1938
W. J. Peláez et al. / Tetrahedron Letters 50 (2009) 1934–1938
α
H
HN
N
H
OH
2 H
-H2O
5
N
N
N
N
H
F3C
H
F3C
15
CF3
NH
15I
16I
-2
HN
2
OH
H
H
N
H
N
N
H
N
F3C
F3C
16
11
Scheme 4. Reaction of formation of 16.
5. Qiu, X. L.; Meng, W.-D.; Qing, F.-L. Tetrahedron 2004, 60, 6711–6745.
6. Alumni, S.; Clementi, S. J. Chem. Soc., Perkin Trans. 2 1972, 1521–1525.
7. Clementi, S.; Marino, G. J. Chem. Soc., Perkin Trans. 2 1972, 71–73.
8. Clementi, S.; Marino, G. Tetrahedron 1969, 25, 4599–4603.
9. Montiel-Smith, S.; Meza-Reyes, S.; Viñas-Bravo, O.; Fernandéz-Herrera, M. A.;
Martínez-Pascual, R.; Sandoval-Ramirez, J.; Fuente, A.; Reyes, M.; Ruiz, J. A.
ARKIVOC 2005, vi, 127–135.
This work has shown that new compounds could be obtained
with some changes in the conditions of an old reaction. This opens
new ways (since the yields so far obtained are relatively low, re-
newed efforts will be put in their study) to synthesize compounds
bearing fluorinated groups.
10. Hong, S.-J.; Jeong, S.-D.; Yoo, J.; Kim, J. S.; Yoon, J.; Lee, C.-H. Tetrahedron Lett.
2008, 49, 4138–4141.
Acknowledgments
11. Hong, S.-J.; Lee, M.-H.; Lee, C.-H. Bull. Korean Chem. Soc. 2004, 25, 1545–
1550.
12. Reger, D. K.; Grattan, T. C. Synthesis 2003, 3, 350–356.
13. Bhambri, S.; Tocher, D. A. J. Chem. Soc. Dalton Trans. 1997, 3367–3372.
14. Danil de Namor, A. F.; Abbas, I. J. Phys. Chem. B 2007, 111, 5803–5810.
15. Danil de Namor, A. F.; Abbas, I.; Hammud, H. H. J. Phys. Chem. B 2006, 110,
2142–2149.
16. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.;
Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J.
C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi,
M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara,
M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda,
Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross,
J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.;
Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.;
Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V.
G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.;. Farkas, O; Malick, D. K.;
Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul,
A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.;
Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.;
Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.;
Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. GAUSSIAN 03, Revision B.02;
Gaussian: Pittsburgh, PA, 2003.
Financial support from CONICET and SeCyT-UNC is gratefully
acknowledged. W.J.P. wants to thank CONICET for the fellowship
granted.
Supplementary data
Synthetic procedures, characterization and calculated data from
GAUSSIAN03 of compound 10, 11, 12, 13, 14, and 16 are provided.
Supplementary data associated with this article can be found, in
References and notes
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