Studies on Isoxazoles. XV. Syntheses of 3-Aminoisoxazole Derivatives

New versatile syntheses of 3-aminoisoxazoles and their derivatives are described. 3-(N, N-Disubstituted amino) isoxazoles 5 were synthesized by heating 3-chloro-2-methylisoxazolium chlorides 1 with secondary amines, or by the substitution reaction of 1 with primary amines, followed by the dehydrochl...

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Published inChemical & pharmaceutical bulletin Vol. 32; no. 2; pp. 530 - 537
Main Authors SUGAI, SOJI, SATO, KAZUO, KATAOKA, KUMIKO, IWASAKI, YUKIKO, TOMITA, KAZUO
Format Journal Article
LanguageEnglish
Published Tokyo The Pharmaceutical Society of Japan 1984
Maruzen
Japan Science and Technology Agency
Subjects
addition-elimination reaction
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Organic chemistry
Preparations and properties
Hydrolysis
Five membered ring
Aniline
Amidoxime
Thermal reaction
Hydrazine
Primary amine
Secondary amine
Oxygen nitrogen heterocycle
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Summary:New versatile syntheses of 3-aminoisoxazoles and their derivatives are described. 3-(N, N-Disubstituted amino) isoxazoles 5 were synthesized by heating 3-chloro-2-methylisoxazolium chlorides 1 with secondary amines, or by the substitution reaction of 1 with primary amines, followed by the dehydrochlorination and the subsequent addition-elimination reaction of alkyl or acyl halides with the resulting imines 6. Among the products 5, 3-(N-substituted acetylamino) isoxazoles were hydrolyzed with base to give 3-(N-monosubstituted amino) isoxazoles 3. 3-Aminoisoxazoles 7 were synthesized by the reaction of 1 with potassium phthalimide, followed by treatment with hydrazine.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.32.530