- Iodination and metal halogen exchange of aromatic compounds: An improved preparation of a key oxazolidinone antibiotic intermediate
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A new method for the preparation of a key intermediate for oxazolidinone antibiotic analogues is discussed. We have found that iodine-magnesium exchange can be used to prepare a dianion if a fluorine is present ortho to the aryl anion and that exchange ta
- Herrinton, Paul M.,Owen, Carolyn E.,Gage, James R.
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- 2-Fluoro-(oxid-thiopyran-4-yl)benzene derivatives
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Compounds that can be used in the synthesis of cyclic sulfur-containing oxazolidinone antibacterial agents include2-Methylpropyl [4-(3,6-dihydro-1,1-dioxido-2H-thiopyran-4-yl)-3-fluorophenyl]carbamate,4(R)-trans-[3-[3-Fluoro-4-(tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl 3-nitrobenzenesulfonate,1α,4β(S)-N-[[3-[3-Fluoro-4-(tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]propanarnide monohydrate,4(R)-3-[3-Fluoro-4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-5-(hydroxymethyl)-2-oxazolidinone,4(R)-[3-[3-Fluoro-4-(tetrahydro-1,1-dioxido-2H-thiopyran-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl 3-nitrobenzenesulfonate.
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- Process to prepare cyclic-sulfur fluorine containing oxazolidinones
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The invention is a process for the preparation of cyclic-sulfur fluorine containing oxazolidinone antibacterial agents which utilizes the important tetrahydrothiopyran-o-fluorinated carbamate of formula (IV)
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- Stereodivergent synthesis of sulfoxide-containing oxazolidinone antibiotics
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Carbamate 5 was prepared under mild conditions via a novel metal-halogen exchange procedure without competing benzyne formation. Selection of an appropriate oxidation/reduction sequence afforded access to either the cis- or trans-1-oxo-4-aryltetrahydrothi
- Gage, James R.,Perrault, William R.,Poel, Toni-Jo,Thomas, Richard C.
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p. 4301 - 4305
(2007/10/03)
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