One-Pot Synthesis of N-Alkyl Purine, Pyrimidine and Azole
Derivatives from Alcohols using Ph3P/CCl4:
A Rapid Route to Carboacyclic Nucleoside Synthesis

Mohammad Navid Soltani Rad; Ali Khalafi-Nezhad; Somayeh Behrouz; Zeinab Asrari; Marzieh Behrouz; Zohreh Amini

doi:10.1055/s-0029-1216887

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Synthesis 2009(18): 3067-3076
DOI: 10.1055/s-0029-1216887

PAPER

One-Pot Synthesis of N-Alkyl Purine, Pyrimidine and Azole Derivatives from Alcohols using Ph₃P/CCl₄: A Rapid Route to Carboacyclic Nucleoside Synthesis

Mohammad Navid Soltani Rad*^a, Ali Khalafi-Nezhad*^b, Somayeh Behrouz^b, Zeinab Asrari^b, Marzieh Behrouz^b, Zohreh Amini^a
^a Department of Chemistry, Faculty of Basic Sciences, Shiraz University of Technology, Shiraz 71555-313, Iran
Fax: +98(711)7354523; e-Mail: soltani@sutech.ac.ir, nsoltanirad@gmail.com;
^b Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran

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Publication History

Received 21 April 2009
Publication Date:
07 July 2009 (online)

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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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