The Journal of Organic Chemistry

Nucleic acid related compounds. 39. Efficient conversion of 5-iodo to 5-alkynyl and derived 5-substituted uracil bases and nucleosides

MJ Robins, PJ Barr

Index: Robins, Morris J.; Barr, Philip J. Journal of Organic Chemistry, 1983 , vol. 48, # 11 p. 1854 - 1862

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Citation Number: 338

Abstract

Coupling of terminal alkynes with 5-iodo-1-methyluracil and 5-iodouracil nucleosides (protected as their p-toluyl esters) proceeded in high yields in the presence of bis (triphenylphosphine) palladium (II) chloride and copper (1) iodide in warm triethylamine. Several of the subsequently deprotected B-alkynyl-2'-deosyuridines, including the parent 5- ethynyl-2'-deoxyuridine, had antiviral activity, and their 5'-monophosphates inhibited ...