Efficient one-pot synthesis of polysubstituted 6-[(1H-1,2,3-triazol-1-yl)methyl]uracils through the "click" protocol
Petr Jansa*, Petr Špaček, Ivan Votruba, Petra Břehová, Martin Dračínský, Blanka Klepetářová and Zlatko Janeba
*Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic, Email: Petr.Jansagilead.com
P. Jansa, P. Špaček, I. Votruba, P. Břehová, M. Dračínský, B. Klepetářová, Z. Janeba, Collect. Czech. Chem. Commun., 2011, 13, 1121-1131.
DOI: 10.1135/cccc2011074 (free Supporting Information)
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The use of a stoichiometric amount of copper iodide enabled an efficient azide alkyne cycloaddition for the preparation of several triazolo acyclic nucleosides and triazolo acyclic nucleoside phosphonates. Using a catalytic amount of CuI, this reaction was slow, due to chelate-like complexation of the copper catalyst with the product. A simple work-up with Na2S is based on the low solubility of CuS.
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proposed structure of the complex of 6-[(1H-1,2,3-triazol-1-yl)methyl]uracils with copper