Phenyl-, benzyl-, and unsymmetrical hydroxy-methylenebisphosphonates as dronic acid ester analogues from α-oxophosphonates by microwave-assisted syntheses

György Keglevich, Alajos Grün, István Gábor Molnár, István Greiner

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Abstract

The microwave (MW)-assisted addition of dialkyl phosphites to α-oxophosphonates was investigated and optimized under solventless conditions to provide the phenyl- and benzyl-hydroxy-methylenebisphosphonates efficiently by suppressing the rearrangement side reaction. Methyl-hydroxy- methylenebisphosphonates with mixed ester functionalities and an analogous diester-diacid were also synthesized. It was found that the α- oxophosphonates may also be converted to hydroxy-methylenebisphosphonates and/or rearranged products without using dialkyl phosphite as the reagent and with the careful exclusion of water, simply on standing at room temperature, on thermal treatment, or on MW irradiation. These novel reactions taking place via the controlled decomposition of the precursor and resulting in the intermediate formation of dialkyl phosphite were also studied in detail.

Original languageEnglish
Pages (from-to)640-648
Number of pages9
JournalHeteroatom Chemistry
Volume22
Issue number5
DOIs
Publication statusPublished - Sep 1 2011

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ASJC Scopus subject areas

  • Chemistry(all)

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