Facile synthesis of N-(1-alkenyl) derivatives of 2,4-pyrimidinediones.
N-(1-alkenyl) derivatives of 2,4-pyrimidinediones (6-9) were prepared in a one pot synthesis from aldehydes and the nucleobases using trimethylsilyl trifluoromethanesulfonate (TfOTMS) as coupling reagent. Presilylation of the above nucleobases, and N6-benzoyladenine, with excess N,O-bis(trimethylsilyl)acetamide (BSA) followed by addition of one mol eq. TfOTMS yielded the N-(1-trimethylsilyloxyalkyl) derivatives 1-5.
Henriksen
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Department of Chemistry, University of Copenhagen, H. C. Orsted Institute, Denmark.
D000225:Adenine / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D000998:Antiviral Agents / Q000138:chemical synthesis; D007096:Imidoesters / Q000737:chemistry; D008698:Mesylates / Q000138:chemical synthesis; D009711:Nucleotides / Q000737:chemistry; D011744:Pyrimidinones / Q000138:chemical synthesis*; D014297:Trimethylsilyl Compounds / Q000138:chemical synthesis / Q000737:chemistry
D000447:Aldehydes; D000998:Antiviral Agents; D007096:Imidoesters; D008698:Mesylates; D009711:Nucleotides; D011744:Pyrimidinones; D014297:Trimethylsilyl Compounds; C080718:N,O-bis(trimethylsilyl)acetamide; C053353:trimethylsilyl trifluoromethanesulfonate; D000225:Adenine