Isoxazoles. XX. Base-induced Ring Cleavage Reactions of 2,3,4-Trisubstituted Isoxazolium Salts

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概要

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• Ring opening reactions with some bases were examined in the following quaternary salts : 2-ethyl-3,4-diphenylisoxazolium chloroferrate (V), and 2,4-dimethyl-3-phenyl-, 3,4-diphenyl-2-methyl- and 2-methyl-3-phenylisoxazolium perchlorate (IXa, b and c). Treatments of V and IX with sodium alcoholate in alcohol gave the corresponding alkyl cinnamates (VIIa-e). By the use of aqueous sodium hydroxide, V and IXb gave the respective cinnamic anhydrides (Xa and b) contrary to the report of Kohler, et al., and IXa gave an unexpected product, 2,5-diphenyl-1,3,4-trimethylpyrrole (XIa) along with usual ring cleaved products, XIIa and XIIIa. Reactions of IXa, b with several amines gave β-keto acid amides (XIIc-h), the ketones (XIIIa, b) and the pyrrole (XIa) (only from IXa), respectively. Reactions of IXa with Grignard reagents gave 5-substituted △^3-isoxazolines (XIVa, b). Similar 5-amino-△^3-isoxazolines (XVa-c) were obtained by cautious treatment of IXa, b with piperidine or morpholine. Solvolysis of X, XIV and XV were also investigated, and a tentative mechanism for the formation of the various products are presented.

• 公益社団法人日本薬学会の論文
• 1969-11-25

著者

• 足達 郁夫

  Shionogi Research Laboratories Shionogi & Co. Ltd.

• 加納 日出夫

  Shionogi Research Laboratory Shionogi & Co. Ltd.

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