Studies on isoxazoles. VIII. Versatile syntheses and chemical properties of 3-chloroisoxazolium chlorides

The reaction of 4-isoxazolin-3-ones with phosgene or trichloromethyl chloroformate gave various 3-chloroisoxazolium chlorides in good yields, and these were converted to 4-isoxazolin-3-thiones on treatment with sodium hydrosulfide. Pyrolysis of 3-chloro-2-methylisoxazolium chlorides afforded 3-chlor...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 27; no. 10; pp. 2398 - 2404
Main Authors Tomita, K, Sugai, S, Kobayashi, T, Murakami, T
Format Journal Article
LanguageEnglish
Published Tokyo The Pharmaceutical Society of Japan 1979
Japan Science and Technology Agency
Subjects
agricultural products
condensation reaction
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Summary:The reaction of 4-isoxazolin-3-ones with phosgene or trichloromethyl chloroformate gave various 3-chloroisoxazolium chlorides in good yields, and these were converted to 4-isoxazolin-3-thiones on treatment with sodium hydrosulfide. Pyrolysis of 3-chloro-2-methylisoxazolium chlorides afforded 3-chloroisoxazoles. In the presence of tri-n-butylamine, 3-chloro-2-methyl-5-phenylisoxazolium chloride condensed carboxylic acids with alcohols or amines to give the corresponding esters or amides in high yields, together with 2-methyl-5-phenyl-4-isoxazolin-3-one.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.27.2398