Syntheses of diaza-18-crown-6 ligands containing two units each of 4- hydroxyazobenzene, benzimidazole, uracil, anthraquinone, or ferrocene groups

Journal of Heterocyclic Chemistry

Volumn 36, Issue 3, 1999, Pages 771-775

  Su, Ning ^a   Bradshaw, Jerald S ^a   Zhang, Xian X ^a   Savage, Paul B ^a   Krakowiak, Krzysztof E ^a,b   Izatt, Reed M ^a  

^a Brigham Young University   (United States)

^b IBC Advanced Technologies Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRAQUINONE; BENZIMIDAZOLE; COPPER COMPLEX; FERROCENE DERIVATIVE; GOLD COMPLEX; PHENOL DERIVATIVE; POTASSIUM DERIVATIVE; SODIUM DERIVATIVE; URACIL;

AMINATION; ARTICLE; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; HYDROGEN BOND; OXIDATION REDUCTION REACTION; REACTION ANALYSIS; SYNTHESIS; THERMODYNAMICS;

EID: 0032812452     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570360332     Document Type: Article

References (44)

1. [a] A. W. Czarnik, Acc. Chem. Res., 27, 302 (1990);
2. [b] L. Fabbrizzi, M. Licchell, P. Pallavicini, A. Perotti, and D. Sacchi, Angew. Chem., Int. Ed. Engl., 33, 1975 (1994);
3. [c] Q. Zhou and T. M. Swager, J. Am. Chem. Soc., 117, 7017 (1995);
4. [d] D. M. Rudkevich, W. Verboom, E. Van Der Tol, C. J. Van Staveren, F. M. Kaspersen, J. W. Verhoeven, and D. N. Reinhoudt, J. Chem. Soc., Perkin Trans. II, 131 (1995);
5. [e] D. Marquis, J.-P. Desvergne, and H. Bouas-Laurent, J. Org. Chem., 60, 7984 (1995);
6. [f] H. Matsumoto and S. Shinkai, Tetrahedron Letters, 37, 77 (1996).
7. [a] A. P. de Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher, and T. E. Rice, Chem. Rev., 97, 1515 (1997);
8. [b] Fluorescent Chemosensors for Ion and Molecular Recognition, A. W. Czarnik, ed., American Chemical Society, Washington, D. C. 1992.
9. Z. Marczenko, Separation and Spectrophotometric Determination of Elements, John Wiley & Sons, New York, 1986.
10. [a] E. Linder, M. Horvath, K. Toth, and E. Pungor, Anal. Letters, 25, 453 (1992);
11. [b] R. A. Bartsch, E. Chapoteau, B. P. Czech, J. Krzykawski, A. Kumar, and T. W. Robinson, J. Org. Chem., 59, 616 (1994);
12. [c] Y. Kobo, S. Maeda, M. Nakamura, and S. Tokita, J. Chem. Soc., 1725 (1994);
13. [d] T. W. Brockmann and J. M. Tour, J. Am. Chem. Soc., 117, 4437 (1995).
14. T. E. Edmonds, Chemical Sensors, Blackie, Glasgow and London, 1988.
15. [a] X. X. Zhang, A. V. Bordunov, J. S. Bradshaw, N. K. Dalley, X. Kou, and R. M. Izatt, J. Am. Chem. Soc., 117, 11507 (1995);
16. [b] A. V. Bordunov, J. S. Bradshaw, X. X. Zhang, N. K. Dalley, X. Kou, and R. M. Izatt, Inorg. Chem., 35, 7229 (1996);
17. [c] J. S. Bradshaw and R. M. Izatt, Acc. Chem. Res., 30, 338 (1997).
18. L. Prodi, F. Bolletta, M. Montali, N. Zaccheroni, P. B. Savage, J. S. Bradshaw, and R. M. Izatt, Tetrahedron Letters, 39, 5451 (1998).
19. A. V. Bordunov, J. S. Bradshaw, V. N. Pastushok, and R. M. Izatt, SynLett, 933 (1996).
20. [a] A. F. Abdel-Magid, K. G. Carson, B. D. Harris, C. A. Maryanoff, and R. D. Shah, J. Org. Chem., 61, 3849 (1996);
21. [b] R. F. Borch and A. I. Hassid, J. Org. Chem., 37, 1673 (1972);
22. [c] F. J. McEvoy and G. R. Allen, J. Med. Chem., 17, 281 (1974).
23. [a] Y. Katayama, R. Fukuda, and M. Takagi, Anal. Chim. Acta., 185, 295 (1986);
24. [b] Y. Katayama, R. Fukuda, K. Hiwatari, and M. Takagi, Rep. Asahi Glass Found. Ind. Technol., 48, 193 (1986).
25. [a] S. Shinkai and O. Manabe, Top. Curr. Chem., 121, 67 (1984);
26. [b] S. Misumi, Pure Appl. Chem., 62, 493 (1990).
27. [a] W. W. Weber, C. R. Messing, and M. E. Logan, European Patent Appl., EP 0 826 677 Al, 1998;
28. [b] S. R. Sandier and W. Karo, Organic Functional Group Preparations Volume II; Academic Press: San Diego, 1986;
29. [c] S. Akabori, Y. Miura, N. Yotsumoto, K. Uchida, M. Kitano, and Y. Habata, J. Chem. Soc., Perkin Trans. I, 2589 (1995).
30. K.-W. Chi, H.-C. Wei, T. Kottke, and R. J. Lagow, J. Org. Chem., 61, 5684 (1996).
31. [a] T. K. Adler, Anal. Chem., 34, 685 (1962);
32. [b] H. V. Schutt and H. Zimmermann, Ber. Bunsenges Phys. Chem., 67, 54 (1963).
33. [a] P. O. P. Ts'o, In Basic Principles in Nucleic Acid Chemistry, P. O. P. Ts'o, ed, Academic Press: New York and London, 1974;
34. [b] P. O. P. Ts'o, In Fine Structure of Proteins and Nucleic Acids, G. D. Fasman and S. N. Timasheff, eds, Marcel Dekker, New York, 1970.
35. A. E. Kaifer and L. A. Echegoyen, In Cation Binding by Macrocyclic Systems, Y. Inoue and G. W. Gokel, eds, Marcel Dekker, New York, 1990.
36. [a] J. C. Medina, T. T. Goodnow, M. Rojas, J. L. Atwood, B. C. Lynn, A. E. Kaifer, and G. W. Gokel, J. Am. Chem. Soc., 114, 10583 (1992);
37. [b] P. D. Beer, J. E. Natiòn, S. L. McWhinnie, M. E. Harman, M. B. Hursthouse, M. I. Ogden, and A. H. White, J. Chem. Soc., Dalton Trans., 2485 (1991).
38. [a] Z. Chen, O. F. Schall, M. Alcala, Y. Li, G. W. Gokel, and L. Echegoyen, J. Am. Chem. Soc., 114, 444 (1992);
39. [b] V. G. Young Jr., H. L. Quiring, and A. G. Sykes, J. Am. Chem. Soc., 119, 12477 (1997).
40. [a] J. L. Oscarson and R. M. Izatt, In Physical Methods of Chemistry Vol VI: Determination of Thermodynamic Properties, B. W. Rossiter and R. C. Baetzold, eds.; John Wiley & Sons: New York, 1992; Chapter 7;
41. [b] R. M. Izatt, X. X. Zhang, H. Y. An, C. Y. Zhu, and J. S. Bradshaw, Inorg. Chem., 33, 1007 (1994).
42. [a] M. Shiga, H. Nishida, H. Nakamura, M. Takagi, and K. Ueno, Bunseki Kagaku, 32, E293 (1993);
43. [b] A. V. Bordunov, P. C. Hellier, J. S. Bradshaw, N. K. Dalley, X.-L. Kou, X. X. Zhang, and R. M. Izatt, J. Org. Chem., 60, 6097 (1995).
44. D. J. Eatough, J. J. Christensen, and R. M. Izatt, Thermochim. Acta, 3, 219 and 233 (1972).