Azolidene Carbenes Derived from Biologically Relevant Molecules. Synthesis and Characterization of Iridium Complexes of Imidazolidene Ligands Based upon the Antifungal Drugs Econazole and Miconazole

Inorganic Chemistry

Volumn 37, Issue 21, 1998, Pages 5412-5413

  Davis Jr , James H ^a   Lake, Charles M ^b   Bernard, Melissa A ^a  

^a UNIVERSITY OF SOUTH ALABAMA   (United States)

^b UNIVERSITY OF ALABAMA AT BIRMINGHAM   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005361849     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic9806277     Document Type: Article

References (31)

1. Presented in part at the 214th National Meeting of the American Chemical Society, Las Vegas, NV, September 1997; Abstract INOR 378.
2. Roth, H. J.; Kleeman, A. Pharmaceutical Chemistry; John Wiley: New York, 1988; p 218.
3. Joule, J. A.; Mills, K.; Smith, G. F. Heterocyclic Chemistry, 3rd ed.; Chapman & Hall: New York, 1995.
4. (a) Reference 3.
5. (b) Arduengo, A. J., III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361.
6. (c) Arduengo, A. J., III: Dias, H. V. R.; Harlow, R. L.; Klooster, W. T.; Koetzle, T. F. J. Am. Chem. Soc. 1994, 116, 6812.
7. (d) Alder, R. W.; Allen, P. R.; Williams, S. J. J. Chem. Soc., Chem. Commun. 1995, 1267.
8. (a) Breslow, R. J. Am. Chem. Soc. 1957, 79, 1762.
9. (b) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719.
10. (a) Wanzlick, H.-W.; Schönherr, H.-J. Angew. Chem., Int. Ed. Engl. 1968, 7, 141.
11. (b) Öfele, K. J. Organomet. Chem. 1968, 12, P42.
12. (c) Herrmann, W. A.; Kocher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2163.
13. (a) Transmethylation: Proceedings of the Conference on Transmethylation, Bethesda, Maryland, U.S.A., on October 16-19, 1978; Usdin, E., Borchardt, T., Creveling, C. R., Eds.; Developments in Neuroscience; Elsevier/North Holland: New York, 1979; Vol. 5.
14. (b) DNA Methylation: Biochemistry and Biological Significance; Razin, A., Cedar, H., Riggs, A. D., Eds.; Springer Series in Molecular Biology; Springer Verlag: New York, 1984.
15. Bray, M. R.; Deeth, R. J. J. Chem. Soc., Dalton Trans. 1997, 4005.
16. (a) Sanchez-Delgado, R. A.; Lazardi, K.; Rincon, L.; Urbina, J. A. J. Med. Chem. 1993, 36, 2041.
17. (b) Sanchez-Delgado, R. A.; Perez, H.; Urbina, J. A. J. Med. Chem. 1996, 39, 1095.
18. (c) Sanchez-Delgado, R. A.; Perez, H.; Navarro, M. J. Med. Chem. 1997, 40, 1937.
19. Sigma Chemical Company, St. Louis, MO.
20. Caution! Methyl iodide is highly towic. Handle with care in an efficient fume hood.
21. Pietzonka, T.; Seebach, D. Chem. Ber. 1991, 124, 1837.
22. 2O); 4.85 (m, 1H, COD); 5.41 (m, 1H, COD); 6.76 (d, 1H, imidazole H); 6.99 (d, 1H, imidazole H); 7.10-7.18 (m, 2H, aryl); 7.23-7.34 (m, 3H, aryl); 7.44 (m, 1H, aryl); 7.54 (m, 1H, aryl). All reported data for major (chloro) derivative.
23. Kocher, C.; Herrmann, W. A. J. Organomet. Chem. 1997, 532, 261 and references therein.
24. 18
25. Siemens SHELXTL-PC Manual, release 4.1; Siemens Analytical Instruments: Madison, WI, 1990.
26. International Tables for Crystallography; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1995; Vol. C. pp 713-791.
27. 20 The disordered chlorine and iodine atoms are in too close a proximity to be effectively resolved by the X-ray study. The resulting Ir-X bond distance is a statistical average of these two different Ir-halogen distances, During refinement, a hybrid iodo/chloro atom was inserted into the halogen site with occupancy k = 0.264 for I and 0.736 for Cl.
28. Churchill, M. R. Inorg. Chem. 1973, 12, 1213.
29. -).
30. 2O); 4.86 (dd, 1H, COD); 5.44 (dd, 1H, COD); 6.75 (d, 1H, imidazole H); 6.99 (d, 1H, imidazole H); 7.13-7.28 (m, 4H, aryl); 7.44 (m, 1H, aryl); 7.52 (d, 1H, aryl).
31. 4IIrO: C, 37.82; H, 3.29; N, 3.27. Found: C, 37.75; H, 3.23; N, 3.10.