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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 29, Number 7
BKCSDE 29(7)
July 20, 2008 

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
Zuo Hua, Kyeong-Hee Kam, Hee-Jin Kwon, Lijuan Meng, Chuljin Ahn, Tae-Jin Won, Tae-Hyun Kim, Ch. Raji Reddy, S. Chandrasekhar*, Dong-Soo Shin*
Microwave-assisted reaction, Benzo[1,4]oxazinone, Pyrido[1,4]oxazinone, Smiles rearrangement
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.
1379 - 1385
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