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Synthesis 2013; 45(17): 2397-2404
DOI: 10.1055/s-0033-1338498
DOI: 10.1055/s-0033-1338498
paper
1,3-Dipolar Cycloadditions of the Versatile Intermediate Tetraethyl Vinylidenebisphosphonate
Further Information
Publication History
Received: 06 May 2013
Accepted after revision: 31 May 2013
Publication Date:
10 July 2013 (online)
Abstract
The use of tetraethyl vinylidenebisphosphonate as a dipolarophile in 1,3-dipolar cycloaddition reactions was investigated. In particular, the cycloaddition reactions between tetraethyl vinylidenebisphosphonate and azides and nitrile oxides, and of tetraethyl vinylidenebisphosphonate in the Grigg azomethine 1,3-dipolar cyclization were studied, affording highly functionalized five-membered rings containing the bisphosphonic unit. These straightforward methods allow the preparation of diverse and fairly complex structures bearing the bisphosphonate moiety, which belong to a group of pharmacologically important compounds.
Key words
bisphosphonates - 1,3-dipolar cycloadditions - azides - nitrile oxides - Grigg azomethine ylidesSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis. Included are experimental procedures for the preparation of oximes 28–30, copies of 1H, 13C, and 31P NMR spectra for all the compounds synthesized, and selected 2D-NMR data.
- Supporting Information
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