Activation of urea as a leaving group in substitution reactions of formamidine ureas

Chemistry Letters

Volumn 34, Issue 1, 2005, Pages 78-79

  Díaz, David D ^a   Lewis, Warren G ^a   Finn, M G ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; FORMAMIDINE; PROTON; UREA;

ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 17144391895     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2005.78     Document Type: Article

References (10)

1. A. S. Ripka, D. Díaz, K. B. Sharpless, and M. G. Finn, Org. Lett., 5, 1531 (2003).
2. D. Díaz and M. G. Finn, Chem. - Eur. J., 10, 303 (2004).
3. D. Díaz and M. G. Finn, Org. Lett., 6, 43 (2004).
4. a) D. Díaz and M. G. Finn, Chem. Commun., 2004, 2514, and references therein,
5. b) For other examples of fragment exchange in amidine electrophiles, see: D. M. Vyas, Y. Chiang, D. Benigni, and T. W. Doyle, J. Org. Chem., 52, 5601 (1987); S. Delarue, S. Girault, F. D. Ali, L. Maes, P. Grellier, and C. Sergheraert, Chem. Pharm. Bull., 49, 933 (2001); A. Donetti, E. Cereda, E. Bellora, A. Gallazzi, C. Bazzano, P. Vanoni, P. Del Soldato, R. Micheletti, F. Pagani, and A. Giachetti, J. Med. Chem., 27, 380 (1984).
6. b) For other examples of fragment exchange in amidine electrophiles, see: D. M. Vyas, Y. Chiang, D. Benigni, and T. W. Doyle, J. Org. Chem., 52, 5601 (1987); S. Delarue, S. Girault, F. D. Ali, L. Maes, P. Grellier, and C. Sergheraert, Chem. Pharm. Bull., 49, 933 (2001); A. Donetti, E. Cereda, E. Bellora, A. Gallazzi, C. Bazzano, P. Vanoni, P. Del Soldato, R. Micheletti, F. Pagani, and A. Giachetti, J. Med. Chem., 27, 380 (1984).
7. b) For other examples of fragment exchange in amidine electrophiles, see: D. M. Vyas, Y. Chiang, D. Benigni, and T. W. Doyle, J. Org. Chem., 52, 5601 (1987); S. Delarue, S. Girault, F. D. Ali, L. Maes, P. Grellier, and C. Sergheraert, Chem. Pharm. Bull., 49, 933 (2001); A. Donetti, E. Cereda, E. Bellora, A. Gallazzi, C. Bazzano, P. Vanoni, P. Del Soldato, R. Micheletti, F. Pagani, and A. Giachetti, J. Med. Chem., 27, 380 (1984).
8. Compound 3 was prepared independently by sequential treatment of N,N-dimethylformamide dimethylacetal with tert-butyl and benzyl amines, or from the commercially available dimethyl-tert-butyl formamidine intermediate.
9. 2O, and ionization current at a relatively low setting of 60. Product mixtures were invariant to storage in this solvent system for at least 15-30 min, which exceeds the duration of the EIMS analyses. Upon exposure to aqueous mixtures for longer periods, hydrolysis of formamidine ureas and, to a much lesser extent, formamidines, becomes evident.
10. M. Decouzon, J.-F. Gal, P.-C. Maria, and E. D. Raczynska, Org. Mass Spectrom., 92, 1127 (1991).