Synthesis of fluorinated fluoresceins

Journal of Organic Chemistry

Volumn 62, Issue 19, 1997, Pages 6469-6475

  Sun, Wei Chuan ^a   Gee, Kyle R ^a   Klaubert, Dieter H ^a   Haugland, Richard P ^a  

^a MOLECULAR PROBES INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORESCEIN DERIVATIVE; NITROBENZENE DERIVATIVE; PHTHALIC ACID; RESORCINOL DERIVATIVE;

ARTICLE; BLEACHING; CHEMICAL STRUCTURE; DEMETHYLATION; DERIVATIZATION; FLUORIDATION; IONIZATION; QUANTUM CHEMISTRY; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030764693     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9706178     Document Type: Article

References (43)

1. von Bayer, A. Chem. Ber. 1871, 5, 255.
2. Guilbault, G. G. In Practical Fluorescence; Guilbault, G. G., Ed.; Marcel Dekker Inc.: New York, 1990; Chapter 1.
3. For convenience, only 5-isomers are shown; the numbering system is depicted in Scheme 1.
4. For a source book and comprehensive references, see: Haugland, R. P. Handbook of Fluorescent Probes and Research Chemicals, 6th ed.; Molecular Probes Inc.: Eugene, OR, 1996.
5. (a) Song, L.; Hennink, E. J.; Young, T.; Tanke, H. J. Biophys. J. 1995, 68, 2588.
6. (b) Song, L.; Varma, C. A. G. O.; Verhoeven, J. W.; Tanke, H. Biophys. J. 1996, 70, 2959.
7. Sjoback, R.; Nygern, J.; Kubista, M. Spectrochim. Acta Part A 1995, 51, L7.
8. Guilbault, G. G. In Practical Fluorescence; Guilbault, G. G., Ed.; Marcel Dekker Inc.: New York, 1990; Chapter 6.
9. Ibid.; pp 129-141.
10. (a) Chapple, M. R.; Johnson, G. D.; Davidson, R. S. J. Microsc. 1990, 159, 254.
11. (b) Chen, R. F.; Knutson, J. R. Anal. Biochem. 1988, 172, 61.
12. Lentz, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 1315 and references cited therein.
13. (a) Schultz. Farbstofftabellen; Akademisch Verlagsgesellschaft m.b.H.: Leipzig, 1885.
14. (b) Review: Neckers, D. C. J. Photochem. Photobiol. A: Chem. 1989, 47, 1.
15. Linden, S. M.; Neckers, D. C. J. Am. Chem. Soc. 1988, 110, 1257.
16. For fluorination with N-fluoropyridinium salts, see: (a) Umemoto, T.; Fukami, S.; Tomizawa, G.; Harasawa, K.; Kawada, K.; Tomita, K. J. Am. Chem. Soc. 1990, 112, 8563. (b) Umemoto, T.; Tomizawa, G. J. Org. Chem. 1995, 60, 6563. With N-fluoro-N-(phenylsulfonyl)benzenesulfonamide and related compounds, see: (c) Differding, E.; Ofner, H. Synlett 1991, 187. (d) Singh, S.; DesMarteau, D. D.; Zuberi, S. S.; Witx, M.; Huang, H.-N. Synlett 1987, 109, 7194. (e) Barnette, W. E. J. Am. Chem. Soc. 1984, 106, 452. With Selectfluor, see: (f) Banks, R. E. U.S. Patent 5086178, 1992. (g) Banks, R. E.; Mohialdin-Khaffaf, S. N.; Lal, G. S.; Sharif, I.; Syvret, G. J. Chem. Soc., Chem. Commun. 1992, 596. (h) Lal, G. S. J. Org. Chem. 1993, 58, 2791.
17. For fluorination with N-fluoropyridinium salts, see: (a) Umemoto, T.; Fukami, S.; Tomizawa, G.; Harasawa, K.; Kawada, K.; Tomita, K. J. Am. Chem. Soc. 1990, 112, 8563. (b) Umemoto, T.; Tomizawa, G. J. Org. Chem. 1995, 60, 6563. With N-fluoro-N-(phenylsulfonyl)benzenesulfonamide and related compounds, see: (c) Differding, E.; Ofner, H. Synlett 1991, 187. (d) Singh, S.; DesMarteau, D. D.; Zuberi, S. S.; Witx, M.; Huang, H.-N. Synlett 1987, 109, 7194. (e) Barnette, W. E. J. Am. Chem. Soc. 1984, 106, 452. With Selectfluor, see: (f) Banks, R. E. U.S. Patent 5086178, 1992. (g) Banks, R. E.; Mohialdin-Khaffaf, S. N.; Lal, G. S.; Sharif, I.; Syvret, G. J. Chem. Soc., Chem. Commun. 1992, 596. (h) Lal, G. S. J. Org. Chem. 1993, 58, 2791.
18. For fluorination with N-fluoropyridinium salts, see: (a) Umemoto, T.; Fukami, S.; Tomizawa, G.; Harasawa, K.; Kawada, K.; Tomita, K. J. Am. Chem. Soc. 1990, 112, 8563. (b) Umemoto, T.; Tomizawa, G. J. Org. Chem. 1995, 60, 6563. With N-fluoro-N-(phenylsulfonyl)benzenesulfonamide and related compounds, see: (c) Differding, E.; Ofner, H. Synlett 1991, 187. (d) Singh, S.; DesMarteau, D. D.; Zuberi, S. S.; Witx, M.; Huang, H.-N. Synlett 1987, 109, 7194. (e) Barnette, W. E. J. Am. Chem. Soc. 1984, 106, 452. With Selectfluor, see: (f) Banks, R. E. U.S. Patent 5086178, 1992. (g) Banks, R. E.; Mohialdin-Khaffaf, S. N.; Lal, G. S.; Sharif, I.; Syvret, G. J. Chem. Soc., Chem. Commun. 1992, 596. (h) Lal, G. S. J. Org. Chem. 1993, 58, 2791.
19. For fluorination with N-fluoropyridinium salts, see: (a) Umemoto, T.; Fukami, S.; Tomizawa, G.; Harasawa, K.; Kawada, K.; Tomita, K. J. Am. Chem. Soc. 1990, 112, 8563. (b) Umemoto, T.; Tomizawa, G. J. Org. Chem. 1995, 60, 6563. With N-fluoro-N-(phenylsulfonyl)benzenesulfonamide and related compounds, see: (c) Differding, E.; Ofner, H. Synlett 1991, 187. (d) Singh, S.; DesMarteau, D. D.; Zuberi, S. S.; Witx, M.; Huang, H.-N. Synlett 1987, 109, 7194. (e) Barnette, W. E. J. Am. Chem. Soc. 1984, 106, 452. With Selectfluor, see: (f) Banks, R. E. U.S. Patent 5086178, 1992. (g) Banks, R. E.; Mohialdin-Khaffaf, S. N.; Lal, G. S.; Sharif, I.; Syvret, G. J. Chem. Soc., Chem. Commun. 1992, 596. (h) Lal, G. S. J. Org. Chem. 1993, 58, 2791.
20. For fluorination with N-fluoropyridinium salts, see: (a) Umemoto, T.; Fukami, S.; Tomizawa, G.; Harasawa, K.; Kawada, K.; Tomita, K. J. Am. Chem. Soc. 1990, 112, 8563. (b) Umemoto, T.; Tomizawa, G. J. Org. Chem. 1995, 60, 6563. With N-fluoro-N-(phenylsulfonyl)benzenesulfonamide and related compounds, see: (c) Differding, E.; Ofner, H. Synlett 1991, 187. (d) Singh, S.; DesMarteau, D. D.; Zuberi, S. S.; Witx, M.; Huang, H.-N. Synlett 1987, 109, 7194. (e) Barnette, W. E. J. Am. Chem. Soc. 1984, 106, 452. With Selectfluor, see: (f) Banks, R. E. U.S. Patent 5086178, 1992. (g) Banks, R. E.; Mohialdin-Khaffaf, S. N.; Lal, G. S.; Sharif, I.; Syvret, G. J. Chem. Soc., Chem. Commun. 1992, 596. (h) Lal, G. S. J. Org. Chem. 1993, 58, 2791.
21. For fluorination with N-fluoropyridinium salts, see: (a) Umemoto, T.; Fukami, S.; Tomizawa, G.; Harasawa, K.; Kawada, K.; Tomita, K. J. Am. Chem. Soc. 1990, 112, 8563. (b) Umemoto, T.; Tomizawa, G. J. Org. Chem. 1995, 60, 6563. With N-fluoro-N-(phenylsulfonyl)benzenesulfonamide and related compounds, see: (c) Differding, E.; Ofner, H. Synlett 1991, 187. (d) Singh, S.; DesMarteau, D. D.; Zuberi, S. S.; Witx, M.; Huang, H.-N. Synlett 1987, 109, 7194. (e) Barnette, W. E. J. Am. Chem. Soc. 1984, 106, 452. With Selectfluor, see: (f) Banks, R. E. U.S. Patent 5086178, 1992. (g) Banks, R. E.; Mohialdin-Khaffaf, S. N.; Lal, G. S.; Sharif, I.; Syvret, G. J. Chem. Soc., Chem. Commun. 1992, 596. (h) Lal, G. S. J. Org. Chem. 1993, 58, 2791.
22. For fluorination with N-fluoropyridinium salts, see: (a) Umemoto, T.; Fukami, S.; Tomizawa, G.; Harasawa, K.; Kawada, K.; Tomita, K. J. Am. Chem. Soc. 1990, 112, 8563. (b) Umemoto, T.; Tomizawa, G. J. Org. Chem. 1995, 60, 6563. With N-fluoro-N-(phenylsulfonyl)benzenesulfonamide and related compounds, see: (c) Differding, E.; Ofner, H. Synlett 1991, 187. (d) Singh, S.; DesMarteau, D. D.; Zuberi, S. S.; Witx, M.; Huang, H.-N. Synlett 1987, 109, 7194. (e) Barnette, W. E. J. Am. Chem. Soc. 1984, 106, 452. With Selectfluor, see: (f) Banks, R. E. U.S. Patent 5086178, 1992. (g) Banks, R. E.; Mohialdin-Khaffaf, S. N.; Lal, G. S.; Sharif, I.; Syvret, G. J. Chem. Soc., Chem. Commun. 1992, 596. (h) Lal, G. S. J. Org. Chem. 1993, 58, 2791.
23. For fluorination with N-fluoropyridinium salts, see: (a) Umemoto, T.; Fukami, S.; Tomizawa, G.; Harasawa, K.; Kawada, K.; Tomita, K. J. Am. Chem. Soc. 1990, 112, 8563. (b) Umemoto, T.; Tomizawa, G. J. Org. Chem. 1995, 60, 6563. With N-fluoro-N-(phenylsulfonyl)benzenesulfonamide and related compounds, see: (c) Differding, E.; Ofner, H. Synlett 1991, 187. (d) Singh, S.; DesMarteau, D. D.; Zuberi, S. S.; Witx, M.; Huang, H.-N. Synlett 1987, 109, 7194. (e) Barnette, W. E. J. Am. Chem. Soc. 1984, 106, 452. With Selectfluor, see: (f) Banks, R. E. U.S. Patent 5086178, 1992. (g) Banks, R. E.; Mohialdin-Khaffaf, S. N.; Lal, G. S.; Sharif, I.; Syvret, G. J. Chem. Soc., Chem. Commun. 1992, 596. (h) Lal, G. S. J. Org. Chem. 1993, 58, 2791.
24. Durrani, A. A.; Tyman, J. H. P. J. Chem. Soc., Perkin Trans. 1 1980, 1658.
25. Suschitzky, H. Adv. Fluorine Chem. 1965, 1, 10. An improved method for fluorodediazoniation of arylamines substituted with a polar group (including an o-methoxy group) was recently reported; see: Sasaki, K.; Oishi, M.; Imaki, N. J. Fluorine Chem. 1996, 76, 59.
26. Suschitzky, H. Adv. Fluorine Chem. 1965, 1, 10. An improved method for fluorodediazoniation of arylamines substituted with a polar group (including an o-methoxy group) was recently reported; see: Sasaki, K.; Oishi, M.; Imaki, N. J. Fluorine Chem. 1996, 76, 59.
27. Patrick, T. B.; Darling, D. L. J. Org. Chem. 1986, 51, 3242.
28. During the preparation of this manuscript J. J. Yang, R. L. Kirchmeier, and J. M. Shreeve reported similar results which appeared at: Thirteenth Winter Fluorine Conference, St. Petersburg Beach, FL, Jan. 19-24, 1997; Poster P32.
29. Confalone, P. N. J. Heterocycl. Chem. 1990, 27, 31.
30. Obtained in one step from commercially available 3,5-dimethoxy-fluorobenzene.
31. For example: Abs/Em for 2′,7′-dichlorocarboxyfluorescein = 540/529 nm; 2′,4′,5′,7′-tetrabromofluorescein = 520/543 nm; 2′,4′,5′,7′-tetraiodofluorescein = 528/553 nm.
32. a of the 6′-phenol.
33. (a) Fujio, M.; McIver, R. T., Jr.; Taft, R. W. J. Am. Chem. Soc. 1981 103 4017.
34. (b) Dolbier, W. R., Jr.; Burkholder, C.; Abboud, K. A.; Loehle, D. J. Org. Chem. 1994, 59, 7688.
35. Reference 5a and references cited therein.
36. The band pass was 20 nm and centered at the excitation maximum.
37. (a) Yagupol'skii, L. M.; Il'chenko, A. Ya.; Gandel sman, L. Z. Russ. Chem. Rev. 1993, 52, 993.
38. (b) Herd, K. J. Fluorine-containing dyes In Organofluorine Chemistry: Principles and Commercial Applications; Banks, R. E., et al. Eds.; Plenum Press: New York; Chapter 13.
39. Tsien, R. Y.; Waggoner, A. Fluorophores for confocal microscopy: photophysics and photochemistry. In The Handbook for Biological Confocal Microscopy; Pawley, J., Ed.; IMR Press: Madison, WI, 1994; pp 153-161.
40. Lindqvist, L. Arkiv Kemi. 1960, 16, 79.
41. Gollnick, K.; Franken, T.; Fouda, M. F. R.; Paur, H. R.; Held. S. J. Photochem. Photobiol. B: Biol. 1992, 12, 57.
42. Gee, K. R.; Sun, W.-C.; Klaubert, D. H.; Haugland, R. P.; Upson, R.; Steinberg, T.; Foot, M. Tetrahedron Lett. 1996, 37, 7905.
43. Sun, W.-C.; You, W.; Gee, K. R.; Mao, F.; Klaubert, D. H.; Kramer, J.; Haugland, R. P.; Haugland, R. P. Presented at Experimental Biology '96, Washington, DC, April 14-17, 1996; Paper 11496.