A versatile domino synthesis affording novel S- and U-shaped terpyridines. Synthesis, properties and crystal structure

Liebigs Annales

Volumn , Issue 5, 1996, Pages 705-715

  Keuper, Ralf ^a   Risch, Nikolaus ^a   Flörke, Ulrich ^a   Haupt, Hans Jürgen ^a  

^a UNIVERSITY OF PADERBORN   (Germany)

Author keywords

Dihydropyridines; Domino reaction; Host guest complexes; Terpyridines

Indexed keywords

EID: 33749018223     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199619960511     Document Type: Article

References (53)

1. V. Grosshenny, A. Harriman, R. Ziessel, Angew. Chem. 1995, 107, 1211-1214;
2. Angew. Chem. Int. Ed. Engl. 1995, 34, 1100-1102.
3. A. Juris, R. Ziessel, Inorg. Chim. Acta 1994, 225, 251-254.
4. A. Juris, V. Balzani, P. Belser, F. Barigelletti, S. Campagna, A. v. Zelewsky, Coord. Chem. Rev. 1988, 84, 85-277.
5. F. Vögtle, M. Frank, M. Nieger, P. Belser, A. v. Zelewsky, V. Balzani, F. Barigelletti, L. De Cola, L. Flamigni, Angew. Chem. 1993, 105, 1706-1709;
6. Angew. Chem. Int. Ed. Engl. 1993, 32, 1643-1646.
7. F. Barigelletti, L. Flamingni, V. Balzani, J.-P. Collin, J.-P. Sauvage, A. Sour, E. C. Constable, A. M. W. Cargill Thompson, J. Chem. Soc., Chem. Commun. 1993, 942-944.
8. J.-P. Collin, S. Guillerez, J.-P. Sauvage, F. Barigelletti, L. Flamigni, L. De Cola, V. Balzani, Coord. Chem. Rev. 1991, 111, 291-296.
9. J.-P. Collin, S. Guillerez, J.-P. Sauvage, F. Barigelletti, L. De Cola, L. Flamigni, V. Balzani, Inorg. Chem. 1991, 30, 4230-4238.
10. J.-P. Collin, S. Guillerez, J.-P. Sauvage, F. Barigelletti, L. De Cola, L. Flamigni, V. Balzani, Inorg. Chem. 1992, 31, 4112-4117.
11. L. Boguslavsky, T. W. Bell, Langmuir 1995, 10, 991-993.
12. V. Balzani, L. De Cola, F. Barigelletti, Top. Curr. Chem. 1990, 158, 31-71.
13. J.-P. Sauvage, J.-P. Collin, J.-C. Chambron, S. Guillerez, C. Coudret, V. Balzani, F. Barigelletti, L. De Cola, L. Flamigni, Chem. Rev. 1994, 94, 993-1019.
14. V. Balzani, S. Campagna, G. Denti, A. Juris, S. Serroni, M. Venturi, Coord. Chem. Rev. 1994, 132, 1-13.
15. G. Denti, S. Campagna, S. Serroni, M. Ciano, V. Balzani, J. Am. Chem. Soc. 1992, 114, 2944-2950.
16. G. Denti, S. Campagna, L. Sabatino, S. Serroni, M. Ciano, V. Balzani, Inorg. Chem. 1990, 29, 4750-4758.
17. S. Campagna, G. Denti, S. Serroni, A. Juris, M. Venturi, V. Ricevuto, V. Balzani, Chem. Eur. J. 1995, 1, 211-221.
18. V. Grosshenny, R. Ziessel, Tetrahedron Lett. 1992, 33, 8075-8078.
19. V. Grosshenny, R. Ziessel, J. Organomet. Chem. 1993, 453, C19-C22.
20. V. Grosshenny, R. Ziessel, J. Chem. Soc., Dalton Trans. 1993, 817-819.
21. J.-M. Lehn, Supramolecular Chemistry -Concepts and Perspectives, VCH, 1995.
22. A. E. Friedman, J.-C. Chambron, J.-P. Sauvage, N. J. Turro, J. K. Barton, J. Am. Chem. Soc. 1990, 112, 4960-4962.
23. N. Risch, R. Keuper, Z. Naturforsch. 1995, 50b, 1115-1120.
24. U. Westerwelle, N. Risch, Tetrahedron Lett. 1993, 34, 1775-1778.
25. R. Troschütz, H. J. Roth, Arch. Pharm. 1978, 311, 406-411.
26. R. Troschütz, H. J. Roth, Arch. Pharm. 1978, 311, 542-547.
27. R. M. Kellogg, T. J. van Bergen, H. van Doren, D. Hedstrand, J. Kooi, W. H. Kruizinga, C. B. Troostwijk, J. Org. Chem. 1980, 45, 2854-2861.
28. F. Bossert, H. Meyer, E. Wehinger, Angew. Chem. 1981, 93, 755-763;
29. Angew. Chem. Int. Ed.Engl 1981, 20, 762-769.
30. R. Mannhold, Pharm. in unserer Zeit 1995, 24, 137-153.
31. C.-Y. Huang, V. Lynch, E. V. Anslyn, Angew. Chem. 1992, 104, 1259-1261;
32. Angew. Chem. Int. Ed. Engl. 1992, 31, 1244-1246.
33. R. P. Thummel: private communication.
34. Further details of the crystal structure determination are available on request from the Fachinformationszentrum Karlsruhe, Gesellschaft für wissenschaftlich-technische Information mbH, D-76344 Eggenstein-Leopoldshafen, on quoting the depository numbers CSD-404141 for 8c, CSD-404140 for 8e, CSD-404279 for 6h, the names of the authors, and the journal citation.
35. G. M. Sheldrick, SHELXTL-Plus, Structure Determination Software Programs, Siemens Analytical X-ray Instr. Inc., Madison, Wisconsin, USA, 1990.
36. G. M. Sheldrick, SHELXL-93, Program for Crystal Structure Refinement, Universität Göttingen, Germany, 1993.
37. N. I. Leonhard, J. V. Paukstelis, J. Org. Chem. 1963, 28, 3021-3024.
38. G. Kinast, L. F. Tietze, Angew. Chem. 1976, 88, 261-262;
39. Angew. Chem. Int. Ed Engl. 1976, 15, 239.
40. H. Böhme, G. Auterhoff, Chem. Ber. 1971, 104, 2013-2017.
41. U. Westerwelle, Dissertation, Universität Bielefeld, 1994.
42. R. A. Henry, W. M. Dehn, J. Am. Chem. Soc. 1949, 71, 2271-2273.
43. R. P. Thummel, F. Lefoulon, D. Cantu, R. Mahadevan, J. Org. Chem. 1984, 49, 2208-2212.
44. V. Hedge, Y. Jahng, R. P. Thummel, Tetrahedron Lett. 1987, 28, 4023-4026.
45. R. P. Thummel, Y. Jahng, J. Org. Chem. 1985, 50, 2407-2412.
46. T. W. Bell, Y.-M. Cho, A. Firestone, K. Healy, J. Liu, R. Ludwig, S. D. Rothenberger, Org. Synth. Coll. Vol. VIII 1993, 87-93;
47. T. W. Bell, P. J. Cragg, M. G. B. Drew, A. Firestone, A. D.-I. Kwok, J. Liu, R. T. Ludwig, A. T. Papoulis, Pure and Applied Chem. 1993, 65, 361-366;
48. T. W. Bell, Crown Compounds: Towards Future Applications 1992, 305-318;
49. T. W. Bell, A. Firestone, J. Am. Chem. Soc. 1986, 108, 7427-7428;
50. T. W. Bell, A. Firestone, J. Liu, R. Ludwig, S. D. Rothenberger, Inclusion Phenomena and Molecular Recognition 1990, 49-56.
51. E. Klingsberg, The Chemistry of Heterocyclic compounds, Pyridine and Its Derivatives, Interscience Publishers, 1962, Part I, 80, 500;
52. E. Klingsberg, The Chemistry of Heterocyclic compounds, Pyridine and Its Derivatives, ibid. Part III, 181;
53. E. Klingsberg, The Chemistry of Heterocyclic compounds, Pyridine and Its Derivatives, ibid. Part IV, 142.