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Sur l'amino-5-benzoyl-4-méthyl-3-isoxazole: synthèse et transformation en dihydro-6,8-diméthyl-3,8-phényl-4-7H-isoxazolo[5,4-e]diazépin-1,4-one-7

✍ Scribed by Roland Jaunin

Publisher
John Wiley and Sons
Year
1974
Tongue
German
Weight
568 KB
Volume
57
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

On treatment with ammonia and benzaldehyde the benzalisoxazolone 3 does not give the aminoketone 7 as assumed by Speroni [1] but a product which has been shown to be identical with the enamine 8 prepared by Ried & Czack [4] from ethyl oximinoacetoacetate and benziminoethyl ether. Authentic aminoketone 7 was synthesized in a three‐step procedure starting from the aminonitrile 19. Conversion of 7 into the bromacetyl derivative 23 and subsequent treatment with hexamethylene‐tetramine yielded the isoxazolodiazepine 24. Methylation of 24 with diazomethane produced predominantly the N‐methyl derivative 1 along with a small amount of the O‐methyl compound 25.

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