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Reaction of substituted benzylideneacetylacetones with hydroxylamine hydrochloride
Author(s) -
Kurihara Takushi,
Sakaguchi Toshiko,
Hirano Hiroshi
Publication year - 1976
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.5570130354
Subject(s) - chemistry , hydroxylamine hydrochloride , hydroxylamine , acetic acid , hydrochloride , yield (engineering) , acetonitrile , methanol , nitro , medicinal chemistry , organic chemistry , alkyl , materials science , metallurgy
The reaction of α,β‐unsaturated β‐diketones, such as 3‐(o‐chloro, m ‐nitro, and o ‐nitrobenzylidene)acetylacetones (I, II, and III) with hydroxylamine hydrochloride was carried out. Among them, compound I and II in acetonitrile, methanol, and acetic acid afforded 4‐(α‐hydroxy, methoxy, acetoxy, and chlorobenzyl)‐3,5‐dimethylisoxazoles (IV‐XI) in fairly good yield. On the other hand, III yielded 3‐(3′,5′‐dimethylpyrazolo)‐5‐chloroanthranil (XV) under the almost same conditions by the participation of o ‐nitro group.