Bulletin of the Chemical Society of Japan p. 3447 - 3452 (1981)
Update date:2022-08-04
Topics:
Inukai, Yoshinari
Oono, Yoshitsugu
Sonoda, Takaaki
Kobayashi, Hiroshi
With the intention of achieving the selective ortho-substitution of F-benzoic acid and F-phenol via intramolecular nucleophilic cyclization, preparation of some requisite precursory F-benzoyl- and F-phenoxy compounds and their nucleophilic cyclization reactions were examined. 1,2-(F-Benz)isoxazol-3(2H)-one, 2-(p-tolyl)-1,2-(F-benz)isoxazol-3(2H)-one, 1,3-dimethyl(F-benzo)pyrimidine-2,4(1H,3H)-dione, and 1,4-(F-benz)oxazin-3(2H)-one were obtained from the respective precursory F-benzohydroxamic acid, N-(p-tolyl)-N-hydroxy-F-benzamide, N,N'-dimethyl-N-(F-benzoyl)urea, and 2-(F-phenoxy)acetohydrazide.Attempted cyclizations of 2-(F-phenoxy)acetohydroxamic acid and (F-phenoxy)acetic acid were accompanied by simultaneous ring-opening and resulted in the formation of the identical product : (2-hydroxy-F-phenoxy)acetic acid.Transamidation of ethyl F-benzoate with hydroxylamine failed to give F-benzohydroxamic acid, which was then obtained by the catalytic debenzylation of N-benzyloxy-F-benzamide.
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