Synthesis and functionalization of double picket fence porphyrins starting from 4,6-disubstituted pyrimidine-5-carbaldehydes

Journal of Organic Chemistry

Volumn 65, Issue 18, 2000, Pages 5882-5885

  Smeets, S ^a   Asokan, C V ^a   Motmans, F ^a   Dehaen, W ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYRIN DERIVATIVE; PYRIMIDINE 5 CARBALDEHYDE DERIVATIVE; UNCLASSIFIED DRUG;

CATALYSIS; NOTE; OXIDATION; OXYGEN AFFINITY; STEREOSPECIFICITY; SYNTHESIS;

EID: 0033824370     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0007938     Document Type: Note

References (37)

1. (a) Rose, E.; Quelquejeu, M.; Pandian, R. P.; Lecas-Nawrocka, A.; Vilar, A.; Ricart, G.; Collman, J. P.; Wang, Z. Straumanis, A. Polyhedron 2000, 19, 581-586.
2. (b) Rose, E.; Lecas, A.; Quelquejeu, M.; Kossanyi, A.; Boitrel, B. Coord. Chem. Rev. 1998, 178-180, 1407-1431.
3. (a) Collman, J. P.; Brauman, J. I.; Doxsee, K. M.; Halbert, T. R.; Hayes, S. E.; Suslick, K. S. J. Am. Chem. Soc. 1978, 100, 2761-2766
4. (b) Collman, J. P.; Gagne, R. R.; Halbert, T. R.; Manchon, J. C.; Reed, C. A. J. Am. Chem. Soc. 1973, 85, 7868-7870.
5. (a) Johnson, M. R.; Seok, W. K.; Ma, W.; Slebodnick, C.; Wilcoxen, K. M.; Ibers, J. A. J. Org. Chem. 1996, 61, 3298-3303.
6. (b) Slebodnick, C.; Fettinger, J. C.; Peterson, H. B.; Ibers, J. A. J. Am. Chem. Soc. 1996, 118, 3216-3224.
7. (c) Slebodnick, C.; Duval, M. L.; Ibers, J. A. Inorg. Chem. 1996, 35, 3607-3613.
8. (d) Slebodnick, C.; Ibers, J. A. J. Biol. Inorg. Chem. 1997, 2, 521-525.
9. (e) Johnson, M. R.; Soek, W. K.; Ibers, J. A. J. Am. Chem. Soc. 1991, 113, 3998-4000.
10. (f) Rose, E.; Boitrel, B.; Quelquejeu, M.; Kossanyi, A. Tetrahedron Lett. 1993, 34, 7267-7270.
11. (g) Hashimoto, T.; Dyer, R. L.; Crossley, M. J.; Baldwin, J. E.; Basolo, F. J. Am. Chem. Soc. 1982, 104, 2101-2109.
12. Rose, E.; Kossanyi, A.; Quelquejeu, M.; Soleilhavoup, M.; Duwavran, F.; Bernard N.; Lecas, A. J. Am. Chem. Soc. 1996, 118, 1567-1568.
13. (a) Suzuki, Y.; Nishide, H.; Tsuchida, E. Macromolecules 2000, 33, 2530-2534.
14. (b) Nishide, H.; Tsukahara, Y.; Tsuchida, E. J. Phys. Chem. B 1998, 102, 8766-8770.
15. (c) Nishide, H.; Suzuki, T.; Nakagawa, R.; Tsuchida, E. J. Am. Chem. Soc. 1994, 116, 4503-4504.
16. (d) Tsuchida, E.; Nishide, H.; Ohyanagi, M.; Okada, O. J. Phys. Chem. 1988, 92, 6461-6464.
17. (e) Nishide, H. Ohyanagi, M. Okada, O. Tsuchida, E. Macromolecules 1987, 20, 417-422.
18. (a) Naruta, Y.; Tani, F.; Ishihara, N.; Maruyama, K. J. Am. Chem. Soc. 1991, 113, 6865-6872.
19. (b) Naruta, Y.; Tani, F.; Maruyama, K. Tetrahedron: Asymmetry 1991, 2, 533-542.
20. (c) Naruta, Y.; Ishihara, N.; Tani, F.; Maruyama, K. Chem. Lett. 1991, 1933-1936.
21. (a) Matsu-ura, M.; Tani, F.; Nakayama, S.; Nakamura, N.; Naruta, Y. Angew. Chem., Int. Ed. 2000, 39, 1989-1991.
22. (b) Tani, F. Nakayama, S. Ichimura, M. Nakamura, N. Naruta, Y. Chem. Lett. 1999, 729-730.
23. (a) Tsuchida, E.; Komatsu, T.; Arai, K.; Nishide, H. J. Chem. Soc., Dalton Trans. 1993, 2465-2469.
24. (b) Tsuchida, E. Hasegawa, E.; Komatsu, T.; Nakata, T. Bull. Chem. Soc. Jpn. 1991, 64, 888-894.
25. (c) Komatsu, T.; Hasegawa, E.; Nishide, H.; Tsuchida E. Nakao, K.; Nishide, H. J. Chem. Soc., Chem. Commun. 1990, 66-68.
26. (d) Tsuchida, E.; Komatsu, T.; Hasegawa, E.; Nishide, H. J. Chem. Soc., Dalton Trans. 1990, 2713-2718.
27. (e) Tsuchida, E.; Hasegawa, E.; Komatsu, T.; Nakao, K.; Nishide, H. Chem. Lett. 1990, 1071-1074.
28. Rose, E.; Soleilhavoup, M.; Christ-Tommasino, L.; Moreau, G.; Collman, J. P.; Quelquejeu, M.; Straumanis, A. J. Org. Chem. 1998, 63, 2042-2044.
29. Drain, C. M.; Corden, B. B. Inorg. Chem. 1989, 28, 4374-4376.
30. Quintana, C. A.; Assink, R. A.; Shellnut, J. A. Inorg. Chem. 1989, 28, 3421-3245.
31. Longo, F. R.; Thorne, E. J.; Alder, A. D.; Dym, S. J. Heterocycl. Chem. 1975, 57, 1305-1309.
32. Lindsey, J. S. Wagner, R. W. J. Org. Chem. 1989, 54, 828-836.
33. Pozzi, G.; Banfi, S.; Manfredi, A.; Montanari, F.; Quici, S. Tetrahedron 1996, 36, 11879-11888.
34. Motmans, F.; Ceulemans, E.; Smeets S.; Dehaen, W. Tetrahedron Lett. 1999, 40, 7545-7548.
35. Klötzer W.; Herberz, M. Monatsh. Chem. 1966, 96, 1567-1572.
36. Lindsey, J. S.; Schreiman, I. C.; Hsu, H. C.; Kearney, P. C.; Marguerettaz, A. M. J. Org. Chem. 1987, 52, 827-836.
37. Lee C.-H., Lindsey, J. S. Tetrahedron 1994, 50, 11427-11440.