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Pyridazines. IV. The synthesis and some reactions of acetylpyridazines
Author(s) -
Nakagome Takenari,
Castle Raymond N.
Publication year - 1968
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570050312
Subject(s) - chemistry , nitration , oxide , furoxan , pyridazine , yield (engineering) , medicinal chemistry , inorganic chemistry , nitric oxide , organic chemistry , materials science , metallurgy
Two 3‐acetylpyridazines have been prepared. N ‐Oxidation of 3‐acetylpyridazine ( 6 ) gave only 3‐acetylpyridazine 1‐oxide ( 7 ). During the N ‐oxidation of 3‐acetyl‐6‐methoxypyridazine ( 10 ), three primary products, namely, 3‐acetyl‐6‐methoxypyridazine 1‐oxide ( 12 ), 3‐acetyl‐6‐methoxy‐pyridazine 2‐oxide ( 13 ), 3‐acetylpyridazin‐6‐one ( 14 ) and an artifact, 3‐methoxypyridazine 1‐oxide ( 15 ) were obtained. Furthermore, it has been shown that 3‐methoxypyridazine 1‐oxide ( 15 ) can be obtained in quantitative yield by treatment of 3‐acetyl‐6‐methoxypyridazine 2‐oxide ( 13 ) with dilute sodium hydroxide solution at room temperature. This represents a novel deacylation reaction. Nitration of 3‐acetylpyridazine 1‐oxide, ( 7 ) gave 3,4‐bis(3′‐pyridazinoyl)furoxan 1′,1′‐dioxide ( 19 ) rather than a simple nitration product. 3‐Acetyl‐pyridazine ( 6 ) and 3‐acetyl‐6‐methoxypyridazine ( 10 ) also gave furoxans ( 22 and 23 ) upon nitration.