Synthesis of 4,7-Disubstituted Phenanthrolines as Key Building Blocks for the First Preparation of Macrocyclic Mono- and Bisphenanthrolines with exo-Coordination Sites

Synlett

Volumn 1997, Issue 6, 1997, Pages 710-712

  Schmittel, Michael ^a   Ganz, Andrea ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003089146     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-3243     Document Type: Article

References (24)

1. Dietrich-Buchecker, C. O.; Frommberger, B.; Lüer, I.; Sauvage, J.-P.; Vögtle, F.; Angew. Chem., Int. Ed. Engl. 1993, 32, 1434; Amabilino, D. B.; Ashton, P. R.; Reder, A. S.; Spencer, N.; Stoddart, J. F.; Angew. Chem., Int. Ed. Engl. 1994, 33, 433
2. Dietrich-Buchecker, C. O.; Frommberger, B.; Lüer, I.; Sauvage, J.-P.; Vögtle, F.; Angew. Chem., Int. Ed. Engl. 1993, 32, 1434; Amabilino, D. B.; Ashton, P. R.; Reder, A. S.; Spencer, N.; Stoddart, J. F.; Angew. Chem., Int. Ed. Engl. 1994, 33, 433
3. Solladié, N.; Chambron, J.-C.; Dietrich-Buchecker, C. O.; Sauvage, J.-P.; Angew. Chem., Int. Ed. Engl. 1996, 35, 906.
4. Dietrich-Buchecker, C. O.; Guilhem, J.; Pascard, C.; Sauvage, J.-P.; Angew. Chem., Int. Ed. Engl. 1990, 29, 1145; Zhu, S. S.; Caroll, P. J.; Swager, T. M.; J. Am. Chem. Soc. 1996, 118, 8713.
5. Dietrich-Buchecker, C. O.; Guilhem, J.; Pascard, C.; Sauvage, J.-P.; Angew. Chem., Int. Ed. Engl. 1990, 29, 1145; Zhu, S. S.; Caroll, P. J.; Swager, T. M.; J. Am. Chem. Soc. 1996, 118, 8713.
6. Chambron, J.-C.; Sauvage, J.-P.; Tetrahedron Lett. 1986, 27, 865; Chambron, J.-C.; Sauvage, J.-P.; Tetrahedron 1987, 43, 895; Dürr, H.; Kilburg, H.; Bossmann, S.; Synthesis 1990, 773; Kaes, C.; Hosseini, M. W.; Ruppert, R.; De Cian, A.; Fischer, J.; Tetrahedron Lett. 1994, 35, 7233; Kaes, C.; Hosseini, M. W.; Ruppert, R.; De Cian, A.; Fischer, J.; J. Chem. Soc., Chem. Commun. 1995, 1445.
7. Chambron, J.-C.; Sauvage, J.-P.; Tetrahedron Lett. 1986, 27, 865; Chambron, J.-C.; Sauvage, J.-P.; Tetrahedron 1987, 43, 895; Dürr, H.; Kilburg, H.; Bossmann, S.; Synthesis 1990, 773; Kaes, C.; Hosseini, M. W.; Ruppert, R.; De Cian, A.; Fischer, J.; Tetrahedron Lett. 1994, 35, 7233; Kaes, C.; Hosseini, M. W.; Ruppert, R.; De Cian, A.; Fischer, J.; J. Chem. Soc., Chem. Commun. 1995, 1445.
8. Chambron, J.-C.; Sauvage, J.-P.; Tetrahedron Lett. 1986, 27, 865; Chambron, J.-C.; Sauvage, J.-P.; Tetrahedron 1987, 43, 895; Dürr, H.; Kilburg, H.; Bossmann, S.; Synthesis 1990, 773; Kaes, C.; Hosseini, M. W.; Ruppert, R.; De Cian, A.; Fischer, J.; Tetrahedron Lett. 1994, 35, 7233; Kaes, C.; Hosseini, M. W.; Ruppert, R.; De Cian, A.; Fischer, J.; J. Chem. Soc., Chem. Commun. 1995, 1445.
9. Chambron, J.-C.; Sauvage, J.-P.; Tetrahedron Lett. 1986, 27, 865; Chambron, J.-C.; Sauvage, J.-P.; Tetrahedron 1987, 43, 895; Dürr, H.; Kilburg, H.; Bossmann, S.; Synthesis 1990, 773; Kaes, C.; Hosseini, M. W.; Ruppert, R.; De Cian, A.; Fischer, J.; Tetrahedron Lett. 1994, 35, 7233; Kaes, C.; Hosseini, M. W.; Ruppert, R.; De Cian, A.; Fischer, J.; J. Chem. Soc., Chem. Commun. 1995, 1445.
10. Chambron, J.-C.; Sauvage, J.-P.; Tetrahedron Lett. 1986, 27, 865; Chambron, J.-C.; Sauvage, J.-P.; Tetrahedron 1987, 43, 895; Dürr, H.; Kilburg, H.; Bossmann, S.; Synthesis 1990, 773; Kaes, C.; Hosseini, M. W.; Ruppert, R.; De Cian, A.; Fischer, J.; Tetrahedron Lett. 1994, 35, 7233; Kaes, C.; Hosseini, M. W.; Ruppert, R.; De Cian, A.; Fischer, J.; J. Chem. Soc., Chem. Commun. 1995, 1445.
11. a) Levis, M.; Lüning, U.; Müller, M.; Schmittel, M.; Wöhrle, C.; Z. Naturforsch. 1994, 49b, 675;
12. b) Schmittel, M.; Ammon, H.; Wöhrle, C.; Chem. Ber. 1995, 128, 845;
13. c) Schmittel, M.; Ammon, H.; J. Chem. Soc., Chem. Commun. 1995, 687.
14. Schilt, A. A.; Analytical Applications of 1,10-phenanthroline and Related Compounds, Pergamon Press, Oxford 1969; Molock, F. F.; Boykin, D. W.; J. Heterocyclic Chem. 1983, 20, 681; Katritzky, A. R.; Long, Q.-H.; Malhotra, N.; Ramanarayanan, T. A.; Vedage, H.; Synthesis 1992, 911.
15. Schilt, A. A.; Analytical Applications of 1,10-phenanthroline and Related Compounds, Pergamon Press, Oxford 1969; Molock, F. F.; Boykin, D. W.; J. Heterocyclic Chem. 1983, 20, 681; Katritzky, A. R.; Long, Q.-H.; Malhotra, N.; Ramanarayanan, T. A.; Vedage, H.; Synthesis 1992, 911.
16. Schilt, A. A.; Analytical Applications of 1,10-phenanthroline and Related Compounds, Pergamon Press, Oxford 1969; Molock, F. F.; Boykin, D. W.; J. Heterocyclic Chem. 1983, 20, 681; Katritzky, A. R.; Long, Q.-H.; Malhotra, N.; Ramanarayanan, T. A.; Vedage, H.; Synthesis 1992, 911.
17. 3): δ = 7.43-7.46 (m. 6 H, 3′-H, 4′-H, 5′-H), 7.68-7.72 (m, 4 H, 2′-H, 6′-H), 7.80 (d, J = 4.6 Hz, 2 H, 3-H, 8-H), 8.46 (s, 2 H, 5-H, 6-H), 9.16 (d, J = 4.6 Hz, 2 H, 2-H, 9-H).
18. 2: 428.1313, found: 428.1322.
19. Case, F. H.; J. Org. Chem. 1951, 16, 941.
20. Freier, H. F.; Snyder, H. R.; J. Am. Chem. Soc. 1946, 68, 1320.
21. 2O: C 69.56 H, 4.38 N, 6.76: found C 69.25, H 4.70, N 6.30.
22. Schmittel, M.; Ganz, A.; unpublished results.
23. +): calcd. 1109.42, found 1109.25.
24. Schmittel, M.; Ganz, A.; Chem. Commun. 1997, in press.