An Efficient Synthesis of 4-Acyl-5-hydroxy-3-methylisoxazoles through an Acyl-Transfer Reaction

Acylation of 3-methyl-3-isoxazolin-5-one (2a) with acyl chlorides was investigated. 2-Acyl-3-methyl-3-isoxazolin-5-ones 5 and 5-acyloxy-3-methylisoxazoles 6, which were prepared from 2a and acyl halides, underwent acyl-transfer reaction in the presence of 4-(N, N-dimethylamino)-pyridine or potassium...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 34; no. 8; pp. 3153 - 3158
Main Authors SATO, KAZUO, UEDA, TAKASHI, SUGAI, SOJI
Format Journal Article
LanguageEnglish
Published TOKYO The Pharmaceutical Society of Japan 1986
Pharmaceutical Soc Japan
Maruzen
Japan Science and Technology Agency
Subjects
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Life Sciences & Biomedicine
Organic chemistry
Pharmacology & Pharmacy
Physical Sciences
Preparations and properties
rearrangement
Science & Technology
One pot reaction
Five membered ring
Transfer reaction
Base catalysis
Acyl chloride
Acylation
Oxygen nitrogen heterocycle
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Summary:Acylation of 3-methyl-3-isoxazolin-5-one (2a) with acyl chlorides was investigated. 2-Acyl-3-methyl-3-isoxazolin-5-ones 5 and 5-acyloxy-3-methylisoxazoles 6, which were prepared from 2a and acyl halides, underwent acyl-transfer reaction in the presence of 4-(N, N-dimethylamino)-pyridine or potassium carbonate to give 4-acyl-5-hydroxy-3-methylisoxazoles 4. By using this reaction, 4-(2, 4-dichlorobenzoyl)-5-hydroxy-3-methylisoxazole (4h), which can be viewed as a bioisostere of the herbicidal compound, 4-(2, 4-dichlorobenzoyl)-1, 3-dimethyl-5-hydroxypyrazole (1a), was synthesized.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.34.3153