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

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.

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Synthesis and in vitro antimicrobial activity of benzo[b][1,4]thiazin-3(4H)-ones via smiles rearrangement

Yang

Fang

et al. 2009

Med Chem Res

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New benzo [b][1,4]thiazin-3(4H)-one derivatives (compounds 12a-p) were synthesized via Smiles rearrangement and assayed in vitro for their antimicrobial activity against Gram-positive, Gram-negative bacteria and fungi. The antimicrobial activity of the benzo[b][1,4]thiazin-3(4H)-ones showed, on the whole, potent toward all tested Gram-positive and Gram-negative microorganism (minimal inhibitory concentration ranging from 16 to 64 lg/ml), whereas weak effectiveness was exhibited against fungi. Data obtained suggested that 12g, 12i, and 12o exerted the best antibacterial activity against Grampositive bacteria and compound 12b demonstrated the best inhibition of Gram-negative bacteria. These observations provide some predictions to design further antimicrobial active compounds prior to their synthesis following with molecular modeling studies.

show abstract

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

Abstract: 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

Cited by 8 publications

References 22 publications

Microwaves in Heterocyclic Chemistry

Microwaves in Heterocyclic Chemistry

ChemInform Abstract: 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.

Synthesis and in vitro antimicrobial activity of benzo[b][1,4]thiazin-3(4H)-ones via smiles rearrangement

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