3-Cyclobutenyl-1,2-dione-substituted porphyrins. A general and efficient entry to porphyrin-quinone and quinone-porphyrin-quinone architectures

Journal of Organic Chemistry

Volumn 65, Issue 6, 2000, Pages 1650-1664

  Shi, Xianglin ^a   Amin, Sk Rasidul ^a   Liebeskind, Lanny S ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 (2 ISOPROPOXYCYCLOBUTENE 3,4 DIONYL) 10,20 DIPHENYLPORPHYRIN; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DRUG BINDING; DRUG STRUCTURE; PORPHYRIN METABOLISM; STRUCTURE ANALYSIS; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; CYCLOBUTANES; ELECTROSTATICS; HEAT; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; PORPHYRINS; QUINONES; SPECTROPHOTOMETRY;

EID: 0034708567     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9912799     Document Type: Article

References (69)

1. Bonnett, R. Chem. Soc. Rev. 1995, 19-33.
2. Frank, B.; Nonn, A. Angew. Chem. Int. Ed. Engl. 1995, 34, 1795.
3. Malik, Z.; Ladan, H.; Nitzan, Y.; Smetana, Z. Proc. SPIE-Int. Soc. Opt. Eng. 1994, 2078, 305-12.
4. Li, H.; Fedorova, O. S.; Grachev, A. N.; Trumble, W. R.; Bohach, G. A.; Czuchajowski, L. Biochim. Biophys. Acta 1997, 1354, 252-260.
5. Malik, Z.; Hanania, J.; Nitzan, Y. J. Photochem. Photobiol., B 1990, 5, 281-93.
6. Song, R.; Witvrouw, M.; Schols, D.; Robert, A.; Balzarini, J.; De Clercq, E.; Bernadou, J.; Meunier, B. Antiviral Chem. Chemother. 1997, 8, 85-97.
7. LeCours, S. M.; DiMagno, S. G. F.; Therien, M. J. J. Am. Chem. Soc. 1996, 118, 1854.
8. Kandasamy, S.; Shetty, S. J.; Puntambekar, P. N.; Srivastava, T. S.; Kundu, T.; Singh, B. P. J. Porphyrins Phthalocyanines 1999, 3, 81-86.
9. Milgrom, L. R. Porphyrins and the Electronics Revolution. Porphyrins for the Future; Oxford University Press: Oxford, 1997; Chapter 7, Section 5, pp 191-243.
10. Benniston, A. C.; Mackie, P. R.; Harriman, A. Angew. Chem. 1998, 37, 354.
11. Osuka, A.; Mataga, N.; Okada, T. Pure Appl. Chem. 1987, 69, 797.
12. Harriman, A.; Sauvage, J.-P. Chem. Soc. Rev. 1996, 41-48.
13. Kurreck, H.; Huber, M. Angew. Chem. Int. Ed. Engl. 1995, 34, 849-866.
14. Waseilewski, R. Chem. Rev. 1992, 92, 435.
15. Hyslop, A. G.; Kellett, M. A.; Therien, M. J. J. Am. Chem. Soc. 1998, 120, 12676.
16. DiMagno, S. G.; Lin, V. S. Y.; Therien, M. J. J. Org. Chem. 1993, 58, 8, 5983-5993.
17. DiMagno, S. G.; Lin, V. S.-Y.; Therien, M. J. J. Am. Chem. Soc. 1993, 115, 2513-2515.
18. Belcher, W. J.; Burrell, A. K.; Wild, K. Y. Tetrahedron 1999, 55, 2401 and references therein.
19. Collman, J. P.; Wang, Z. Chemtracts-Org. Chem. 1999, 12, 229-263.
20. Piotrowiak, P. Chem. Soc. Rev. 1999, 28, 143-150.
21. Yang, S.; Seth, J.; Strachan, J.-P.; Gentenann, S.; Kim, D.; Holten, D.; Lindsey, J. S.; Bocian, D. F. J. Porphyrins Phthalocyanines 1999, 3, 117-147.
22. Moore, H. W.; Yerxa, B. R. In Synthetic Utility of Cyclobutenediones; Halton, B., Ed.; JAI Press: Greenwich, CT, 1995; Vol. 4, pp 81-162.
23. Liebeskind, L. S. Tetrahedron Symp. Print 1989, 45, 3053-3060.
24. Koo, S.; Liebeskind, L. S. J. Am. Chem. Soc. 1995, 117, 3389-3404.
25. Sun, L.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 12473.
26. Paquette, L. A.; Doussot, P. Res. Chem. Intermed. 1996, 22, 767-780.
27. Ohno, M.; Yamamoto, Y.; Eguchi, S. Synlett 1998, 1167.
28. Voet, D.; Voet, J. G. Biochemistry, 2nd ed.; John Wiley & Sons: New York, 1995.
29. Senge, M. O.; Speck, M.; Wiehe, A.; Dieks, H.; Aguirre, S.; Kurreck, H. Photochem. Photobiol. 1999, 70, 206-216.
30. Gust, D. E.; Moore, T. A. In Photosynthetic Model Systems; Mattay, J., Ed.; Springer-Verlag: Berlin, 1991; Vol. 159, pp 105-151.
31. Mehta, G.; Muthusamy, S.; Maiya, B. G.; Arounaguiri, S. Tetrahedron. Lett. 1997, 38, 7125-7128.
32. Grennberg, H.; Faizon, S.; Bäckvall, J. E. Angew. Chem. Int. Ed. Engl. 1993, 32, 263-264.
33. Chan, C.-S.; Tse, A. K.-S.; Chan, K. S. J. Org. Chem. 1994, 59, 6084-6089.
34. Chan, C.-S.; Mak, C. C.; Chan, K. S. Tetrahedron Lett. 1993, 34, 5125-5126.
35. Manka, J. S.; Lawrence, D. S. Tetrahedron Lett. 1989, 30, 7341-7344.
36. Lin, V. S.-Y.; DiMagno, S. G.; Therien, M. J. Science 1994, 264, 1105-1111.
37. Boyle, R. W.; Johnson, C. K.; Dolphin, D. J. Chem. Soc., Chem. Commun. 1995, 527.
38. Zhou, X.; Chan, K. S. J. Chem. Soc., Chem. Commun. 1994, 2493-2494.
39. Chan, K. S.; Chan, C. S. Synth. Commun. 1993, 23, 1489-1497.
40. Chan, K. S.; Zhou, X.; Au, M. T.; Tam, C. Y. Tetrahedron 1995, 51, 3129-3136.
41. Wagner, R. W.; Johnson, T. E.; Li, F.; Lindsey, J. S. J. Org. Chem. 1995, 60, 5266-5273.
42. Lindsey, J. S.; Wagner, R. W.; Johnson, T. E. J. Am. Chem. Soc. 1996, 118, 11166.
43. Lindsey, J. S.; Prathapan, S.; Johnson, T. E.; Wagner, R. W. Tetrahedron 1994, 50, 8941-8968.
44. Liebeskind, L. S.; Yu, M. S.; Fengl, R. W. J. Org. Chem. 1993, 58, 3543-3549.
45. Liebeskind, L. S.; Yu, M. S.; Yu, R. H.; Wang, J. Y.; Hagen, K. S. J. Am. Chem. Soc. 1993, 115, 9048-9055.
46. Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359.
47. Liebeskind, L. S.; Wang, J. Tetrahedron Lett. 1990, 31, 4293.
48. Shultz, D. A.; Gwaltney, K. P.; Lee, H. J. Org. Chem. 1998, 63, 4034-4038.
49. Milgrom, L. R.; Yahioglu, G. Tetrahedron Lett. 1996, 37, 4069.
50. Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4992.
51. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
52. Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627-630.
53. Fuhrhop, J.-H. In Irreversible Reaction on the Porphyrin Periphery; Dolphin, D., Ed.; Academic: New York, 1978; Vol. II, p 134.
54. Sanders, J. K. M.; Hunter, B. K. Modern NMR Spectroscopy. A Guide for Chemists, 2nd ed.; Oxford University Press: Oxford, 1993.
55. Sanders, J. K. M.; Hunter, B. K. Modern NMR Spectroscopy. A Guide for Chemists, 2nd ed.; Oxford University Press: Oxford, 1993.
56. Kim, J. B., Adler, A. D.; Longo, F. R. In Synthesis of Porphyrins from Monopyrroles; Dolphin, D., Ed.; Academic Press: New York, 1978; Vol. I, p 89.
57. Gottwald, L. K.; Ullman, E. F. Tetrahedron Lett. 1968, 36, 3071-3074.
58. Collman, J. P.; Gagne, R. R.; Reed, C.; Halbert, T. R.; Lang, G.; Robinson, W. J. Am. Chem. Soc. 1975, 97, 1427-1439.
59. Davis, W. B.; Svec, W. A.; Ratner, M. A.; Wasielewski, M. R. Nature 1998, 396, 60-63.
60. Arnold, D. P.; Johnson, A. W.; Mahendran, M. J. Chem. Soc., Perkin Trans. 1 1978, 366-370.
61. Gouterman, M. In Optical Spectra and Electronic Structure of Porphyrins and Related Rings; Dolphin, D., Ed.; Academic: New York, 1978; Vol. III, pp 1-165.
62. Arnold, D. P.; Bott, R. C.; Eldridge, H.; Elms, F. M.; Smith, G.; Zojaji, M. Aust. J. Chem. 1997, 50, 495.
63. Imahori, H.; Higuchi, H.; Matsuda, Y.; Itagaki, A.; Sakai, Y.; Ojima, J.; Sakata, Y. Bull. Chem. Soc. Jpn. 1994, 67, 2500.
64. Arnold, D. P.; James, D. A. J. Org. Chem. 1997, 62, 3460.
65. Yeung, M.; Ng, A. C. H.; Drew, M. G. B.; Vorpagel, E.; Breitung, E. M.; McMahon, R. J.; Ng, D. K. P. J. Org. Chem. 1998, 63, 7143-7150.
66. Andersen, H. L. Inorg. Chem. 1994, 33, 972.
67. Purchased from Baeckström SEPARO AB, Larsbergsvägen 24, S-181 39 Lindingö, Sweden.
68. Aso, Y.; Yamashita, H.; Otsubo, T.; Ogura, F. J. Org. Chem. 1989, 54, 5627-5629.
69. Schlosser, M. In Organoalkali Reagents; Schlosser, M., Ed.; John Wiley & Sons: Chichester, 1994; pp 1-166.