meso-Arylporphyrins as dienophiles in Diels–Alder reactions: a novel approach to the synthesis of chlorins, bacteriochlorins and naphthoporphyrins

Abstract

meso-Arylporphyrins participate, as dienophiles, in Diels–Alder reactions with o-benzoquinodimethane to yield novel chlorins, bacteriochlorins and naphtho[2,3-b]porphyrins.

References

1. R. Bonnet, Chem. Soc. Rev., 1995, 24, 19.
2. S. Wan, J. A. Parrish, R. R. Anderson and M. Madden, Photochem. Photobiol., 1991, 34, 679.
3. R. K. DiNello and D. Dolphin, J. Org. Chem., 1980, 45, 5196; A. R. Morgan, V. S. Pangka and D. Dolphin, J. Chem. Soc., Chem. Commun., 1984, 1047; V. S. Pangka, A. R. Morgan and D. Dolphin, J. Org. Chem., 1986, 51, 1094; P. Yong-Hin, T. P. Wijesekera and D. Dolphin, Tetrahedron Lett., 1989, 30, 6135; A. R. Morgan and D. H. Kohli, Tetrahedron Lett., 1995, 36, 7603; M. A. F. Faustino, M. G. P. M. S. Neves, M. G. H. Vicente, A. M. S. Silva and J. A. S. Cavaleiro, Tetrahedron Lett., 1996, 37, 3569.
4. (a) H. J. Callot, A. W. Johnson and A. Sweeney, J. Chem. Soc., Perkin Trans. 1, 1973, 1424; (b) J. A. S. Cavaleiro, A. H. Jackson, M. G. P. M. S. Neves and K. R. N. Rao, J. Chem. Soc., Chem. Commun., 1985, 776; (c) P. Yong-Hin, T. P. Wijesekera and D. Dolphin, Tetrahedron Lett., 1991, 32, 2875; (d) R. K. Pandey, F.-Y. Shiau, K. Ramachandran, T. J. Dougherty and K. M. Smith, J. Chem. Soc., Perkin Trans. 1, 1992, 1377.
5. H. J. Callot, Tetrahedron Lett., 1972, 1011.
6. H. Scheer and H. Inhoffen, Hydroporphyrins: Reactivity, Spectroscopy, and Hydroporphyrin Analogues, in The Porphyrins, ed. D. Dolphin, Academic Press, New York, 1978, vol. 2, part B, p. 77.
7. The synthesis and characterisation of meso-unsubstituted naphtho[1,2-b]porphyrins and dinaphthoporphyrins was recently reported: T. D. Lash and T. D. Roper, Terahedron Lett., 1994, 35, 7715; D. T. Lash and C. P. Denny, Tetrahedron, 1995, 51, 59; T. D. Lash, C. Wijesinghe, A. T. Osuma and J. R. Patel, Tetrahedron Lett., 1997, 38, 2031.