2
284
Synthesis
Y. Yang, C. Kuang
Paper
1
H NMR (400 MHz, CDCl ): δ = 6.57 (t, J = 2.2 Hz, 1 H), 7.67 (t, J =
.2 Hz, 1 H), 7.80 (d, J = 1.2 Hz, 1 H), 8.05 (d, J = 2.4 Hz, 1 H), 8.09–8.18
(6) (a) Penning, T. D.; Talley, J. J.; Bertenshaw, S. R.; Carter, J. S.;
Collins, P. W.; Docter, S.; Graneto, M. J.; Lee, L. F.; Malecha, J. W.;
Miyashiro, J. M.; Rogers, R. S.; Rogier, D. J.; Yu, S. S.; Anderson, G.
D.; Burton, E. G.; Cogburn, J. N.; Gregory, S. A.; Koboldt, C. M.;
Perkins, W. E.; Seibert, K.; Veenhuizen, A. W.; Zhang, Y. Y.;
Isakson, P. C. J. Med. Chem. 1997, 40, 1347. (b) Kujubu, D. A.;
Fletcher, B. S.; Varnum, B. C.; Lim, R. W.; Herschman, H. R. J. Biol.
Chem. 1991, 266, 12866.
3
8
(m, 2 H), 8.58 (t, J = 2.0 Hz, 1 H).
4
,5-Dihydro-1-p-tolyl-1H-pyrazole (4a)
Prepared by following the general procedure (K S O was not used).
2
2
8
Yield: 43 mg (0.270 mmol, 90%); tan solid; mp 51.5–52.6 °C.
IR (KBr): 3042, 2962, 2848, 1659, 1572, 1549, 1529, 1467, 1384, 1280,
(7) Sun, X.; Tian, J.; Zhu, M.; Chai, B.; Liu, C. Agrochemicals 2011, 50,
781.
–1
815 cm .
1
(8) (a) Taillefer, M.; Xia, N.; Ouali, A. Angew. Chem. Int. Ed. 2007, 46,
H NMR (400 MHz, CDCl ): δ = 2.31 (s, 3 H), 2.87–2.98 (m, 2 H), 3.65
3
934. (b) Correa, A.; Bolma, C. Adv. Synth. Catal. 2007, 349, 2673.
(t, J = 10.2 Hz, 2 H), 6.85 (s, 1 H), 6.98 (d, J = 8.4 Hz, 2 H), 7.11 (d, J =
(c) Chen, W.; Zhang, Y.; Zhu, L.; Lan, J.; Xie, R.; You, J. J. Am.
8
.4 Hz, 2 H).
Chem. Soc. 2007, 129, 13879. (d) Suresh, P.; Pitchumani, K. J. Org.
Chem. 2008, 73, 9121. (e) Guo, D.; Huang, H.; Xu, J.; Jiang, H.;
Liu, H. Org. Lett. 2008, 10, 4513. (f) Kaddouri, H.; Vicente, V.;
Ouali, A.; Ouazzani, F.; Taillefer, M. Angew. Chem. Int. Ed. 2009,
48, 333. (g) Larsson, P.; Correa, A.; Carril, M.; Norrby, P.; Bolm, C.
Angew. Chem. Int. Ed. 2009, 48, 5691. (h) Swapna, K.; Kumar, A.
V.; Reddy, V. P.; Rao, K. R. J. Org. Chem. 2009, 74, 7514.
(i) Murthy, S. N.; Madhav, B.; Reddy, V. P.; Nageswar, Y. V. D. Adv.
Synth. Catal. 2010, 352, 3241. (j) Cano, R.; Ramon, D. J.; Yus, M.
J. Org. Chem. 2011, 76, 654. (k) Yang, K.; Qiu, Y.; Li, Z.; Wang, Z.;
Jiang, S. J. Org. Chem. 2011, 76, 3151. (l) Huang, Z.; Li, F.; Chen,
B.; Xue, F.; Chen, G.; Yuan, G. Appl. Catal., A 2011, 403, 104.
(m) Cristau, H.; Cellier, P. P.; Spindler, J.; Taillefer, M. Chem. Eur.
J. 2004, 10, 5607.
1
3
C NMR (100 MHz, CDCl ): δ = 20.5, 33.5, 47.1, 113.2 (2C), 128.5,
3
1
29.6 (2C), 140.7, 144.5.
HRMS (ESI): m/z [M + H]+ calcd for C10H13N : 161.1073; found:
1
2
61.1070.
Acknowledgment
The work was supported by the Natural Science Foundation of China
(
(
No. 21272174), the Key Projects of Shanghai in Biomedical
No.08431902700), and the Scientific Research Foundation of State
Education Ministry for the Returned Overseas Chinese Scholars. We
would like to thank the Center for Instrumental Analysis, Tongji Uni-
versity, P. R. of China.
(9) (a) Finar, I. L.; Godfrey, K. E. J. Chem. Soc. 1954, 2293. (b) Guo, C.;
Ren, T.; Wang, J.; Li, C.; Song, J. J. Porphyrins Phthalocyanines
2
005, 9, 430. (c) Ju, Y.; Varma, R. S. J. Org. Chem. 2006, 71, 135.
Supporting Information
(10) Patel, H. V.; Vyas, K. A.; Pandey, S. P.; Tavares, F.; Fernandes, P. S.
Synlett 1991, 483.
11) (a) Huisgen, R.; Gotthardt, H.; Grashey, R. Chem. Ber. 1968, 101,
Supporting information for this article is available online at
(
http://dx.doi.org/10.1055/s-34-1380658.
S
u
p
p
ortioIgnfrm oaitn
S
u
p
p
ortioIgnfrm oaitn
5
36. (b) Huisgen, R.; Grashey, R.; Gotthardt, H. Chem. Ber. 1968,
101, 829.
(
12) (a) Gonzalez-Nogal, A. M.; Calle, M.; Cuadrado, P.; Valero, R. Tet-
rahedron 2007, 63, 224. (b) Browne, D. L.; Vivat, J. F.; Plant, A.;
Gomez-Bengoa, E.; Harrity, J. P. A. J. Am. Chem. Soc. 2009, 131,
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©
Georg Thieme Verlag Stuttgart · New York — Synthesis 2015, 47, 2281–2284