Selective synthesis of meso-naphthylporphyrins

Journal of Organic Chemistry

Volumn 67, Issue 21, 2002, Pages 7457-7464

  Cammidge, Andrew N ^a   Öztürk, Orhan ^a  

^a UNIVERSITY OF EAST ANGLIA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ATROPISOMERS;

ALDEHYDES; CONDENSATION; DERIVATIVES; PORPHYRINS;

SYNTHESIS (CHEMICAL);

(PENTAFLUOROPHENYL)DIPYRROMETHANE; ALDEHYDE DERIVATIVE; ALPHA,ALPHA 5,15 BISNAPHTHYLPORPHYRIN DERIVATIVE; BENZALDEHYDE; BIS(DIPYRROMETHANE) DERIVATIVE; BISNAPHTHALDEHYDE; NAPHTHYL GROUP; PHENYLDIPYRROMETHANE; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; POLYMERIZATION; SYNTHESIS;

INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NAPHTHOLS; PORPHYRINS; STEREOISOMERISM;

EID: 0037131251     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0260488     Document Type: Article

References (35)

1. (a) Fischer, H.; Zeile, K. Liebigs Ann. Chem. 1929, 468, 98.
2. (b) Fischer, H.; Orth, H. Die Chemie des Pyrrols; Akademische Verlag: Leipzig, 1934; Vol 1.
3. (c) Fischer, H.; Orth, H. Die Chemie des Pyrrols; Akademische Verlag: Leipzig, 1937; Vol 2, Part 1.
4. (d) H. Fischer, H.; Stern, A. Die Chemie des Pyrrols; Akademische Verlag: Leipzig, 1940; Vol 2, Part 2.
5. Kadish, K. M.; Smith, K. M.; Guilard, R. (Eds.) The Porphyrin Handbook; Academic Press: Boston, 2000; Vols. 1-10.
6. meso-Naphth-1-ylporphyrins bearing hydroxyl substituents at the 2- and/or 7-positions have been reported: (a) Mizutani, T.; Kurahashi, T.; Murakami, T.; Matsumi N.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 8991. (b) Hayashi, T.; Miyahara, T.; Koide, N.; Kato, Y.; Masuda, H.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 7281. (c) Mizutani, T.; Murakami, T.; Ogoshi, H. Tetrahedron Lett. 1996, 37, 5369. (d) Hayashi, T.; Miyahara, T.; Aoyama, Y.; Nonoguchi, M.; Ogoshi, H. Chem. Lett. 1994, 1749. (e) Hayashi, T.; Miyahara, T.; Hashizumi, N. Ogoshi, H. J. Am. Chem. Soc. 1993, 115, 2049. (f) Hayashi, T.; Miyahara, T.; Aoyama, Y.; Ogoshi, H. Pure Appl. Chem. 1994, 66, 797.
7. meso-Naphth-1-ylporphyrins bearing hydroxyl substituents at the 2- and/or 7-positions have been reported: (a) Mizutani, T.; Kurahashi, T.; Murakami, T.; Matsumi N.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 8991. (b) Hayashi, T.; Miyahara, T.; Koide, N.; Kato, Y.; Masuda, H.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 7281. (c) Mizutani, T.; Murakami, T.; Ogoshi, H. Tetrahedron Lett. 1996, 37, 5369. (d) Hayashi, T.; Miyahara, T.; Aoyama, Y.; Nonoguchi, M.; Ogoshi, H. Chem. Lett. 1994, 1749. (e) Hayashi, T.; Miyahara, T.; Hashizumi, N. Ogoshi, H. J. Am. Chem. Soc. 1993, 115, 2049. (f) Hayashi, T.; Miyahara, T.; Aoyama, Y.; Ogoshi, H. Pure Appl. Chem. 1994, 66, 797.
8. meso-Naphth-1-ylporphyrins bearing hydroxyl substituents at the 2- and/or 7-positions have been reported: (a) Mizutani, T.; Kurahashi, T.; Murakami, T.; Matsumi N.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 8991. (b) Hayashi, T.; Miyahara, T.; Koide, N.; Kato, Y.; Masuda, H.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 7281. (c) Mizutani, T.; Murakami, T.; Ogoshi, H. Tetrahedron Lett. 1996, 37, 5369. (d) Hayashi, T.; Miyahara, T.; Aoyama, Y.; Nonoguchi, M.; Ogoshi, H. Chem. Lett. 1994, 1749. (e) Hayashi, T.; Miyahara, T.; Hashizumi, N. Ogoshi, H. J. Am. Chem. Soc. 1993, 115, 2049. (f) Hayashi, T.; Miyahara, T.; Aoyama, Y.; Ogoshi, H. Pure Appl. Chem. 1994, 66, 797.
9. meso-Naphth-1-ylporphyrins bearing hydroxyl substituents at the 2- and/or 7-positions have been reported: (a) Mizutani, T.; Kurahashi, T.; Murakami, T.; Matsumi N.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 8991. (b) Hayashi, T.; Miyahara, T.; Koide, N.; Kato, Y.; Masuda, H.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 7281. (c) Mizutani, T.; Murakami, T.; Ogoshi, H. Tetrahedron Lett. 1996, 37, 5369. (d) Hayashi, T.; Miyahara, T.; Aoyama, Y.; Nonoguchi, M.; Ogoshi, H. Chem. Lett. 1994, 1749. (e) Hayashi, T.; Miyahara, T.; Hashizumi, N. Ogoshi, H. J. Am. Chem. Soc. 1993, 115, 2049. (f) Hayashi, T.; Miyahara, T.; Aoyama, Y.; Ogoshi, H. Pure Appl. Chem. 1994, 66, 797.
10. meso-Naphth-1-ylporphyrins bearing hydroxyl substituents at the 2- and/or 7-positions have been reported: (a) Mizutani, T.; Kurahashi, T.; Murakami, T.; Matsumi N.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 8991. (b) Hayashi, T.; Miyahara, T.; Koide, N.; Kato, Y.; Masuda, H.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 7281. (c) Mizutani, T.; Murakami, T.; Ogoshi, H. Tetrahedron Lett. 1996, 37, 5369. (d) Hayashi, T.; Miyahara, T.; Aoyama, Y.; Nonoguchi, M.; Ogoshi, H. Chem. Lett. 1994, 1749. (e) Hayashi, T.; Miyahara, T.; Hashizumi, N. Ogoshi, H. J. Am. Chem. Soc. 1993, 115, 2049. (f) Hayashi, T.; Miyahara, T.; Aoyama, Y.; Ogoshi, H. Pure Appl. Chem. 1994, 66, 797.
11. meso-Naphth-1-ylporphyrins bearing hydroxyl substituents at the 2- and/or 7-positions have been reported: (a) Mizutani, T.; Kurahashi, T.; Murakami, T.; Matsumi N.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 8991. (b) Hayashi, T.; Miyahara, T.; Koide, N.; Kato, Y.; Masuda, H.; Ogoshi, H. J. Am. Chem. Soc. 1997, 119, 7281. (c) Mizutani, T.; Murakami, T.; Ogoshi, H. Tetrahedron Lett. 1996, 37, 5369. (d) Hayashi, T.; Miyahara, T.; Aoyama, Y.; Nonoguchi, M.; Ogoshi, H. Chem. Lett. 1994, 1749. (e) Hayashi, T.; Miyahara, T.; Hashizumi, N. Ogoshi, H. J. Am. Chem. Soc. 1993, 115, 2049. (f) Hayashi, T.; Miyahara, T.; Aoyama, Y.; Ogoshi, H. Pure Appl. Chem. 1994, 66, 797.
12. An elegant approach to naphth-1-ylporphyrins has recently been reported: (a) Harmjanz, M.; Scott, M. J. Chem. Commun. 2000, 397. (b) Harmjanz, M.; Gill, H. S.; Scott, M. J. J. Org. Chem. 2001, 66, 5374.
13. An elegant approach to naphth-1-ylporphyrins has recently been reported: (a) Harmjanz, M.; Scott, M. J. Chem. Commun. 2000, 397. (b) Harmjanz, M.; Gill, H. S.; Scott, M. J. J. Org. Chem. 2001, 66, 5374.
14. Gottwald, L. K.; Ullman, E. F. Tetrahedron Lett. 1969, 3071.
15. (a) Adler, A. D.; Longo, R. F.; Finarelli, J. D.; Goldmacher, J.; Assour, J.; Korsakoff, L. J. Org. Chem. 1967, 32, 476.
16. (b) Lindsey, J. S.; Schreiman, I. C.; Hsu, H. C.; Kearney, P. C.; Marguerettaz. A. M. J. Org. Chem. 1987, 52, 827.
17. Hayashi, T.; Asai, T.; Hokazono, H.; Ogoshi, H. J. Am. Chem. Soc. 1993, 115, 12210.
18. (a) Packer, R. J.; Smith, D. C. C. J. Chem. Soc. (C) 1976, 2194.
19. (b) Elliger, C. A. Org. Prep. Preced. Int. 1985, 17, 419.
20. Lacy, P. H.; Smith, D. C. C. J. Chem. Soc., Perkin Trans. 11975, 419.
21. Lindsey, J. S.; MacCrum, K. A.; Tyhonas, J. S.; Chuang, Y.-Y. J. Org. Chem. 1994, 59, 579.
22. Wang, Q. M.; Bruce, D. W. Tetrahedron Lett. 1996, 37, 7641.
23. (a) Arsenault, G. P.; Bullock, E.; MacDonald, S. F. J. Am. Chem. Soc. 1960, 82, 4384.
24. (b) Cavaliero, J. A. S.; Rocha Gonslaves, A. M. d'A.; Kenner, G. W.; Smith, K. M. J. Chem. Soc., Perkin Trans. 1 1974, 1771.
25. Cammidge, A. N.; Öztürk, O. Tetrahedron Lett. 2001, 42, 355.
26. (a) Wallace, D. M.; Leung, S.; Senge, M. O.; Smith, K. M. J. Org. Chem. 1993, 58, 7245.
27. (b) Litter, B. J.; Ciringh, Y.; Lindsey, J. S. J. Org. Chem. 1999, 64, 2864.
28. (c) Geier, G. R., III; Lindsey, J. S. J. Chem. Soc., Perkin Trans. 2 2001, 677.
29. (d) Geier, G. R., III; Lindsey, J. S. J. Chem. Soc., Perkin Trans. 2 2001, 687.
30. (e) Geier, G. R., III; Litter, B. J.; Lindsey, J. S. J. Chem. Soc., Perkin Trans. 2 2001, 701.
31. (f) Geier, G. R., III; Litter, B. J.; Lindsey, J. S. J. Chem. Soc., Perkin Trans. 2 2001, 712.
32. Foxton, S. P.; Lindsay Smith, J. R.; O'Brien, P.; Reginato, G. J. Chem. Soc., Perkin Trans. 2 2001, 1145.
33. Setsune, J.; Hashimoto, M.; Shiozawa, K.; Hayakawa, J.; Ochi, T.; Masuda, R. Tetrahedron 1998, 54, 1407.
34. (a) Berry, D.; Smith, D. C. C. J. Chem. Soc., Perkin Trans. 1 1972, 699.
35. (b) Kleinfelter, D. C.; Chen, P. H. J. Org. Chem. 1969, 34, 1741.