Direct N-Arylation of Azaheterocycles with Aryl Halides under Ligand-free Condition
Chem. Soc. 2005, 127, 9948; (d) Lakshmi Kantam, M.; Venkanna, G.
120, 104, 77.
1-(4-Nitrophenyl)-1H-benzimidazole[2c] (Table 3,
T.; Sridhar, C. Tetrahedron Lett. 2006, 47, 3897; (e) Lv, X.; Wang,
Z.-M.; Bao, W.-L. Tetrahedron 2006, 62, 4756; (f) Chen, W.; Zhang,
Y.; Zhu, L.; Lan, J.; Xie, R.;You, J. J. Am. Chem. Soc. 2007, 129,
13879; (g) Yan, J.-C.; Zhou, L.; Wang, L. Chin. J. Chem. 2008, 26,
165; (h) Maheswaran, H.; Krishna, G. G.; Prasanth, K. L.; Srinivas,
V.; Krishna, C. G.; Bhanuprakash, K. Tetrahedron 2008, 64, 2471;
(i) Wu, X.-M.; Wang, Y. Chin. Chem. Lett. 2010, 21, 51; (j) Yang,
X.-Y.; Xing, H.; Zhang, Y.; Lai, Y.-S.; Zhang, Y.-H.; Jiang, Y.-W.;
Ma, D.-W. Chin. J. Chem. 2012, 30, 875.
1
Entry 6). Yellow solid; m.p. 180—182 ℃; H NMR
(400 MHz, CDCl3) δ: 7.33—7.41 (m, 2H), 7.56—7.60
(m, 1H), 7.76 (d, J=8.9 Hz, 2H), 7.84—7.89 (m, 1H),
8.14 (s, 1H), 8.47 (d, J=8.9 Hz, 2H); IR (KBr) νmax
2926, 1652, 1603, 1521, 1444, 1273, 1151, 1056, 934,
:
-
1
856, 736, 699 cm . MS (EI) m/z (%): 239 (100), 209,
192, 167, 141.
[3] (a) Parrish, C. A.; Buchwald, S. L. J. Org. Chem. 2001, 66, 3820; (b)
Urgaonkar, S.; Nagarajan, M.; Verkade, J. G. J. Org. Chem. 2003,
68, 452; (c) Xie, X.; Zhang, T.-Y.; Zhang, Z. J. Org. Chem. 2006, 71,
6522.
[4] (a) Correa, A.; Bolm, C. Angew. Chem., Int. Ed. 2007, 46, 8862; (b)
Guo, D.-L.; Huang, H.; Xu, J.; Jiang, H.-L.; Liu, H. Org. Lett. 2008,
10, 4513; (c) Swapna, K.; Vijay Kumar, A.; Prakash Reddy, V.;
Rama Rao, K. J. Org. Chem. 2009, 74, 7514; (d) Lee, H.-W.; Chan,
A. S. C.; Kwong, F.-Y. Tetrahedron Lett. 2009, 50, 5868; (e) Teo,
Y.-C. Adv. Synth. Catal. 2009, 351, 720.
[5] (a) Cristau, H. J.; Cellier, P. P.; Spindler, J. F.; Taillefer, M. Chem.
Eur. J. 2004, 10, 5607; (b) Oshovsky, G. V.; Ouali, A.; Xia, N.;
Zablocka, M.; Boeré, R. T.; Duhayon, C.; Taillefer, M.; Majoral, J.
P. Organometallics 2008, 27, 5733; (c) Monnier, F.; Taillefer, M.
Angew. Chem., Int. Ed. 2009, 48, 6954.
1-(2-Nitrophenyl)-1H-pyrazole[16] (Table 3, Entry
1
7). Yellowish solid; m.p. 86—88 ℃; H NMR (400
MHz, CDCl3) δ: 6.53 (d, J=2.5 Hz, 1H), 7.50—7.70 (m,
3H), 7.56—7.72 (m, 1H), 7.77 (d, J=2.5 Hz, 1H), 7.89
(d, J=7.2 Hz, 1H); IR (KBr) νmax: 3047, 2083, 1739,
-
1
1610, 1532, 1365, 1044, 936, 766, 615, 538 cm . MS
(EI) m/z (%): 189, 159, 132 (100), 89, 77.
1-(2-Nitrophenyl)-1H-imidazole[6c] (Table 3, En-
1
try 8). Yellow solid; m.p. 95—97 ℃; H NMR (400
MHz, CDCl3) δ: 7.10—7.18 (m, 1H), 7.23 (s, 1H), 7.37
(d, J=7.5 Hz, 1H), 7.47—7.53 (m, 2H), 7.64 (d, J=7.5
Hz, 1H), 8.14 (d, J=8.3 Hz, 1H); IR (KBr) νmax: 3103,
-
1
1606, 1523, 1356, 1058, 739, 657 cm . MS (EI) m/z
[6] (a) Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1996, 61, 7240; (b)
Klapars, A.; Antilla, J. C.; Huang, X.-H.; Buchwald, S. L. J. Am.
Chem. Soc. 2001, 123, 7727; (c) Klapars, A.; Huang, X.-H.; Buch-
wald, S. L. J. Am. Chem. Soc. 2002, 124, 7421; (d) Antilla, J. C.;
Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 11684;
(e) Kwang, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4,
581; (f) Job, G. E.; Buchwald, S. L. Org. Lett. 2002, 4, 3703; (g)
Kwang, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793; (h) Engue-
hard, C.; Allouchi, H.; Gueiffier, A.; Buchwald, S. L. J. Org. Chem.
2003, 68, 4367; (i) Antilla, J. C.; Baskin, J. B.; Barder, T. E.; Buch-
wald, S. L. J. Org. Chem. 2004, 69, 5578; (j) Altman, R. A.; Koval,
E. D.; Buchwald, S. L. J. Org. Chem. 2007, 72, 6190.
[7] (a) Teo, Y.-C.; Yong, F.-F.; Poh, C.-Y.; Yan, Y.-K.; Chua, G.-L.
Chem. Commun. 2009, 6258; (b) Yong, F.-F.; Teo, Y.-C.; Tay, S.-H.;
Tan, B.-Y.; Lim, K.-H. Tetrahedron Lett. 2011, 52, 1161; (c) Teo,
Y.-C.; Chua, G.-L. Chem. Eur. J. 2009, 15, 3072.
[8] Chouhan, G.-G.; Wang, D.-S.; Alper, H. Chem. Commun. 2007,
4809.
(%): 89 (100), 159, 142, 116, 89, 63, 50.
1-(2,4-Dinitrophenyl)-1H-imidazole[17] (Table 3,
1
Entry 9). Yellow solid; m.p. 146—149 ℃; H NMR
(400 Hz CDCl3) δ: 6.57 (d, J=5.7 Hz, 1H), 6.91 (s, 1H),
7.71 (d, J=3.4 Hz, 1H), 8.01 (d, J=3.4 Hz, 1H), 8.25
(d, J=5.7 Hz, 1H), 9.13 (s, 1H); IR (KBr) νmax: 3134,
-
1
1606, 1539, 1325, 1129, 914, 834, 743, 654 cm . MS
(EI) m/z (%): 234, 204, 158 (100), 115, 53.
1-(2,4-Dinitrophenyl)-1H-pyrazole[17] (Table 3,
Entry 10). Yellow solid; m.p. 107—109 ℃; 1H NMR
(400 Hz CDCl3) δ: 6.90 (d, J=5.7 Hz, 1H), 7.19 (s, 1H),
7.26 (s, 1H), 8.17 (s, 1H), 8.23 (d, J=5.7 Hz, 1H), 9.12
(s, 1H); IR (KBr) νmax: 3144, 3073, 2924, 2854, 1585,
-
1
1525, 1330, 1130, 1045, 931, 747, 648 cm . MS (EI)
m/z (%): 234, 204, 158 (100), 115, 53.
1-(3-Chlorophenyl)-1H-pyrazole[4a]
(Table 3,
[9] Rao, R. K.; Naidu, A. B.; Jaseer, E. A.; Sekar, G. Tetrahedron 2009,
65, 4619.
[10] Antilla, J. C.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc.
2002, 124, 11684.
[11] Ma, H.-C.; Jiang, X.-Z. J. Org. Chem. 2007, 72, 8943.
[12] Periasamy, M.; Vairaprakash, P.; Dalai, M. Organometallics 2008,
27, 1963.
Entry 11). Yellowish oil; 1H NMR (400 MHz, CDCl3) δ:
6.45—6.46 (m, 1H), 7.24—7.27 (m, 1H), 7.37 (t, J=7.8
Hz, 1H), 7.56—7.60 (m, 1H), 7.73 (d, J=2.4 Hz, 1H),
7.75 (s, 1H), 7.90 (d, J=2.5 Hz, 1H). MS (EI) m/z (%):
178 (100), 151, 111, 89, 75.
[13] Liu, L.-B.; Frohn, M.; Xi, N.; Dominguez, C.; Hungate, R.; Reider,
P. J. J. Org. Chem. 2005, 70, 10135.
Acknowledgement
[14] (a) Lakshmi Kantam, M.; Yadav, J.; Laha, S.; Sreedhar, B.; Jhab, S.
Adv. Synth. Catal. 2007, 349, 1938; (b) Correa, A.; Bolm, C. Adv.
Synth. Catal. 2007, 349, 2673; (c) Sreedhar, B.; Arundhathi, R.;
Linga Reddy, P.; Lakshmi Kantam, M. J. Org. Chem. 2009, 74,
7951; (d) Colacino, E.; Villebrun, L.; Martinez, J.; Lamaty, F. Tet-
rahedron 2010, 66, 3730; (e) Guo, D.-L.; Huang, H.; Zhou, Y.; Xu,
J.-Y.; Jiang, H.-L.; Chen, K.-X.; Liu, H. Green Chem. 2010, 12, 276.
[15] Narayana Murthy, S.; Madhav, B.; Prakash Reddy, V. Y.; Nageswar,
V. D. Adv. Synth. Catal. 2010, 352, 3241.
This work was supported by the National Natural
Science Foundation of China (No. 20802049).
References
[1] (a) Zhong, C.-L.; He, J.-T.; Xue, L.-Y. J. Bioorg. Med. Chem. 2004,
12, 4009; (b) Grauer, A.; Späth, A.; Ma, D.; König, B. Chem. Asian J.
2009, 4, 1134.
[2] (a) Kiyomori, A.; Marcoux, J. F.; Buchwald, S. L. Tetrahedron Lett.
1999, 40, 2657; (b) Cristau, H. J.; Cellier, P. P.; Spindler, J. F.;
Taillefer, M. Eur. J. Org. Chem. 2004, 695; (c) Choudary, B. M.;
Sridhar, C.; Kantam, M. L.; Venkanna, G. T.; Sreedhar, B. J. Am.
[16] Hoz, A.; Diaz-Ortiz, A.; Elguero, J.; Martinez, L.; Moreno, A.;
Sanchez, A. Tetrahedron 2001, 57, 4397.
[17] Zima, V.; Pytela, O.; Kavalek, J.; Vecera, M. Collect. Czech. Chem.
Commun. 1989, 54, 2715.
(Lu, Y.)
Chin. J. Chem. 2012, XX, 1—5
© 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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