Increasing the N-H acidity: Introduction of highly electronegative groups into the hydrazine molecule

Synlett

Volumn , Issue 12, 2005, Pages 1939-1941

  Bredikhin, Aleksei ^a   Tšubrik, Olga ^a   Sillard, Rannar ^b   Mäeorg, Uno ^a  

^a UNIVERSITY OF TARTU   (Estonia)

^b KAROLINSKA INSTITUTE   (Sweden)

Author keywords

Acylations; Hydrazines; Neighboring group effects; Protecting groups; Sulfonamides

Indexed keywords

2,4 DINITROPHENOL; HYDRAZINE; TRIFLUOROACETIC ACID; TRIFLUOROMETHANESULFONIC ACID;

ACIDITY; ACYLATION; ALKYLATION; ARTICLE; OXIDATION; PROTON TRANSPORT; SUBSTITUTION REACTION; SYNTHESIS;

EID: 23644449679     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-871928     Document Type: Article

References (26)

1. For a review see: Ragnarsson, U. Chem. Soc. Rev. 2001, 30, 205; and references therein.
2. (a) Mäeorg, U.; Grehn, L.; Ragnarsson, U. Angew. Chem., Int. Ed. Engl. 1996, 35, 2626.
3. (b) Brosse, N.; Jamart-Gregoire, B. Tetrahedron Lett. 2002, 43, 249.
4. (c) Tsubrik, O.; Mäeorg, U. Org. Lett. 2001, 3, 2297.
5. (d) Tšubrik, O.; Mäeorg, U.; Sillard, R.; Ragnarsson, U. Tetrahedron 2004, 60, 8363.
6. (a) Brosse, N.; Pinto, M.-F.; Jamart-Gregoire, B. J. Org. Chem. 2000, 65, 4370.
7. (b) Brosse, N.; Pinto, M.-F.; Jamart-Gregoire, B. J. Chem. Soc., Perkin Trans, 1 1998, 3685.
8. (c) Young, J. A.; Durrell, W. S.; Dresdner, R. D. J. Am. Chem. Soc. 1962, 84, 2105.
9. (a) Ye, F.; Noftle, R. E. J. Fluorine Chem. 1997, 81, 193.
10. (b) Narula, P. M.; Day, C. S.; Powers, B. A.; Odian, M. A.; Lachgar, A.; Pennington, W. T.; Noftle, R. E. Polyhedron 1999, 18, 1751.
11. (a) Mattioni, B. E.; Jurs, P. C. J. Chem. Inf. Comput. Sci. 2002, 42, 94.
12. (b) Scozzafava, A.; Menabuoni, L.; Mincione, F.; Briganti, F.; Mincione, G.; Supuran, C. T. J. Med. Chem. 2000, 43, 4542.
13. (c) Mcmahon, E. G.; Olins, G. M.; Schuh, J. R. PCT Int. Appl. WO 9640256, 1996.
14. Ding, H.; Friestad, G. Org. Lett. 2004, 6, 637.
15. Koppel, I.; Koppel, J.; Degerbeck, F.; Grehn, L.; Ragnarsson, U. J. Org. Chem. 1991, 56, 7172.
16. Ragnarsson, U.; Grehn, L.; Koppel, J.; Loog, O.; Tšubrik, O.; Bredikhin, A.; Mäeorg, U.; Koppel, I. J. Org. Chem. 2005, in press.
17. (a) Groth, R. H. J. Org. Chem. 1959, 25, 102.
18. (b) Brown, H. C.; Cheng, M. T.; Parcell, L. J.; Pilipovich, D. J. Org. Chem. 1961, 26, 4407.
19. Braun, M. W.; Rudolph, W. H.; Palsherm, S. B.; Eichholz, K. L. US Patent 5532411, 1996.
20. 2N].
21. Ried, W.; Franz, G. Liebigs Ann. Chem. 1961, 644, 141.
22. Fritz, H.; Kristinsson, H.; Mollenkopf, M.; Winkler, T. Magn. Res. Chem. 1990, 28, 331.
23. -].
24. Schreiber, S. L. Tetrahedron Lett. 1980, 21, 1027.
25. -].
26. Hendrickson, J. B.; Sternbach, D. D. J. Org. Chem. 1975, 40, 3450.