Photoreaction of 2'-Halobenzanilide: Synthesis of 2-Phenylbenzoxazole

  • Ahmed M. Mayouf (Kyungpook National University, Department of Chemistry) ;
  • Park, Yong-Tae (Kyungpook National University, Department of Chemistry)
  • 발행 : 2000.03.01

초록

Irradiation of 2'-bromobenzanilide in acetonitrile containing sodium hydroxide under nitrogen leads to the formation of the intramolecular photosubstituted product, 2-phenylbenzoxazole (45 %) along the minor photoreduced and photo-Fries type product. The photoreaction of 2'chlorobenzanilide under the same condition as above gives the photo-Fries type reaction product, 2-amino-3-chlorobenzophenone (22%) with minor product, 2-phenylbenzoxazole. The photoreaction of 2'-chlorobenzanilide in acetonitrile produces a photocyclized product, phenanthridone (19%) along with minor products, 2-phenylbenzoxazole, benzanilide, 2-amino-3-chlorobenzophenone, and 4-amino-3-chlorobenzophenone, while that of 2'-bromobenzanilide produces photosubstituted product, 2- phenylbenzoxazole.

키워드

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