ACETALS OF LACTAMS AND AMIDES OF ACIDS. 72. INVESTIGATION OF REACTION OF CYCLIC β-NITROENAMINES WITH p-BENZOQUINONE

Article abstract of DOI:10.1007/BF00529373

The process of condensation of p-benzoquinone with the secondary cyclic enamines 2-(2-nitromethylene)pyrrolidine, -piperidine, and -hexahydroazepine is very much dependent on the size of the saturated ring in these compounds.With increasing ring size, the content of derivatives of 5-hydroxybenzofuran decreases, and the quantity of derivatives of 5-hydroxyindole increases; with the seven-membered enamine, a substituted 6-hydroxyindole is also formed.For enamines of the pyrrolidine and piperidine series, 1,4-bis-2-(2'-nitromethylene)pyrrolidono- or piperidinohydroquinones are also recovered.