Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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An Intramolecular Photosubstitution Reaction of N-(2,4-Dibromonaphthyl)- arenecarboxamide: Synthesis of 2-Arylnaphthoxazole

  • Bae, In-Soo (Department of Chemistry, Kyungpook National University) ;
  • Kim, Yoo-Shin (Department of Chemistry, Kyungpook National University) ;
  • Park, Yong-Tae (Department of Chemistry, Kyungpook National University)
  • Published : 2003.07.20
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Abstract

Photoreactions of N-(2,4-dibromonaphthyl)arenecarboxamides in basic medium result in the intramolecular substituted products, 2-aryl-8-bromonaphthoxazoles in moderate yields and further photoreactions of the products afford the reduced products, 2-arylnaphthoxazoles. These reactions are straightforward for syntheses of naphthoxazole derivatives. Since the intramolecular photosubstitution of the bromoarenecarboxamide by the oxygen of its amide group is more effective than the photoreduction of the substituted product, 2-aryl-8- bromonaphthoxazole in basic medium, the intramolecular substituted product, 2-aryl-8-bromonaphthoxazole can be isolated. A charge-transfered excited singlet state of an imidol form of the 2-bromoarenecarboxamide is involved in the photosubstitution, whereas an excited triplet state of the 2-aryl-8-bromonaphthoxzole is closely involved in the photoreduction.

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References

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