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- W2049666430 abstract "Several methods have been developed for the preparation of β-lactams from isothiazolidinones. Oxidation of 2-t-butyl-4,4-diphenyl- and 2,4,4-trimethyl-isothiazolidin-3-ones (4a) and (4b) with sulphuryl chloride afforded the 5-chloroisothiazolidinones (5a) and (5b), which were converted into 1-t-butyl-3,3-diphenyl- and 1,3,3-trimethyl-4-phenylthioazetidin-2-ones (6a) and (6b) by treatment with phenyl-lithium. Alternatively, reaction of the isothiazolidinones (4a) and (4b) with phenyl-lithium gave N-t-butyl-2,2-diphenyl- and N,2,2-trimethyl-3-phenylthiopropionamides (12a) and (12b), which were transformed into the p-lactams (6a) and (6b) by halogenation at C-3, followed by treatment with potassium amide. These are examples of methods used to prepare β-lactams from isothiazolidinones. The versatility of these reactions and their relevance to penicillin biosynthesis is discussed." @default.
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- W2049666430 date "1985-01-01" @default.
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- W2049666430 title "Syntheses of β-lactams by ring contraction of isothiazolidinones" @default.
- W2049666430 doi "https://doi.org/10.1039/p19850000153" @default.
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