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Abstract:

1,2-Dicyano-4,5-di[(N,N-dimethylaminocarbonyl)methoxy]benzene (5) was synthesized in 80% yield from the corresponding 1,2-dibromo derivative 4. Octa(peripheral-amide)substituted zinc(II) phthalocyanine 6 was obtained from 5 and zinc acetate in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene. Phthalocyanine 7 was prepared via reduction of 6 with diborane. Treatment of 7 with methyl iodide afforded cationic dye 8. © Georg Thieme Verlag Stuttgart.

Registro:

Documento: Artículo
Título:Reduction of an amido zinc(II) phthalocyanine by diborane
Autor:Strassert, C.A.; Dicelio, L.E.; Awruch, J.
Filiación:Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956, 1113 Buenos Aires, Argentina
Departamento de Química Inorgánica, Analítica y Química Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina
Palabras clave:Nucleophilic aromatic substitution; Phthalocyanines; Reduction; Dyes; Positive ions; Nucleophilic aromatic substitution; Phthalocyanines; Reduction; Semiconducting zinc compounds; 1,2 dicyano 4,5 di[(n,n dimethylaminocarbonyl)methoxy]benzene; 1,8 diazabicyclo[5.4.0]undec 7 ene; 2,3,9,10,16,17,23,24 octakis[(n,n dimethylaminocarbonyl)methoxy]phthalocyaninatozinc(ii); 2,3,9,10,16,17,23,24 octakis[(n,n dimethylaminoethoxy)]phthalocyaninatozinc(ii); 2,3,9,10,16,17,23,24 octakis[(n,n,n triethylammonium)ethoxy]phthalocyaninatozinc(ii)octaiodide; amido zinc(ii) phthalocyanine; benzene derivative; heterocyclic compound; phthalocyanine derivative; unclassified drug; zinc acetate; article; drug synthesis; matrix assisted laser desorption ionization time of flight mass spectrometry; proton nuclear magnetic resonance; reduction; substitution reaction
Año:2006
Número:5
Página de inicio:799
Página de fin:802
DOI: http://dx.doi.org/10.1055/s-2006-926336
Título revista:Synthesis
Título revista abreviado:Synthesis
ISSN:00397881
CODEN:SYNTB
CAS:zinc acetate, 557-34-6
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00397881_v_n5_p799_Strassert

Referencias:

  • (1989) Phthalocyanines, Properties and Applications, 1-4. , Leznoff, C. C.; Lever, A. B. P., Eds.; VCH: New York, 1993
  • McKeown, N.B., (1998) Phthalocyanine Materials: Synthesis, Structure and Function, , Cambridge University Press: Cambridge
  • Dini, D., Barthel, M., Schneider, T., Ottmar, M., Verma, S., Hanack, M., (2003) Solid State Ionics, 165, p. 289
  • Martinez-Diaz, M.V., Esperanza, S., De La Escosura, A., Catellani, M., Yunus, S., Luzzati, S., Torres, T., (2003) Tetrahedron Lett., 44, p. 8475
  • Lever, A.B.P., (2004) J. Porphyrins Phthalocyanines, 8, p. 1327
  • Hasrat, A., Van Lier, J.E., (1999) Chem. Rev., 99, p. 2379
  • Pandey, R.K., (2000) J. Porphyrins Phthalocyanines, 4, p. 368
  • MacDonald, I.J., Dougherty, T.J., (2001) J. Porphyrins Phthalocyanines, 5, p. 105
  • Detty, M.R., Gibson, S.L., Wagner, S.J., (2004) J. Med. Chem., 47, p. 3897
  • Uchida, H., Reddy, P.Y., Nakamura, S., Toru, T., (2003) J. Org. Chem., 68, p. 8736. , and references cited therein
  • Leznoff, C.C., Vigh, S., Svirskaya, P.I., Greenberg, S., Drew, D.M., Ben-Hur, E., Rosenthal, I., (1989) Photochem. Photobiol., 49, p. 279
  • Fernández, D.A., Awruch, J., Dicelio, L.E., (1997) J. Photochem. Photobiol., B, 41, p. 227
  • De Filippis, M.P., Dei, D., Fantetti, L., Roncucci, G., (2000) Tetrahedron Lett., 41, p. 9143
  • Sugimori, T., Nojima, J., Ozawa, T., Handa, M., Kasuga, K., (2004) Chem. Lett., 33, p. 1014
  • Ramirez, C., Antonacci, C., Ferreira, J., Sheardy, R.D., (2004) Synth. Commun., 34, p. 3373
  • Andersen, M.E., Barret, A.G.M., Hoffman, B.M., (1999) Inorg. Chem., 38, p. 6143
  • Achar, B.N., Lokesh, K.S., (2004) J. Organomet. Chem., 689, p. 3357
  • Fernández, D.A., Dicelio, L.E., Awruch, J., (1995) J. Heterocycl. Chem., 32, p. 519
  • Rodriguez, M.E., Strassert, C.A., Dicelio, L.E., Awruch, J., (2001) J. Heterocycl. Chem., 38, p. 387
  • Strassert, C.A., Rodriguez, M.E., Dicelio, L.E., Awruch, J., (2005) J. Porphyrins Phthalocyanines, 9, p. 361
  • (1999) Encyclopedia of Reagents for Organic Synthesis, 5, p. 3580. , Paquette, L. A., Ed.; John Wiley and Sons: Chichester
  • Arvela, R.K., Leadbeater, N.E., (2003) J. Org. Chem., 68, p. 9122
  • Burfield, D.R., Smithers, R.H., (1978) J. Org. Chem., 43, p. 3966
  • Duro, J.A., De La Torre, G., Barberá, J., Serrano, J.L., Torres, T., (1996) Chem. Mater., 8, p. 1061

Citas:

---------- APA ----------
Strassert, C.A., Dicelio, L.E. & Awruch, J. (2006) . Reduction of an amido zinc(II) phthalocyanine by diborane. Synthesis(5), 799-802.
http://dx.doi.org/10.1055/s-2006-926336
---------- CHICAGO ----------
Strassert, C.A., Dicelio, L.E., Awruch, J. "Reduction of an amido zinc(II) phthalocyanine by diborane" . Synthesis, no. 5 (2006) : 799-802.
http://dx.doi.org/10.1055/s-2006-926336
---------- MLA ----------
Strassert, C.A., Dicelio, L.E., Awruch, J. "Reduction of an amido zinc(II) phthalocyanine by diborane" . Synthesis, no. 5, 2006, pp. 799-802.
http://dx.doi.org/10.1055/s-2006-926336
---------- VANCOUVER ----------
Strassert, C.A., Dicelio, L.E., Awruch, J. Reduction of an amido zinc(II) phthalocyanine by diborane. Synthesis. 2006(5):799-802.
http://dx.doi.org/10.1055/s-2006-926336