THE REACTIVITY OF NITROPHENYL SUBSTITUTED CYCLIC AMINES WITH DEHYDROGENATIONS

Piperidine and perhydroazepine bearing a 1-(4-nitrophenyl) substituent were inert to mercuryedta, while the alpha-pipecoline derivative gave an aminoketone with cleavage of the heterocycle. However the correspo nding (2-nitrophenyl) compounds reacted to give respectively a piperid in-2-one, an aminopentanal and an aminohexanone. By an additional subs tituent in 2'-position the p-nitro compounds underwent dehydrogenation too. With a methyl group resulted a pattern analogous to o-nitro prod ucts. A neighbouring hydroxymethyl function enhanced the reaction with formation of benzoxazines and if possible their further oxidized deri vatives, the hydroxylactams.