Abstract

Oxidative Coupling of 5‐Aminopyrazoles with p‐PhenylenediaminesBy oxidative coupling of 5‐amino‐3‐methyl‐1‐phenyl‐pyrazole 4 with N,N‐diethyl‐p‐phenylenediamine the 4‐(4‐N,N‐diethylamino‐phenylimino)‐3‐methyl‐1‐phenyl‐2‐pyrazolin‐5‐imin 5 is formed. 5 is oxidized very easily to the 1H‐pyrazolo[3,4‐b]quinoxaline 6a. The Z/E‐isomerism of the azomethine dye is investigated by dynamic n.m.r.‐spectroscopy. 1H‐Pyrazolo[3,4‐b]quinoxalines (6a–d) are also formed by reaction of 1,3‐disubstituted 5‐aminopyrazoles with p‐nitroso‐dialkylanilines.

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