| Autor: |
Inukai, Yoshinari, Oono, Yoshitsugu, Sonoda, Takaaki, Kobayashi, Hiroshi |
| Zdroj: |
Bulletin of the Chemical Society of Japan; February 1979, Vol. 52 Issue: 2 p516-520, 5p |
| Abstrakt: |
With the intention of achieving the selective ortho-disubstitution of F-aniline viaintramolecular nucleophilic cyclization, syntheses of some requisite intermediate (F-phenyl)amino compounds and (F-benzo)heterocyclic compounds were investigated. 2-Phenyl-F-benzoxazole, 2-phenyl-F-benzimidazole, and 2,3-dihydro-1,4-(F-denz)oxazin-3-one were obtained from the respective precursors: benz-F-anilide, N-(F-phenyl)benzamidine, and hydroxyacet-F-anilide. 2-Phenyl-F-benzothiazole was obtained by treating benz-F-anilide with phosphorus pentasulfide. Hydrolytic dehalogenation of haloacet-F-anilide failed to give hydroxyacet-F-anilide, but it was obtained successfully by catalytic debenzylation of benzyloxyacet-F-anilide. The reactions of iodoacet-F-anilide with silver nitrate and acetate yielded 2-nitrate and 2-acetate, respectively. The reaction with diamminesilver(I) nitrate resulted in a reductive deiodination which gave acet-F-anilide. This exceptional reactivity was ascribed to the strong electron-withdrawing effect of the F-phenyl group. |
| Databáze: |
Supplemental Index |
| Externí odkaz: |
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