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Synthesis 2009(21): 3579-3588  
DOI: 10.1055/s-0029-1216982
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Propargyl-Substituted Phosphonocarboxylates: Efficient Synthesis and Application to Click Chemistry

Oleg I Artyushina, Sergey N. Osipova, Gerd-Volker Röschenthalerb, Irina L. Odinets*a
a A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova str., 119991 Moscow, Russian Federation
Fax: +7(499)1355085; e-Mail: odinets@ineos.ac.ru;
b Institute of Inorganic & Physical Chemistry, University of Bremen, Leobener Str., 28334 Bremen, Germany
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Publication History

Received 6 March 2009
Publication Date:
28 August 2009 (online)

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Abstract

An efficient pathway for the selective preparation of monopropargyl-substituted phosphonocarboxylate (PC) has been developed via the addition of sodium acetylenide to ethylidenephosphonate. The reaction works perfectly on multi-gram scales. The synthesis of the corresponding methyl(propargyl)-, trifluoro­methyl(propargyl)-, and dipropargyl-substituted derivatives was elaborated based on direct alkylation of either the correspondingly substituted phosphonocarboxylates or methylene phosphonocarboxylate with excess of propargyl bromide. A series of novel potentially biologically active 1,2,3-triazole-containing phosphono­-carboxylates were synthesized using copper(I)-catalysed 1,3-dipolar cycloaddition of organic azides with propargyl-substituted phosphonocarboxylates.

Key words

phosphonocarboxylates - ethylidenephosphonate - alkylation - sodium acetylenide - 1,3-dipolar cycloaddition - azides - phosphorylated 1,2,3-triazoles

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