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Volumn 73, Issue 18, 2008, Pages 7353-7356

A new synthetic approach to N-arylquinolino[2,3,4-at]porphyrins from β-arylaminoporphyrins

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION; AMINATION; AMINES; CHEMICAL REACTIONS; NICKEL; NICKEL COMPOUNDS; PALLADIUM;

EID: 52449118519     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800975c     Document Type: Article
Times cited : (46)

References (28)
  • 1
    • 0003641908 scopus 로고    scopus 로고
    • Kadish, K. M, Smith, K. M, Guillard, R, Eds, Academic Press: San Diego
    • The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guillard, R., Eds.; Academic Press: San Diego, 2000; Vol. 6.
    • (2000) The Porphyrin Handbook , vol.6
  • 13
    • 33748777687 scopus 로고    scopus 로고
    • Tomé, J. P. C.; Pereira, A. M; V, M.; Alonso, C. M. A.; Neves, M. G. P. M. S.; Tomé, A. C.; Silva, A. M. S.; Cavaleiro, J. A. S.; Martínez-Díaz, M. V.; Torres, T.; Rahman, G. M. A.; Ramey, J.; Guldi, D. M. Eur. J. Org. Chem. 2006, 257.
    • Tomé, J. P. C.; Pereira, A. M; V, M.; Alonso, C. M. A.; Neves, M. G. P. M. S.; Tomé, A. C.; Silva, A. M. S.; Cavaleiro, J. A. S.; Martínez-Díaz, M. V.; Torres, T.; Rahman, G. M. A.; Ramey, J.; Guldi, D. M. Eur. J. Org. Chem. 2006, 257.
  • 14
    • 33748578357 scopus 로고    scopus 로고
    • For a recent review on this subject, see: a
    • For a recent review on this subject, see: (a) Fox, S.; Boyle, R. W. Tetrahedron 2006, 62, 10039.
    • (2006) Tetrahedron , vol.62 , pp. 10039
    • Fox, S.1    Boyle, R.W.2
  • 19
    • 84986483914 scopus 로고    scopus 로고
    • Nitrobenzene is frequently used as a dehydrogenating agent in porphyrin synthesis: Gonsalves, A. M.; Rocha, d'A.; Varejão, J. M. T. B.; Pereira, M. M J. Heterocycl. Chem. 1991, 28, 635.
    • Nitrobenzene is frequently used as a dehydrogenating agent in porphyrin synthesis: Gonsalves, A. M.; Rocha, d'A.; Varejão, J. M. T. B.; Pereira, M. M J. Heterocycl. Chem. 1991, 28, 635.
  • 20
    • 34247476215 scopus 로고    scopus 로고
    • Compound 4 has already been used in the preparation of a 4-(porphyrin-2-ylamino)phthalonitrile via palladium-catalyzed amination: Soares, A. R. M.; Martínez-Díaz, M. V.; Bruckner, A.; Pereira, A. M. V. M.; Tomé, J. P. C.; Alonso, C. M. A.; Faustino, M. A. F.; Neves, M. G. P. M. S.; Tomé, A. C.; Silva, A. M. S.; Cavaleiro, J. A. S.; Torres, T.; Guldi, D. M. Org. Lett. 2007, 9, 1557.
    • Compound 4 has already been used in the preparation of a 4-(porphyrin-2-ylamino)phthalonitrile via palladium-catalyzed amination: Soares, A. R. M.; Martínez-Díaz, M. V.; Bruckner, A.; Pereira, A. M. V. M.; Tomé, J. P. C.; Alonso, C. M. A.; Faustino, M. A. F.; Neves, M. G. P. M. S.; Tomé, A. C.; Silva, A. M. S.; Cavaleiro, J. A. S.; Torres, T.; Guldi, D. M. Org. Lett. 2007, 9, 1557.
  • 21
    • 0042381716 scopus 로고    scopus 로고
    • There are also some reports regarding the synthesis of aminoporphyrins via palladium-catalyzed amination of β-bromo, meso-bromo, and meso-halogenophenylporphyrins with amines and amides: (a) Takanami, T, Hayashi, M, Hino, F, Suda, K. Tetrahedron Lett. 2003, 44, 7353
    • There are also some reports regarding the synthesis of aminoporphyrins via palladium-catalyzed amination of β-bromo, meso-bromo-, and meso-halogenophenylporphyrins with amines and amides: (a) Takanami, T.; Hayashi, M.; Hino, F.; Suda, K. Tetrahedron Lett. 2003, 44, 7353.
  • 28
    • 52449120278 scopus 로고    scopus 로고
    • int = 0.0819). Final R1 = 0.0455 [I > 2σ (I)] and wR2 = 0.1151 (all data). CCDC 642548. See the Supporting Information for further details on the crystal solution and refinement.
    • int = 0.0819). Final R1 = 0.0455 [I > 2σ (I)] and wR2 = 0.1151 (all data). CCDC 642548. See the Supporting Information for further details on the crystal solution and refinement.


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