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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. © 2013 Georg Thieme Verlag Stuttgart New York.

Registro:

Documento: Artículo
Título:1,3-dipolar cycloadditions of the versatile intermediate tetraethyl vinylidenebisphosphonate
Autor:Ferrer-Casal, M.; Barboza, A.P.; Szajnman, S.H.; Rodriguez, J.B.
Filiación:Departamento de Química Orgánica, UMYMFOR, Universidad de Buenos Aires, Pabellón 2, C1428EHA Buenos Aires, Argentina
Palabras clave:1,3-dipolar cycloadditions; azides; bisphosphonates; Grigg azomethine ylides; nitrile oxides; 1 ,3-dipolar cycloadditions; azides; Azomethine ylides; Bisphosphonates; Nitrile oxides; Nitrogen compounds; Nitrogen oxides; Cycloaddition; azide; bisphosphonic acid derivative; diethyl 4,4 bis(diethoxyphosphoryl) 5 (4 methoxyphenyl)pyrrolidine 2,2 dicarboxylate; diethyl 4,4 bis(diethoxyphosphoryl) 5 pentylpyrrolidine 2,2 dicarboxylate; diethyl 4,4 bis(diethoxyphosphoryl) 5 phenylpyrrolidine 2,2 dicarboxylate; ethyl 4,4 bis(diethoxyphosphoryl) 2 nitrobutanoate; nitrile oxide; octaethyl (3 nitropentane 1,1,5,5 tetrayl)tetrakis(phosphonate); tetraethyl vinylidenebisphosphonate; tetraethyl(1 benzyl 4,5 dihydro 1h 1,2,3 triazole 4,4 diyl)bisphosphonate; tetraethyl(3 methyl 4,5 dihydroisoxazole 5,5 diyl)bisphosphonate; tetraethyl(3 nitrobutane 1,1 diyl)bisphosphonate; tetraethyl(3 pentyl 4,5 dihydroisoxazole 5,5 diyl)bisphosphonate; tetraethyl(3 phenyl 4,5 dihydroisoxazole 5,5 diyl)bisphosphonate; tetraethyl[1 [2 (4 phenoxyphenoxy)ethyl] 4,5 dihydro 1h 1,2,3 triazole 4,4 diyl]bisphosphonate; tetraethyl[1 [2,2 bis(diethoxyphosphoryl)ethyl] 4,5 dihydro 1h 1,2,3 triazole 4,4 diyl]bisphosphonate; tetraethyl[2 (1h benzo[d][1,2,3]triazol 1 yl)ethane 1,1 diyl]bisphosphonate; tetraethyl[3 (4 methoxyphenyl) 4,5 dihydroisoxazole 5,5 diyl]bisphosphonate; unclassified drug; article; carbon nuclear magnetic resonance; complex formation; cycloaddition; Diels Alder reaction; drug structure; proton nuclear magnetic resonance
Año:2013
Volumen:45
Número:17
Página de inicio:2397
Página de fin:2404
DOI: http://dx.doi.org/10.1055/s-0033-1338498
Título revista:Synthesis (Germany)
Título revista abreviado:Synthesis
ISSN:00397881
CODEN:SYNTB
CAS:azide, 12596-60-0, 14343-69-2
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397881_v45_n17_p2397_FerrerCasal

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Citas:

---------- APA ----------
Ferrer-Casal, M., Barboza, A.P., Szajnman, S.H. & Rodriguez, J.B. (2013) . 1,3-dipolar cycloadditions of the versatile intermediate tetraethyl vinylidenebisphosphonate. Synthesis (Germany), 45(17), 2397-2404.
http://dx.doi.org/10.1055/s-0033-1338498
---------- CHICAGO ----------
Ferrer-Casal, M., Barboza, A.P., Szajnman, S.H., Rodriguez, J.B. "1,3-dipolar cycloadditions of the versatile intermediate tetraethyl vinylidenebisphosphonate" . Synthesis (Germany) 45, no. 17 (2013) : 2397-2404.
http://dx.doi.org/10.1055/s-0033-1338498
---------- MLA ----------
Ferrer-Casal, M., Barboza, A.P., Szajnman, S.H., Rodriguez, J.B. "1,3-dipolar cycloadditions of the versatile intermediate tetraethyl vinylidenebisphosphonate" . Synthesis (Germany), vol. 45, no. 17, 2013, pp. 2397-2404.
http://dx.doi.org/10.1055/s-0033-1338498
---------- VANCOUVER ----------
Ferrer-Casal, M., Barboza, A.P., Szajnman, S.H., Rodriguez, J.B. 1,3-dipolar cycloadditions of the versatile intermediate tetraethyl vinylidenebisphosphonate. Synthesis. 2013;45(17):2397-2404.
http://dx.doi.org/10.1055/s-0033-1338498