Synthesis and characterization of new triazenide salts

Journal of Organic Chemistry

Volumn 71, Issue 10, 2006, Pages 4014-4017

  Virag, Andrej ^a   Meden, Anton ^a   Kočevar, Marijan ^a   Polanc, Slovenko ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; ESTERIFICATION; SYNTHESIS (CHEMICAL);

TRANSESTERIFICATIONS; TRIAZENES; TRIETHYLAMINES;

SALTS;

AMMONIUM DERIVATIVE; CARBONYLVINYLTRIETHYLAMMONIUM TRIAZENIDE; TRIAZENE DERIVATIVE; TRIAZENIDE SALT; TRIETHYLAMINE; TRIETHYLAMMONIUM TRIAZENIDE SALT; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; REACTION ANALYSIS; SYNTHESIS; TRANSESTERIFICATION;

EID: 33646523389     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060178p     Document Type: Article

References (31)

1. Kimball, D. B.; Haley, M. M. Angew. Chem., Int. Ed. 2002, 41, 3338-3351.
2. Hill, D. T.; Stanley, K. G.; Williams, J. E. K.; Loev, B.; Fowler, P. J.; McCafferty, J. P.; Macko, E.; Berkoff, C. E.; Ladd, C. B. J. Med. Chem. 1983, 26, 865-869.
3. (a) Brahimi, F.; Rachid, Z.; McNamee, J. P.; Alaoui-Jamali, M. A.; Tari, A. M.; Jean-Claude, B. J. Biochem. Pharmacol. 2005, 70, 511-519.
4. (b) Jean-Claude, B. J.; Mustafa, A.; Damian, Z.; De Marte, J.; Vasilescu, D. E.; Yen, R.; Chan T. H.; Leyland-Jones, B. Biochem. Pharmacol. 1999, 57, 753-762.
5. Nicolaou, K. C.; Boddy, C. N. C.; Li, H.; Koumbis, A. E.; Hughes, R.; Natarajan, S.; Jain, N. F.; Ramanjulu, J. M.; Bräse, S.; Solomon, M. E. Chem.-Eur. J. 1999, 5, 2602-2621.
6. For recent references, see: (a) Knochel, P.; Liu, C. Y. Org. Lett. 2005, 7, 2543-2546.
7. (b) Kimball, D. B.; Weakley, T. J. R.; Herges, R.; Haley, M. M.; J. Am. Chem. Soc. 2002, 124, 13463-13473.
8. (c) Kimball, D. B.; Weakley, T. J. R.; Haley, M. M. J. Org. Chem. 2002, 67, 6395-6405.
9. Bräse, S. Acc. Chem. Res. 2004, 37, 805-816.
10. (a) Martelanc, M.; Kranjc, K.; Polanc, S.; Kočevar, M. Green Chem. 2005, 7, 737-741.
11. (b) Požgan, F.; Polanc, S.; Kočevar, M. Synthesis 2003, 2349-2352.
12. (a) Bombek, S.; Požgan, F.; Kočevar, M.; Polanc, S. New J. Chem. 2005, 29, 948-954.
13. (b) Polanc, S. J. Heterocycl. Chem. 2005, 42, 401-412.
14. (c) Bombek, S.; Požgan, F.; Kočevar, M.; Polanc, S. J. Org. Chem. 2004, 69, 2224-2227.
15. (d) Štefane, B.; Polanc, S. Synlett 2004, 698-702.
16. (e) Čimbora-Zovko, T.; Bombek, S.; Košmrlj, J.; Kovačič, L.; Polanc, S.; Katalinić, A.; Osmak, M. Drug Dev. Res. 2004, 61, 95-100.
17. (f) Vraničar, L.; Polanc, S.; Kočevar, M. Heterocycles 2003, 61, 105-112.
18. (g) Bombek, S.; Lenaršič, R.; Kočevar, M.; Saint-Jalmes, L.; Desmurs, J.-R.; Polanc, S. Chem. Commun. 2002, 1494-1495.
19. Štefane, B.; Kočevar, M.; Polanc, S. J. Org. Chem. 1997, 62, 7165-7169.
20. Štefane, B.; Černigoj, U.; Kočevar, M.; Polanc, S. Tetrahedron Lett. 2001, 42, 6659-6662.
21. McGarrity, J. F. J. Chem. Soc., Chem. Commun. 1974, 558-559.
22. Westhusin, S.; Gantzel, P.; Walsh, P. J. Inorg. Chem. 1998, 37, 5956-5959.
23. Jung, M. E.; Buszek, K. R. J. Am. Chem. Soc. 1988, 110, 3965-3969.
24. McCulloch, A. W.; McInnes, A. G. Can. J. Chem. 1974, 52, 3569-3576.
25. These esters are promoters for some other transesterifications. Namely, several alkyl 4-nitrobenzoates can be successfully transformed into methyl 4-nitrobenzoate at room temperature in a methanolic solution in the presence of 10 mol % of the ester 4c. The reactions are supposed to proceed via N-acyltriazene, which is similar to II (acyl = 4-nitrobenzoyl, X = Br). Unpublished results from our laboratory.
26. Collect; Nonius, BV: Delft, The Netherlands, 1998.
27. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326.
28. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Cryst. 1999, 32, 115-119.
29. Hall, S. R.; King, G. S. D.; Stewart, J. M. The Xtal3.4 User's Manual; University of Western Australia: Lamb, Perth, 1995.
30. Burnett, M. N.; Johnson, C. K. ORTEP-III: Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations; Report ORNL-6895; Oak Ridge National Laboratory: Oak Ridge, TN, 1996.
31. Wang, H.; Robertson, B. E. In Structure and Statistics in Crystallography; Wilson, A. J. C., Ed.; Adenine Press: New York, 1985; pp 125-136.