Quinoline is aminated into 2‐aminoquinoline (55‐60%) when treated with potassium amide/liquid ammonia/potassium permanganate at −65°. When the amination is carried out by allowing the solution of quinoline in potassium amide/liquid ammonia to raise from −60° to + 15° before addition of potassium permanganate, the main product is 4‐aminoquinoline. Using as reagent liquid ammonia/potassium permanganate (thus without the presence of potassium amide) 3‐nitroquinoline is exclusively aminated at −40° into 4‐amino‐3‐nitroquinoline. Using the same conditions, from 4‐nitroquinoline 3‐amino‐4‐nitroquinoline is obtained. The mechanism of these amination reactions is discussed.

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Treatment of 4‐nitropyridazine 1‐oxide (1a) 3‐methoxy‐6‐chloro‐4‐nitropyridazine 1‐oxide (1b) or 3,6‐dimethoxy‐4‐nitropyridazine 1‐oxide (1c) with a solution of potassium permanganate in liquid ammonia gives in reasonable‐to‐good yields the corresponding 5‐amino‐4‐nitropyridazine 1‐oxides (75%, 54% and 62%, respectively). 3,6‐Dimethoxypyridazine (4a) and 3‐methoxypyridazine (4b) are converted into the corresponding 4‐aminopyridazines 6a,6b on treatment with potassium amide/liquid ammonia/potassium permanganate (yield 50 and 22% respectively). In the last‐mentioned reaction besides 6b 3,3′‐dimethoxy 4,4′‐bipyridazine (7, 23%) was obtained. It is suggested that the neutral 1:1 σ‐adducts formed between (1a–1c) and liquid ammonia and the anionic σ‐adducts, formed between (5a–5b) and potassium amide are intermediates in this amino‐oxidation reaction.

Die bekannten biologischen Eigenschaften von Diaroylfuroxanen und Diaroylfurazano[d]pyridazin‐1‐oxiden geben Anlaß zu der Synthese der Furazane (III) und ihrer cyclischen Azine (IV).

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