Stepwise synthesis of substituted dicyanotriazolehemiporphyrazines. A regioselective approach to unsymmetrically substituted hemiporphyrazines

Journal of Organic Chemistry

Volumn 61, Issue 18, 1996, Pages 6446-6449

  De La Torre, Gema ^a   Torres, Tomás ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND; PHTHALOCYANINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SPECTROPHOTOMETRY; TECHNIQUE;

EID: 0029789725     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960704k     Document Type: Article

References (30)

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14. See, for example: Sastre, A.; Torres, T.; Díaz-García, M. A.; Agulló-López, F.; Dhenaut, C.; Brasselet, S.; Ledoux, I.; Zyss, J. J. Am. Chem. Soc. 1996, 118, 2746, and literature cited therein.
15. The regioselective preparation of related unsymmetrically substituted phthlocyanines is also difficult. See, for example: (a) Kobayashi, N; Kondo, R.; Nakajima, S.; Osa, T. J. Am. Chem. Soc. 1990, 112, 9640. (b) Weitemeyer, A.; Kliesch, H.; Wörhle, D. J. Org. Chem. 1995, 60, 4900. (c) Sastre, A.; Torres, T.; Hanack, M. Tetrahedron. Lett. 1995, 36, 8501. (d) Leznoff, C. C. In International Chemical Congress of Pacific Basin Societies, Honolulu, HI, 1995.
16. The regioselective preparation of related unsymmetrically substituted phthlocyanines is also difficult. See, for example: (a) Kobayashi, N; Kondo, R.; Nakajima, S.; Osa, T. J. Am. Chem. Soc. 1990, 112, 9640. (b) Weitemeyer, A.; Kliesch, H.; Wörhle, D. J. Org. Chem. 1995, 60, 4900. (c) Sastre, A.; Torres, T.; Hanack, M. Tetrahedron. Lett. 1995, 36, 8501. (d) Leznoff, C. C. In International Chemical Congress of Pacific Basin Societies, Honolulu, HI, 1995.
17. The regioselective preparation of related unsymmetrically substituted phthlocyanines is also difficult. See, for example: (a) Kobayashi, N; Kondo, R.; Nakajima, S.; Osa, T. J. Am. Chem. Soc. 1990, 112, 9640. (b) Weitemeyer, A.; Kliesch, H.; Wörhle, D. J. Org. Chem. 1995, 60, 4900. (c) Sastre, A.; Torres, T.; Hanack, M. Tetrahedron. Lett. 1995, 36, 8501. (d) Leznoff, C. C. In International Chemical Congress of Pacific Basin Societies, Honolulu, HI, 1995.
18. The regioselective preparation of related unsymmetrically substituted phthlocyanines is also difficult. See, for example: (a) Kobayashi, N; Kondo, R.; Nakajima, S.; Osa, T. J. Am. Chem. Soc. 1990, 112, 9640. (b) Weitemeyer, A.; Kliesch, H.; Wörhle, D. J. Org. Chem. 1995, 60, 4900. (c) Sastre, A.; Torres, T.; Hanack, M. Tetrahedron. Lett. 1995, 36, 8501. (d) Leznoff, C. C. In International Chemical Congress of Pacific Basin Societies, Honolulu, HI, 1995.
19. Maya, E.; Vázquez, P.; Torres, T. Unpublished results.
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22. Phthalocyanines having two o-cyano groups have been used as starting materials for the preparation of binuclear phthalocyanine systems: Kobayashi, N.; Higashi, Y.; Osa, T. J. Chem. Soc., Chem. Commun. 1994, 1785.
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24. Three-unit compounds related to 4 having two pyridine units instead of the triazole ones have been described; see, for example: (a) Siegl, W. O. J. Org. Chem. 1977, 42, 1872. (b) Siegl, W. O. J. Heterocycl. Chem. 1981, 78, 1613.
25. Three-unit compounds related to 4 having two pyridine units instead of the triazole ones have been described; see, for example: (a) Siegl, W. O. J. Org. Chem. 1977, 42, 1872. (b) Siegl, W. O. J. Heterocycl. Chem. 1981, 78, 1613.
26. Rodríguez-Morgade, S.; Torres, T. Inorg. Chim. Acta 1995, 230, 153.
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29. (c) For 5-nitro-1,3-diiminoisoindoline (2d): Young, J. G.; Onyebuagu, W. J. Org. Chem. 1990, 55, 2155.
30. 1H NMR spectra of structurally related aromatic phthalocyanines at very high field (ca. -3 to -5 ppm).