A new synthesis of pyrroles and porphyrins fused with aromatic rings

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 5, 1996, Pages 417-423

  Ono, Noboru ^a   Hironaga, Hideo ^a   Ono, Kazuo ^a   Kaneko, Syunichi ^a   Murashima, Takashi ^a   Ueda, Takahiro ^a   Tsukamura, Chikanori ^a   Ogawa, Takuji ^a  

^a EHIME UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005372299     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960000417     Document Type: Article

References (33)

1. M. Hanack and M. Lang, Adv. Mater, 1994, 6, 819;
2. B. M. Hoffman and J. A. Ibers, Acc. Chem. Res., 1983, 16, 15.
3. C. L. Honeybourne, J. Chem. Soc., Chem. Commun., 1982, 744.
4. R. Bonnett, Chem. Soc. Rev., 1995, 24, 19 and references therein.
5. P. Yon-Hin, T. P. Wijesekera and D. Dolphin, Tetrahedron Lett., 1989, 30, 6135.
6. R. Bonnett and K. A. McManus, J. Chem. Soc., Chem. Commun., 1994, 1129.
7. T. D. Lash and C. P. Denny, Tetrahedron, 1995, 51, 166.
8. T. D. Lash and T. J. Roper, Tetrahedron Lett., 1994, 35, 7715.
9. T. D. Lash and B. H. Novak, Angew. Chem., Int. Ed. Engl., 1995, 34, 683.
10. R. B. M. Koehorst, J. F. Kleibeuker, T. J. Schaafsma, D. A. de Bie, B. Geurtsen, R. N. Henrie and H. C. van der Plas, J. Chem. Soc., Perkin Trans. 2, 1981, 1005.
11. M. Rein and M. Hanack, Chem. Ber., 1988, 121, 1601.
12. R. J. Sundberg, Comprehensive Heterocyclic Compounds, ed. A. R. Katritzky and C. W. Rees, Pergamon Press, London, 1984, vol. 1, p. 156.
13. N. Ono, H. Hironaga, K. Simizu, K. Ono, K. Kuwano and T. Ogawa, J. Chem. Soc., Chem. Commun., 1994, 1019;
14. T. D. Lash, B. H. Novak and Y. Lin, Tetrahedron Lett., 1994, 35, 2493.
15. D. H. R. Barton, J. Kervagoret and S. Z. Zard, Tetrahedron, 1990, 46, 7587.
16. S. Jew, H. Kim, Y. Cho and C. Cook, Chem. Lett., 1986, 747.
17. L. T. Nguyen, M. O. Senge and K. M. Smith, Tetrahedron Lett., 1994, 35, 7581;
18. A. Boudif and M. Momenteau, J. Chem. Soc., Chem. Commun., 1994, 2069.
19. N. Ono, A. Kamimura and A. Kaji, J. Org. Chem., 1988, 53, 251.
20. F. Terrier, Nucleophilic Aromatic Displacement: The Influence of the Nitro Group, VCH, New York, 1981.
21. N. Ono, H. Kawamura, M. Bougauchi and K. Maruyama, Tetrahedron, 1990, 46, 7483.
22. J. Tang and J. G. Verkade, J. Org. Chem., 1994, 59, 7793.
23. D. Mauzerall, J. Am. Chem. Soc., 1960, 82, 2601;
24. K. M. Smith and F. Eivazi, J. Org. Chem., 1979, 44, 2591.
25. N. Ono and K. Maruyama, Chem. Lett., 1989, 1237.
26. C. Pichon and A. I. Scott, Tetrahedron Lett., 1994, 35, 4497.
27. M. Onaka, T. Shinoda, Y. Izumi and E. Nolen, Chem Lett., 1993, 117.
28. P. G. Sammes and G. Yahioglu, Chem. Soc. Rev., 1994, 23, 327.
29. A preliminary account was presented at the 6th International Kyoto conference on New Aspect of Organic Chemistry, 1994, November, Abstract: N. Ono, T. Kaneko, T. Murashima, C. Tsukamura and T. Ogawa, PP 225. Independently, Lash has reported the preparation of 4g by a similar procedure, see, ref. 8.
30. T. S. Cantrell and H. Shechter, J. Org. Chem., 1968, 33, 114.
31. P. M. G. Babin and M. J. S. Dewar, J. Chem. Soc., 1955, 4477.
32. 4 at 130°C.
33. 'Porphyrins and Metalloporphyrins', ed. K. M. Smith, Elsevier, Amsterdam, 1975.