Bulletin of the Korean Chemical Society

  • 제24권7호
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  • Pages.916-920
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  • 2003
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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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)
  • 발행 : 2003.07.20
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초록

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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참고문헌

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피인용 문헌

  1. Blue-Emitting Nanocrystals, Microcrystals, and Highly Oriented Nanofibers Prepared by Reprecipitation and Solvent Drop-Casting of 2-Phenyl-naphthoxazoles vol.78, pp.2, 2013, https://doi.org/10.1002/cplu.201200233
  2. ][1,3]oxazoles vol.78, pp.1, 2013, https://doi.org/10.1021/jo3022956
  3. Continuous flow photochemistry as an enabling synthetic technology: synthesis of substituted-6(5H)-phenanthridinones for use as poly(ADP-ribose) polymerase inhibitors vol.7, pp.4, 2016, https://doi.org/10.1039/C5MD00552C
  4. A Convenient Synthesis of 2-Arylnaphtho[1,2-d]oxazole Derivatives Promoted by Triethylamine vol.25, pp.11, 2007, https://doi.org/10.1002/cjoc.200790315
  5. An Intramolecular Photosubstitution Reaction of N-(2,4-Dibromonaphthyl)arenecarboxamide: Synthesis of 2-Arylnaphthoxazole. vol.34, pp.52, 2003, https://doi.org/10.1002/chin.200352132