A New Route to the Improved Synthesis of 1-(Alkoxymethyl)-5-alkyl- 6-(arylselenenyl)uracils

Namkyu Lee, Young Woo Kim, Key H. Kim, Dae Kee Kim

Research output: Contribution to journalArticlepeer-review

5 Scopus citations


A new route to C-6-selenenyl analogs of compound 1a from 5-alkyl-6-chlorouracils 6a-b has been described. A mild and highly efficient synthesis of 1-(alkoxymethyl)-5-alkyl-6-(arylselenenyl)uracils 8a-e has been accomplished from 6a-b in good yields using a two step procedure. Silylation of 5-alkyl-6-chlorouracils 6a-b using N,O-bis(trimethylsilyl)acetamide followed by regioselective alkylation of the silylated intermediate with ethyl or benzyl chloromethyl ether in dichloromethane afforded the desired 1-(alkoxymethyl)-5-alkyl-6-chlorouracils 7a-d in 88-94% yields. Compounds 7a-d readily underwent addition-elimination reaction with an appropriate arylselenol in the presence of ethanolic sodium hyroxide to produce the corresponding 1-(alkoxymethyl)-5-alkyl-6-(arylselenenyl)uracils 8a-e in excellent yields (94-99%).

Original languageEnglish
Pages (from-to)659-663
Number of pages5
JournalJournal of Heterocyclic Chemistry
Issue number2
StatePublished - 1997


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