SHORT PAPER
Novel Synthetic Approaches to (Trifluoromethyl)triazoles
1077
hood!), the product was dissolved in CH Cl (300 mL) to remove all
insoluble materials. The solution was evaporated under vacuum and
the thus-formed tarry residue was purified by double sublimation
(4) (a) Arban, R.; Benedetti, R.; Bonanomi, G.; Capelli, A.-M.;
Castiglioni, E.; Contini, S.; Degiorgis, F.; Di Felice, P.;
Donati, D.; Fazzolari, E.; Gentile, G.; Marchionni, C.;
Marchioro, C.; Messina, F.; Micheli, F.; Oliosi, B.; Pavone,
F.; Pasquarello, A.; Perini, B.; Rinaldi, M.; Sabbatini, F. M.;
Vitulli, G.; Zarantonello, P.; Di Fabio, R.; St-Denis, Y.
ChemMedChem 2007, 2, 528. (b) Hager, C.; Miethchen, R.;
Reinke, H. J. Fluorine Chem. 2000, 104, 135.
2
2
(
20 mmHg, ∼80–90 °C) to give 2 (30.3 g, 221 mmol, 64%) as a
white solid.
Mp 79–80 °C.
1
H NMR (500 MHz, CDCl ): d = 8.95–8.20 (2 × br s, NH + CH).
3
1
3
(c) Stepanova, N. P.; Orlova, N. A.; Galishev, V. A.;
Turbanova, E. S.; Petrov, A. A. Zh. Org. Khim. 1985, 21,
C NMR (125 MHz, CDCl ): d = 137.21 (br s), 124.15 (br s),
3
1
1
21.71 (q, J = 267.7 Hz, CF3).
C,F
979. (d) Stepanova, N. P.; Galishev, V. A.; Turbanova, E. S.;
1
9
F NMR (470 MHz, CDCl ): d = –61.55 (s, CF ).
3
3
Maleev, A. V.; Potehin, K. A.; Kurkutova, E. N.; Struchkov,
Y. T.; Petrov, A. A. Zh. Org. Khim. 1989, 25, 1613.
MS: m/z = 137 [M+].
(
(
(
(
5) Evans, J. J. A.; Holan, G. US 4038405, 1977; Chem. Abstr.
1977, 87, 168041.
References
6) Crossman, J. M.; Haszeldine, R. N.; Tipping, A. E. J. Chem.
Soc., Dalton Trans. 1973, 483.
7) Ye, C.; Gard, G. L.; Winter, R. W.; Syvret, R. G.; Twamley,
B.; Shreeve, J. M. Org. Lett. 2007, 9, 3841.
8) Bandera, Y. P.; Kanishchev, O. S.; Timoshenko, V. M.; But,
S. A.; Nesterenko, A. M.; Shermolovich, Y. G. Chem.
Heterocycl. Compd. (Engl. Transl.) 2007, 43, 1138.
9) Dmowski, W. In Houben–Weyl Methods of Organic
Chemistry, Vol. E 10a; Baasner, B.; Hagemann, H.; Tatlow,
J. C., Eds.; Georg Thieme: Stuttgart, 1999, 321.
(
1) Krivopalov, V. P.; Shkurko, O. P. Russ. Chem. Rev. (Engl.
Transl.) 2005, 74, 339.
2) (a) Awad, L. F.; El Ashry, S. H. Carbohydr. Res. 1998, 312,
(
9. (b) Amir, M.; Shikha, K. Eur. J. Med. Chem. 2004, 39,
535. (c) Palaska, E.; Sahin, G.; Kelicen, P.; Durlu, N. T.;
Altinok, G. Farmaco 2002, 57, 101. (d) Holla, B. S.;
Poorjary, K. N.; Rao, B. S.; Shivananda, M. K. Eur. J. Med.
Chem. 2002, 37, 511. (e) Henichart, J. P.; Houssin, R.;
Berier, J. L. J. Heterocycl. Chem. 1986, 23, 1531.
(
(
10) Sternfeld, F.; Carling, R. W.; Jelley, R. A.; Ladduwahetty,
T.; Merchant, K. J.; Moore, K. W.; Reeve, A. J.; Street, L. J.;
O’Connor, D.; Sohal, B.; Atack, J. R.; Cook, S.; Seabrook,
G.; Wafford, K.; Tattersall, F. D.; Collinson, N.; Dawson, G.
R.; Castro, J. L.; MacLeod, A. M. J. Med. Chem. 2004, 47,
(
f) Demirbas, N.; Karaoglu, S. A.; Demirbas, A.; Sancak, K.
Eur. J. Med. Chem. 2004, 39, 793. (g) Demirbas, N.;
Demirbas, A.; Karaoglu, S. A. Russ. J. Bioorg. Chem. (Engl.
Transl.) 2005, 31, 387.
(
3) (a) O’Hagan, D.; Rzepa, H. S. Chem. Commun. 1997, 645.
2176.
(
b) Kirsch, P. Modern Fluoroorganic Chemistry; Wiley-
VCH: Weinheim, 2004. (c) Qiu, X.-L.; Meng, W.-D.; Qing,
F.-L. Tetrahedron 2004, 60, 6711.
Synthesis 2010, No. 7, 1075–1077 © Thieme Stuttgart · New York