著者

加納 日出夫 足達 郁夫

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.16, no.1, pp.117-125, 1968-01-25 (Released:2008-03-31)

被引用文献数

6 12

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Nine bicyclic isoxazolines (IVa-g and Va-b) were prepared by 1, 3-dipolar cycloaddition of nitrile oxides to the following heterocyclic olefins : 2, 3-and 2, 5-dihydrofurans, 5-methyl-2, 3-dihydrofuran, 2, 3-dihydropyran, and N-acetyl-2-piperidein. Acid-catalized cleavage of IVa-d gave the corresponding 4-substituted 3-phenylisoxazoles (VIa-c and IIIg). Nine 4-aminoalkyl-3-phenylisoxazoles (IIIa-i) were prepared for pharmacological testings in comparison with those of 3- and 5-aminoalkyl analogs (I and II). Base-catalized cleavage of the adducts (IVa-c and Va) was also investigated and in some cases the lactones (XIIa and XIIb) were obtained besides the isoxazoles (VIa and VIb). In this connection the Hofmann reactions of the bicyclic isoxazoline-3-carbon-amides (IVe'and IVf') were studied.

著者

足達 郁夫 加納 日出夫

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.17, no.11, pp.2201-2208, 1969-11-25 (Released:2008-03-31)

被引用文献数

5 12

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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.

著者

足達 郁夫 宮崎 理慧 加納 日出夫

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.22, no.1, pp.70-77, 1974-01-25 (Released:2008-03-31)

被引用文献数

16 29

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Synthesis and thermal-reaction of 4-isoxazolines were investigated. Reaction of 3-unsubstituted isoxazolium salts with sodium borohydride yielded the corresponding 4-isoxazolines and their borane complexes together with β-hydroxyaminopropiophenone derivatives. Analogous reaction of 5-unsubstituted isoxazolium salt yielded two isomeric products, 4- and 3-isoxazoline derivatives. The 3-isoxazoline derivative underwent further reduction to give isoxazolidine derivatives. Thermal-conversion of some 4-isoxazolines and their borane complexes into 2-acylaziridine derivatives is also reported.