Synthesis and structural studies of 5,12-dioxocyclams capped by 4-substituted pyridines across the amine nitrogens

Journal of Organic Chemistry

Volumn 68, Issue 20, 2003, Pages 7661-7666

  Achmatowicz, Michal ^a   Hegedus, Louis S ^a   David, Scott ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON-DONATING GROUPS;

CATALYSIS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

5,12 DIOXOCYCLAM DERIVATIVE; AMINE; COPPER COMPLEX; CYANIDE; MACROCYCLIC COMPOUND; NITRIC OXIDE; NITROGEN DERIVATIVE; NITROGEN DIOXIDE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; COMPLEX FORMATION; ELECTRON TRANSPORT; STRUCTURE ANALYSIS; SYNTHESIS;

AMINES; COPPER; CRYSTALLOGRAPHY, X-RAY; HETEROCYCLIC COMPOUNDS; NITROGEN; PYRIDINES;

EID: 0141818066     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0301393     Document Type: Article

References (39)

1. For reviews on dioxocyclams, see: (a) Kimura, E. Pure Appl. Chem. 1989, 61, 823-828.
2. (b) Kimura, E. New developments in macrocyclic polyamine chemistry. In Crown Ethers and Analogous Compounds; Hiraoka, M., Ed.; Elsevier: New York, 1992; Studies in Organic Chemistry, Vol. 45, pp 381-478.
3. (c) Krakowiak, K. E.; Bradshaw, J. S. Ind. Eng. Chem. Res. 2000, 39, 3499-3507.
4. (a) Puntener, K.; Hellman, M. D.; Kuester, E.; Hegedus, L. S. J. Org. Chem. 2000, 65, 8301-8306.
5. (b) Kuester, E.; Hegedus, L. S. Organometallics 1999, 18, 5318-5321.
6. (c) Hsiao, Y.; Hegedus, L. S. J. Org. Chem. 1997, 62, 3586-3591.
7. (d) Dumas, S.; Lastra, E.; Hegedus, L. S. J. Am. Chem. Soc. 1995, 117, 3368-3379.
8. (e) Hegedus, L. S.; Moser, W. H. J. Org. Chem. 1994, 59, 7779-7784.
9. (f) Betschart, C.; Hegedus, L. S. J. Am. Chem. Soc. 1992, 114, 5010-5017.
10. (a) Kurosaki, H.; Yoshida, H.; Fujimoto, A.; Goto, M.; Shionoya, M.; Kimura, E.; Espinosa, E.; Barbe, J.-M.; Guilard, R. J. Chem. Soc., Dalton Trans. 2001, 898-901.
11. (b) Kurosaki, H.; Bucher, C.; Espinosa, E.; Barbe, J.-M.; Guilard, R. Inorg. Chim. Acta 2001, 322, 145-149.
12. (c) Denat, F.; Brandes, S.; Guilard, R. Synlett 2000, 561-574.
13. (d) Brandès, S.; Denat, F.; Lacour, S. Rabiet, F.; Barbette, F.; Pullumbi, P.; Guilard, R. Eur. J. Org. Chem. 1998, 2349, 9-2360.
14. (e) Denat, F.; Lacour, S.; Brandès, S.; Guilard, R. Tetrahedron Lett. 1997, 38, 4417-4420.
15. Wynn, T.; Hegedus, L. S. J. Am. Chem. Soc. 2000, 122, 5034-5042.
16. Hegedus, L. S.; Sundermann, M. J.; Dorhout, P. K. Inorg. Chem. 2003, 42, 4346-4354.
17. For recent reviews, see: (a) Navarro, J. A. R.; Lippert, B. Coord. Chem. Rev. 2001, 222, 219-250.
18. (b) Swiegers, G. F.; Malefetse, T. J. Chem. Rev. 2000, 100, 3483-3538.
19. (c) Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853-908.
20. (d) Fujita, M.; Chem. Soc. Rev. 1998, 27, 417-425.
21. (a) Baxter, P. N. W. J. Org. Chem. 2000, 65, 1257-1272.
22. (b) Ziessel, R.; Hissler, M.; El-ghayoury, A.; Harriman, A. Coord. Chem. Rev. 1998, 178-180, 1251-1298.
23. (c) Hanack, M.; Kamenzin, S.; Kamenzin, C.; Subramanian, L. R. Synth. Met. 2000, 110, 93-103.
24. (d) Geiss, A.; Vahrenkamp, H. Inorg. Chem. 2000, 39, 4029-4036.
25. Teixidor, F.; Anglès, P.; Viñas, C.; Kivekäs, R.; Sillanpää, R. Inorg. Chem. 2001, 40, 4010-4015.
26. Boekelheide, V.; Linn, W. J. J. Am. Chem. Soc. 1954, 76, 1286-1291.
27. Liu, P.; Chen, Y.; Deng, J.; Tu, Y. Synthesis 2001, 2078-2080.
28. Feely, W. E.; Beavers, E. M. J. Am. Chem. Soc. 1959, 81, 4004-4007.
29. Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry; Pergamon: Amsterdam, 2000.
30. Tahri, A.; Cielen, E.; Van Aken, K. J.; Hoornaert, G. J.; De Schryver, F. C.; Boens, N.; J. Chem. Soc., Perkin Trans. 2 1999, 8, 1739-1748.
31. Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction. Org. React. 1997, 50, 1-652.
32. Campbell, I. B. Sonogashira Cu-Pd-catalysed alkyne coupling reaction. In Organocopper reagents: a practical approach; Taylor, R. J. K., Ed.; Oxford University Press: Oxford, 1994; pp 217-235.
33. Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575-5580.
34. Marty, M.; Clyde-Watson, Z.; Twyman, L. J.; Nakash, M.; Sanders, J. K. M. Chem. Commun. 1998, 2265-2266.
35. Gowenlock, B. G.; Cameron, M.; Boyd, A. S. F. J. Chem. Res. Synth. 1995, 358-359.
36. Teixidor, F.; Angles, P.; Vinas, C.; Kivekas, R.; Sillanpaa, R. Inorg. Chem. 2001, 40, 4010-4015.
37. Ochiai, E. J. Org. Chem. 1953, 18, 4-551.
38. Lamture, J. B.; Zhou, Z. H.; Kumar, A. S.; Wensel, T. G. Inorg. Chem. 1995, 34, 864-869.
39. Guillier, F.; Nivoliers, F.; Godard, A.; Marsais, F.; Queguiner, G.; Siddiqui, M. A.; Snieckus, V. J. Org. Chem. 1995, 60, 292-296.