1
050
Can. J. Chem. Vol. 86, 2008
1
7
.7 Hz), 7.16–7.20 (4H, m), 7.53 726 (1H, d, J = 3.1 Hz),
.56 (1H, d, J = 3.1 Hz), 7.89 (1H, s). C NMR (DMSO-d6)
Phenyl(2-phenyl-1H-benzimidazol-5-yl)methanone (5s)
1
3
Recrystallization from EtOH/H O (2:1) gave compound
2
δC: 110.6, 112.3, 115.0, 122.3, 138.8, 143.6, 144.6, 145.3.
5s as a pale yellow powder in 85% yield. Mp 221–222 °C
1
(
7
Lit. 221–221.5 °C (30)). H NMR (DMSO-d ) δ : 7.41–
6
H
1
3
.58 (11H, m), 8.19 (2H, d, J = 7.4 Hz), 13.28 (1H, s).
C
2
-(2-Thienyl)-1H-benzimidazole (5m)
Purification by flash column chromatography, eluted with
NMR (DMSO-d ) δ : δ 124.2, 126.7, 128.3, 129.0, 129.4,
6
C
1
29.5, 130.4, 131.0. 132.0, 138.7, 153.9.1, 195.5.
n-hexane/ethyl acetate (7:1), gave compound 5m as a yellow
powder in 87% yield. Mp 329–331 °C (Lit. 330 °C (33)). H
1
NMR (DMSO-d ) δ : 7.16–7.22 (3 H, m), 7.48–7.58 (2H,
6
H
m), 7.73 (1H, d, J = 3.1 Hz), 7.82 (1H, d, J = 2.7 Hz), 12.96
Acknowledgements
1
3
(
1
1H, s). C NMR (DMSO-d ) δ : 111.0, 118.4, 121.7,
6
C
We gratefully acknowledge the support of this work by
the Shiraz University Research Council. We are also grateful
to Mr. H. Sajedian Fard and Mr. M.S. Darvish Tafvizi for
helpful cooperation.
22.6, 126.6, 128.2, 128.7, 133.6, 134.6, 147.0.
2
-(2-Pyridyl)-1H-benzimidazole (5n)
Purification by flash column chromatography, eluted with
n-hexane/ethyl acetate (7:1), gave compound 5n as a colour-
1
less powder in 85% yield. Mp 218 °C (Lit. 218 °C (29)). H
References
NMR (DMSO-d ) δ : 7.16–7.24 (2H, m), 7.47–7.71 (3H,
6
H
m), 7.98 (1H, dd, J = 7.7, J = 1.7 Hz), 8.30–8.34 (1H, m),
1
2
1
.
(a) M.J. Tebbe, W. A. Spitzer, F.Victor, S.C. Miller, C.C. Lee,
T.R.E. Mckinney, and C.J. Tang. J. Med. Chem. 40, 3937
1
3
8
.71 (1H, d, J = 6.9 Hz), 13.01 (1H, s). C NMR (DMSO-
d ) δ : 112.0, 119.2, 121.4, 121.9, 123.1, 124.6, 134.8,
1
6
C
(
1997); (b) K.L. Brown. Chem. Rev. 105, 2075 (2005).
37.5, 143.7, 148.4, 149.3, 150.7.
2
.
(a) A.R. Porcari, R.V. Devivar, L.S. Kucera, J.C. Drach, and
L.B. Townsend. J. Med. Chem. 41, 1252 (1998); (b) M. Roth,
M.L. Morningstar, P.L. Boyer, S.H. Hughes, R.W. Bukheit,
and C.J. Michejda. J. Med. Chem. 40, 4199 (1997).
2
-(2-Naphthyl)-1H-1,3-benzimidazole (5o)
Purification by flash column chromatography, eluted with
3
4
.
.
M.T. Migawa, J.L. Giradet, J.A. Walke, G.W. Koszalka, S.D.
Chamberlain, J.C. Drach, and L.B. Townsend. J. Med. Chem.
n-hexane/ethyl acetate (7:1), gave compound 5o as a colour-
1
less powder in 90% yield. Mp 217 °C (Lit. 219 °C (37)). H
4
1, 1242 (1998).
NMR (DMSO-d ) δ : 7.19 (2H, dd, J = 6.0, J = 3.0 Hz),
6
H
1
2
I. Tamm and P.B. Seghal. Adv. Virus Res. 22, 187 (1978).
7
8
1
1
.37–7.40 (2H, m), 7.59–7.77 (5H, m), 8.11 (1H, dd, J =
1
1
3
5. I. Tamm. Science (Washington, DC), 126, 1235 (1957).
.6, J = 1.7 Hz), 8.49 (1H, s). C NMR (DMSO-d ) δ :
2
6
C
6
.
A.A. Spasov, I.N. Yozhitsa, L.I. Bugaeva, and V.A. Anisimova.
15.2, 123.2, 123.6, 126.5, 126.8, 127.2, 127.8, 128.5,
29.0, 134.2, 138.1, 145.9, 151.6.
Pharm. Chem. J. 33, 232 (1999).
7
.
For comprehensive reviews on the chemistry of
benzimidazoles, see: (a) J.B. Wright. Chem. Rev. 48, 397
(1951); (b) P.N. Preston. Chem. Rev. 74, 279 (1974).
2
-(9-Anthryl)-1H-benzimidazole (5p)
Purification by flash column chromatography, eluted with
8. K. Niknam and A. Fatehi-Raviz. J. Iran. Chem. Soc. 4, 438
n-hexane/ethyl acetate (7:1), gave compound 5p as a yellow
(2007); available from www.ics-ir.org/jics.
1
9
.
(a) R.R. Nagawade and D.B. Shinde. Indian. J. Chem. B, 46,
49 (2007); (b) K. Bahrami, M.M. Khodaei, and F. Naali. J.
Org. Chem. 73 (2008). In press.
0. R.R. Nagawade and D.B. Shinde. Russ. J. Org. Chem. 42, 453
2006).
1. R. Trivedi, S.K. De, and R.A. Gibbs. J. Mol. Catal A: Chem.
45, 8 (2006).
powder in 90% yield. Mp 301 °C (Lit. 302–303 °C (38)). H
3
NMR (DMSO-d ) δ : 7.29 (2H, m), 7.46–7.72 (9H, m), 8.19
6
H
1
3
(
1
1
2H, d, J = 8.1 Hz), 8.83 (1H, s). C NMR (DMSO-d ) δ :
6 C
15.6, 122.6, 125.9, 126.1, 127.3, 127.6, 128.9, 129.3,
31.1, 134.2, 139.4, 146.7, 150.0.
1
1
1
(
2
2
-Phenyl-1H-benzimidazole-6-carboxylic acid (5q)
Purification by flash column chromatography, eluted with
2. T. Itoh, K. Nagata, H. Ishikawa, and A. Ohsawa. Heterocycles,
63, 2769 (2004).
n-hexane/ethyl acetate (7:1), gave compound 5q as a colour-
less powder in 80% yield. Mp 325 °C (Lit. 325 °C (20)). H
13. M. Curini, F. Epifano, F. Montanari, O. Rosati, and S.
1
Taccone. Synlett, 1832 (2004).
NMR (DMSO-d ) δ : 7.47–7.66 (4H, m), 7.84 (1H, d, J =
14. P. Sun and Z. Hu. J. Heterocyclic Chem. 43, 773 (2006).
15. R.R. Nagawade and D.B. Shinde. Chinese Chem. Lett. 17, 453
(2006).
6
H
1
3
8
.4 Hz), 8.17–8.20 (3H, m), 12.79 (1H, s), 13.19 (1H, s). C
NMR (DMSO-d ) δ : 122.7, 123.5, 124.0, 125.0, 126.7,
6
C
1
6. (a) M. Chakrabarty, S. Karmakar, A. Mukherji, S. Arima, and
Y. Harigaya. Heterocycles, 68, 967 (2006); (b) H. Sharghi, O.
Asemani, and M.H. Tabaei. J. Heterocycl. Chem. 45, 1 (2008).
7. U. Srinivas, Ch. Srinivas, P. Narender, V. Jayathirtha Rao, and
S. Palaniappan. Catal. Commun. 8, 107 (2007).
8. H. Sharghi, O. Asemani, and R. Khalifeh. Synth. Commun. 38,
1128 (2008).
9. J.G. Smith and I. Ho. Tetrahedron Lett. 12, 3541 (1971).
1
28.3, 129.2, 129.6, 130.3, 142.4, 153.7, 168.0.
5
-Methyl-2-phenyl-1H-benzimidazole (5r)
1
1
1
Recrystallization from EtOH/H O (2:1) gave compound
2
5
(
r as a colourless powder in 87% yield. Mp 242–243 °C
1
Lit. 242–143 °C (30)). H NMR (DMSO-d ) δ : 2.35 (3H,
6
H
S), 7.00 (1H, d, J = 8.1 Hz), 7.36–7.55 (5H, m), 8.14(2H, d,
J = 7.6 Hz), 12.75 (1H, s). 13C NMR (DMSO-d ) δ : 21.3,
6
C
20. (a) H. Sharghi, M.H. Beyzavi, and M.M. Doroodmand. Eur. J.
Org. Chem, 4126 (2008); (b) H. Sharghi, M. Aberi, and M.M.
Doroodmand. Advan. Synth. Catal. In press.
1
1
11.1, 118.4, 123.5, 126.2, 128.8, 129.2, 129.6, 130.3,
31.1, 150.9.
©
2008 NRC Canada