SYNTHESIZE 1,3,5-SUBSTITUTED ISOXAZOLES AT EXCESSIVE BENZOYLATION OF β-AMINOPROPIOAMIDOXIMES IN PYRIDINE

Excessive acylation of β-aminopropioamidoximes (β-amino group: piperidin-1-yl, morpholin-1-yl, benzimidazol-1-yl, 4-phenylpiperazin-1-yl, thiomorpholin1-yl) was carried out with a doubling excess of benzoyl chloride in pyridine at the boiling point of the solvent for 4–8 h. The isolated products are: N,O-dibenzoyl-β-aminopropioamidoxime dihydrochlorides in the case of еркуу ашкые amidoximes, respectively. Chloride hydrate of 2-amino-1-aza-7-phenylaminospiro(4.5)decane-2-ene-10-ammonium and benzoic acid were the isolated products at using as starting amidoxime β-(4-phenylpiperazin-1-yl)propioamidoxime and hydrochloride of O-benzoyl-β-(thiomorpholin-1yl)propioamidoxime at using of β-(thiomorpholin-1-yl)propioamidoxime as substrate. The formation of 2-amino-1-aza-7-phenylaminospiro(4.5)decane-2-ene-10-ammonium chloride monohydrate can be represented as the initial formation of O-benzoyl-β-aminopropioamidoxime hydrochloride, its dehydration to 1,2,4-oxadiazole, and the subsequent passing of the Boulton-Katritazky rearrangement to form a spiropyrazolinium compound and benzoic acid.
References
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Topic: Structural and Chemical Analysis of Organic and Inorganic Compounds
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences