Unexpected formation of 2′-deoxy-N3-(3,3,3-trifluoro-1-propenyl)uridine via a Michael-type addition to 3,3,3-trifluoropropyne

Panadda Chirakul, Snorri Th Sigurdsson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

Reaction of 3,3,3-trifluoropropyne with 2′-deoxy-5-iodouridine under conditions that have previously been used to prepare 5-alkynyl-2′-deoxyuridine derivatives gave 2′-deoxy-N3-(3,3,3-trifluoro-1-propenyl)uridine. This unexpected alkylation is a result of a Michael-type addition of N3 on the pyrimidine base to the electron deficient trifluoropropyne.

Original languageEnglish
Pages (from-to)6899-6901
Number of pages3
JournalTetrahedron Letters
Volume44
Issue number36
DOIs
Publication statusPublished - 1 Sept 2003

Bibliographical note

Funding Information:
This work was supported by the National Institutes of Heath (GM 58914). The authors thank V. Pons for technical assistance (Schlenk line) and helpful discussions, and Dr. M. Sadilek for assistance with LC/MS analyses.

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