a New and Unexpected Rearrangement. The reaction of 3-(dimethylamino)-2,2-dimethyl-2H-azirine (1) with N-methyl- parabanic acid (4) in 2-propanol at room temperature gives the cyclol 5 in 97% yield. In acetonitrile solution 5 rearranges to the imidazoline derivative 6 (Scheme 2). The structures of the unexpected products 5 and 6 have been established by X-ray crystallography.