- Umpolung of Reactivity at the C-5 Position of Uracil: Facile Nucleophilic Reactions of Thiolate Ions at C-5 of 6-Cyano-1,3-dimethyluracil to Procure 5-Alkyl or 5-aryl-thio-1,3-dimethyluracils
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1,3-Dimethyluracil-6-carbonitrile 1 with thiolate ions generated in situ from thioiminium salts or thiols under phase transfer catalytic conditions undergoes umpolung of reactivity at C-5 to give 5-alkyl- or 5-aryl-thio-1,3-dimethyluracils as the major or sole products.However, propane-1,3-dithiol causes reductive decyanation of 1 to 1,3-dimethyluracil.
- Kumar, Subodh,Chimni, Swapandeep Singh
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p. 449 - 452
(2007/10/02)
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- 'UMPOLUNG' OF REACTIVITY AT C-5 POSITION OF URACIL: AN UNPRECEDENTED NUCLEOPHILIC REACTION OF THIOLATE ION AT C-5 OF 6-CYANO-1,3-DIMETHYLURACIL
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The soft thiolate ions react with 6-cyano-1,3-dimethyluracil at C-5 to give 5-alkylthio-1,3-dimethyluracil derivatives as major products.
- Kumar, Subodh,Chimni, Swapandeep Singh
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p. 2523 - 2526
(2007/10/02)
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