4
Tetrahedron Letters
Experimental
Dombroski, M. A.; Letavic, M. A. Biopharm. Drug
Dispos. 2006, 27, 371; (d) Luethy, C.; Hall, R. G.;
Edmunds, A.; Riley, S.; Diggelmann, M. PCT Int.
Appl. WO08006540, 2008; (e) Abel, U.; Deppe, H.;
Feurer, A.; Gradler, U.; Ott, I.; Matassa, V. G. PCT Int.
Appl. WO06058752, 2006; (f) Reichelt, A.; Falsey, J.
R.; Rzasa, R. M.; Oliver, R. T.; Achmatowicz, M. M.;
Larsen, R. D.; Zhang, D. Org. Lett. 2010, 12, 792; (g)
Rutgeerts, P.; DHaens, G.; Targan, S.; Vasiliauskas, E.;
Hanauer, S. B.; Present, D. H.; Mayer, L.; Hogezand,
R. A. V.; Braakman, T.; DeWoody, K. L.; Shaible, T.
F.; Deventer, S. J. H. V. Gastroenterology, 1999, 117,
General procedure
An oven-dried 20 mL sealed tube under N
2
containing
arylidenehydrazinylpyridine (0.1 mmol), RuCl
), Oxone (0.3 mmol) and 2 mL 1,2-dichloroethane.
a
stir bar was charged with 2-
3
(5 mol
%
o
The reaction mixture was stirred at 70 C for 2 h. When
the reaction was completed as observed by TLC, the
mixture was diluted with water (15 mL) and extracted
with EtOAc (4 x 15 mL), dried over anhydrous Na
and evaporated under reduced pressure. Crude products
were purified by column chromatography on silica gel
2
SO
4
7
61; (h) Ulfgren, A. K.; Andersson, U.; Engstrom, M.;
Klareskog, L.; Maini, R. N.; Taylor, P. C. Arthritis
Rheum. 2000, 43, 2391.
(
DCM/MeOH: 95/5) to afford the desired products.
2 (a) Dombroski, M. A.; Letavic, M. A.; McClure, K. F.
U.S. Pat. Appl. Publ. 2004077682; (b) Buzon, R. A.;
Castaldi, M. J.; Li, Z. B.; Ripin, D. H. B.; Tao, Y.
PCT Int. Appl. 2004020438; (c) Jerome, K. D.; Rucker,
P. V.; Xing, L.; Shieh, H. S.; Baldus, J. E.; Selness, S.
R.; Letavic, M. A.; Braganza, J. F.; McClure, K. F.
Bioorganic & Medicinal Chemistry Letters, 2010, 20,
Supporting Information Available
Detailed procedures and spectroscopic data for novel
compounds, copies of HNMR, CNMR of novel
compounds prepared are available.
1
13
4
69. (d) Foster, M. L.; Halley, F.; Souness, J. E. Drug
In conclusion, we have developed an efficient procedure
News Perspect. 2000, 13, 488; (e) Lee, J. C.; Laydon, J.
T.; McDonnell, P. C.; Gallagher, T. F.; Kumar, S.;
Green, D.; MeNulty, D.; Blumenthal, M. J.; Heys, J. R.;
Landvatter, S. W.; Strickler, J. E.; McLaughlin, M. M.;
Siemens, I. R.; Fisher, S. M.; Livi, G. P.; White, J. R.;
Adams, J. L.; Young, P. R. Nature, 1994, 372, 739.
Yu, G., Li, J.; Ewing, W. R.; Sulsky, R. B.; Li, J. J.;
Tino, J. A. PCT Int. Appl. 2004021984.
for
arylidenehydrazinyl)pyridines
corresponding
derivatives. The reaction proceeds through an oxidative
C-N bond formation. The use of RuCl /Oxone provides
the desired products under operationally simple and
convenient conditions with improved yields and
enhanced reaction rates.
the
oxidative
cyclization
of
2-(2-
the
to
afford
3-aryl-[1,2,4]triazolo[4,3-a]pyridine
3
3
4
Zimmermann, P. J.; Brehm, C.; Palmer, A.; Chiesa, M.
V.; Simon, W. A.; Postius, S.; Kromer, W.; Buhr, W.
PCT Int. Appl. 2005077947.
5
6
7
8
Lawson, E. C.; Maryanoff, B. E.; Hoekstra, W. J.
Tetrahedron Lett. 2000, 41, 4533.
Oliver, R. T.; Michal, M. A.; Reichelt, A.; Larsen, R.
D. Angew. Chem. Int. Ed. 2010, 49, 8395.
Moulin, A.; Martinez, J.; Fehrentz, J. A. Tetrahedron
Lett. 2006, 47, 7591.
Ciesielski, M.; Pufky, D.; Doring, M. Tetrahedron,
2005, 61, 5942.
Acknowledgements
T. Swamy thanks to DST-SERB (File no: SB/FT/CS-
0
48/2013), India for a Research Grant and fellowship.
Supplementary data
Experimental details, characterization data, copies of H
1
1
3
9 Jie, W.; Qiulin, Y.; Jingbo, L.; Qiang, G.; Xiaoyu, L.;
Ying, X., Jingsong, Y. Org. Biomol. Chem. 2015, 13,
5372.
and C NMR spectrum of products can be found, in the
References and Notes
1
0 Anil, K. S.; Yasmin, M.; Kamal, R. A.; Prakash, O.
European Journal of Medicinal Chemistry, 2003, 38,
533.
1
(a) Yoshimura, K.; Tomimatsu, K.; Nishimura, T.;
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11 Schmidt, M. A.; Qian, X. Tetrahedron Lett. 2013, 54,
5721.
(
b) Lawson, E. C.; Hoekstra, W. J.; Addo, M. F.;
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925. (b) Gibson, M. S. Tetrahedron, 1963, 19, 1587.
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