A novel and effective synthesis of substituted 1,4-benzoxazinones via Smiles rearrangement is described. Treatment of N-substituted 2-chloroacetamide, substituted 2-chlorophenols and cesium carbonate in refluxing DMF afforded the corresponding substituted 1,4-benzoxazinones in excellent yield.

Microwave-assisted Synthesis of 2H-Benz이이[1,4]oxazin-3(4丑)-ones and 1H-Pyrid이2,3-이 [1,4]oxazin-2(3H)-ones via Smiles Rearrangement

Oxazine derivatives R 0595 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 SmilesRearrangement. -The synthesis of benzo-fused oxazinones (IV) and pyrido-fused oxazinones (VII) is achieved by conventional heating and microwave irradiation. Treatment of substituted 2-chlorophenols (I) or 2-chloropyridol (V) with chloroacetamides (II) in the presence of potassium carbonate and subsequent exposure to cesium carbonate afford the title compounds via Smiles rearrangement. -(HUA, Z.; KAM, K.-H.; KWON, H.-J.; MENG, L.; AHN, C.; WON, T.-J.; KIM, T.-H.; REDDY, C. R.; CHANDRASEKHAR, S.; SHIN*, D.-S.; Bull. Korean Chem.