• Journal of the Korean Chemical Society
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• v.56 no.4
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• pp.468-472
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• 2012

Efficient one-pot microwave-assisted synthesis of various benzo-[1,4]-oxazinones via Smiles rearrangement is described. Treatment of 2-chloroacetamide, substituted 2-chlorophenols and cesium carbonate in MeO-PEG-OMe (2,000) as solvent afforded the corresponding benzo-[1,4]-oxazinones and 1H-pyrido[2,3-b][1,4]-oxazin-2-(3H)-one as moderate yield.

• Bulletin of the Korean Chemical Society
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• v.29 no.7
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• pp.1379-1385
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• 2008

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.