Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Microwave-assisted Synthesis of 2H-Benzo[b][1,4]oxazin-3(4H)-ones and 1H-Pyrido[2,3-b][1,4]oxazin-2(3H)-ones via Smiles Rearrangement

  • Hua, Zuo (Department of Chemistry, Changwon National University) ;
  • Kam, Kyeong-Hee (Department of Chemistry, Changwon National University) ;
  • Kwon, Hee-Jin (Department of Chemistry, Changwon National University) ;
  • Meng, Lijuan (Department of Chemistry, Changwon National University) ;
  • Ahn, Chul-Jin (Department of Chemistry, Changwon National University) ;
  • Won, Tae-Jin (Department of Chemistry, Changwon National University) ;
  • Kim, Tae-Hyun (Department of Chemistry, University of Incheon) ;
  • Reddy, Ch. Raji (Organic Chemistry Division-I, Indian Institute of Chemical Technology) ;
  • Chandrasekhar, S. (Organic Chemistry Division-I, Indian Institute of Chemical Technology) ;
  • Shin, Dong-Soo (Department of Chemistry, Changwon National University)
  • Published : 2008.07.20
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Abstract

Highly efficient synthesis of substituted benzo[1,4]oxazin-3-ones and pyrido[1,4]oxazin-2-ones under microwave irradiation via Smiles rearrangement is reported. Substituted benzo[1,4]oxazin-3-ones and pyrido[1,4]oxazin-2-ones were obtained by treatment of substituted 2-chlorophenols or 2-chloropyridols with N-substituted 2-chloroacetamide in the presence of potassium carbonate in MeCN and subsequent exposure to cesium carbonate in DMF. All the reactions which take 2-10 hours under conventional condition were completed successfully within a few minutes under microwave irradiation giving moderate to excellent yields.

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References

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