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Synthesis 2009(18): 3067-3076
DOI: 10.1055/s-0029-1216887
DOI: 10.1055/s-0029-1216887
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkOne-Pot Synthesis of N-Alkyl Purine, Pyrimidine and Azole Derivatives from Alcohols using Ph3P/CCl4: A Rapid Route to Carboacyclic Nucleoside Synthesis
Further Information
Received
21 April 2009
Publication Date:
07 July 2009 (online)
Publication History
Publication Date:
07 July 2009 (online)
Abstract
A facile and efficient method for one-pot N-alkylation of nucleobases and azole derivatives from alcohols using triphenylphosphine in carbon tetrachloride is described. In this method, treatment of alcohols with a mixture of triphenylphosphine, carbon tetrachloride, nucleobase or azole derivatives and potassium carbonate in the presence of catalytic amounts of tetra-n-butylammonium iodide (TBAI) in refluxing N,N-dimethylformamide, furnishes the corresponding N-alkyl derivatives in good yields. This methodology is highly efficient for various structurally diverse primary alcohols and also useful for N-alkylation of other N-heterocycles containing an acidic N-H bond.
Key words
carboacyclic nucleosides - N-alkylation - nucleobase - alcohol - triphenylphosphine - carbon tetrachloride - potassium carbonate
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