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- W2950862613 abstract "Thermolysis of p-nitrobenzyl 6β-tritylaminopenicillanate 1β-oxide (1) afforded (2R)-3-methyl-2-(4-oxo-5-tritylimino-3-thiazolidinyl)-3-bute- noate (8), which could be easily converted into 4,5-dioxothiazolidines (9, 11). The influence of catalytic amounts of 2-mercaptobenzothiazole in promoting the rearrangement, and the isolation of the thiazolidinone (10) from thermolysis of a model azetidinone (17), suggest that the unusual scission of the C-5, C-6 bond originally present in penam (1) occurred at the level of tritylamino-1,2-secopenicillanates. A mechanism is proposed after the observation that the 6a-deuteriated penam (2) rearranged to the undeuteriated thiazolidinone (8), whilst epimeric 2-deuterio derivatives (18) were produced from (1) in the presence of D 2 O" @default.
- W2950862613 created "2019-06-27" @default.
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- W2950862613 date "1994-01-01" @default.
- W2950862613 modified "2023-10-17" @default.
- W2950862613 title "From Penicillins to 4,5-Dioxothiazolidines: A Thermal Rearrangement of Tritylaminopenam Derivatives" @default.
- W2950862613 doi "https://doi.org/10.3987/com-93-6652" @default.
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