1,3-Dipolar Cycloadditions of the Versatile Intermediate Tetraethyl Vinylidenebisphosphonate
2013; Thieme Medical Publishers (Germany); Volume: 45; Issue: 17 Linguagem: Inglês
10.1055/s-0033-1338498
ISSN1437-210X
AutoresSergio H. Szajnman, Juan B. Rodríguez, Mariana Ferrer‐Casal, Alejandro P. Barboza,
Tópico(s)Chemical Synthesis and Analysis
ResumoThe 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.
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