A new synthesis of benzoporphyrins using 4,7-dihydro-4,7-ethano-2H-isoindole as a synthon of isoindole

Chemical Communications

Volumn , Issue 16, 1998, Pages 1661-1662

  Ito, Satoshi ^a   Murashima, Takashi ^a   Uno, Hidemitsu ^a   Ono, Noboru ^a  

^a EHIME UNIVERSITY   (Japan)

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EID: 0000640243     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a803656j     Document Type: Article

References (21)

1. N. Ono, H. Hironaga, K. Simidzu, K. Ono and T. Ogawa, J. Chem. Soc., Chem. Commun., 1994, 1019;
2. N. Ono, C. Tsukamura, Y. Nomura, H. Hironaga, T. Murashima and T. Ogawa, Adv. Mater., 9, 1997, 149.
3. Polypyrroles fused with aromatic rings have been little studied, while the corresponding polythiophenes have been well-studied, see F. Wudl, M. Kobayashi and A. J. Heager, J. Org. Chem., 1984, 49, 3382;
4. M. Hanack, U. Schmid, S. Echingerr, F. Teichert and J. Heiber, Syntheis, 1993, 634.
5. N. Ono, H. Hironaga, K. Ono, S. Kaneko, T. Murashima, T. Ueda, C. Tsukamura and T. Ogawa, J. Chem. Soc., Perkin Trans, 1, 1996, 417;
6. T. D. Lash and B. H. Novak, Angew. Chem., Int. Ed. Engl, 1995, 34, 683;
7. P. Chandrasekar and T. D. Lash, Tetrahedron Lett., 1996, 28, 4873 and references cited therein.
8. R. Bonnett and R. C. Brown, J. Chem. Soc., Chem. Commun., 1972, 393;
9. R. Bonnett and S. A. North, in Advances in heterocyclic chemistry, ed. A. R. Katritzky and A. J. Boulton, Academic Press, New York, 1981, vol. 29, pp. 341-399;
10. R. Kreher, N. Kohl and G. Use, Angew. Chem., Int. Ed. Engl, 1982, 21, 621;
11. M. Lee, H. Morimoto and K. Kanematsu, J. Chem. Soc., Chem. Commun., 1994, 1535.
12. S. Ito, T. Murashima and N. Ono, J. Chem. Soc., Perkin Trans, 1, 1997, 3161.
13. The retro-Diels-Alder reaction of 1 or 2 takes place at 200-230 °C, the bridged moiety of 1 and 2 being stable during de-ethoxycarbonylation of 1 at 170 °C. The formation of isoindoles from 1 or 2 by heating was monitored via NMR spectroscopy.
14. K. M. Smith, Porphyrins and Metalloporphyrins, Elsevier, Amsterdam, 1975.
15. Existing methods for benzoporphyrin synthesis are summarized in R. Bonnett and K. A. McManus, J. Chem. Soc., Perkin Trans, 1, 1996, 2461;
16. for a recent synthesis of benzoporphyrins, see M. G. H. Vicente, A. C. Tome, A. Walter and J. A. S. Cavaleiro, Tetrahedron Lett., 1997, 38, 3639 and references cited therein.
17. T. D. Lash, Chem. Eur. J., 1996, 2, 1197;
18. A. Boudif and M. Momenteau, J. Chem. Soc., Perkin Trans, 1, 1996, 1235;
19. L. T. Nguyen, M. O. Senge and K. M. Smith, J. Org. Chem., 1996, 61, 998 and references cited therein.
20. P. S. Clezy and A. H. Mirza, Aust. J. Chem., 1982, 35, 197;
21. T. D. Lash, Energy Fuels, 1993, 7, 166.