Hasaninejad et al.
419
1
1
(
(
7
8
92%); mp 161–163 °C (lit. 163–165 °C) (6j). H NMR
2981, 1515. H NMR (CDCl , ppm) δ: 1.55 (d, 2H, J =
3
CDCl , ppm) δ: 5.96 (s, 1H, ArCH), 6.67 (s, 2H), 7.08–
.15 (m, 4H), 7.36 (d, 2H, J = 8.1 Hz), 7.43 (d, 2H, J =
.1 Hz), 7.37 (d, 2H, J = 7.9 Hz), 7.99 (br, 2H, NH), 8.34
4.1 Hz), 1.73 (d, 4H, J = 4.0 Hz), 2.11 (s, 6H), 2.52–2.56
(m, 4H), 6.71–6.96 (m, 6H), 7.22 (d, 2H, J = 7.9 Hz), 7.98
(br, 2H, NH).
3
(
d, 2H, J = 7.9 Hz).
Acknowledgements
3
-(Furan-2-yl(1H-indol-3-yl)methyl)-1H-indole (9)
Recrystallization from EtOAc – petroleum ether (1:1)
We gratefully acknowledge the support of this work by
Persian Gulf University Research Councils.
gave brown solid; yield: 0.282 g (90%); mp > 300 °C (lit.
>
–
1
1
300 °C) (12). IR (KBr, cm ): 3410, 1712, 1450. H NMR
(
7
CDCl , ppm) δ: 5.97 (s, 1H, ArCH), 6.90 (s, 2H), 7.08–
3
References
.43 (m, 11H), 8.00 (br, 2H, NH).
1
. K.W Lo, K.H.K. Tsang, W.K. Hui, and N. Zhu. Chem.
Commun. 2704 (2003).
3
-(1-(1H-Indol-3-yl)pentyl)-1H-indole (10)
Purification by plate chromatography, eluted with EtOAc –
2
. J.R. Plimmer, D.W. Gammon, and N.N. Ragsdale. Encyclope-
dia of agrochemicals. Vol. 3. John Wiley and Sons, New York.
2003.
petroleum ether (1:2), gave colorless solid; yield: 0.256 g
(
1
1
6
7
–
1
85%); mp 80–82 °C (6l). IR (KBr, cm ): 3448, 3070, 2962,
1
3. A. Ramirez and S. Garcia-Rubio. Curr. Med. Chem. 1891
2003).
510. H NMR (CDCl , ppm) δ: 0.91 (t, 3H, J = 6.8 Hz),
3
(
.29 (m, 2H), 1.61 (m, 2H), 2.30 (m, 2H), 4.75 (t, 1H, J =
.7 Hz), 6.89 (s, 2H), 7.05–7.13 (m, 4H), 7.28 (d, 2H, J =
.9 Hz), 7.52 (d, 2H, J = 7.9 Hz), 7.91 (br, 2H, NH).
4
5
6
. S. Zhao, X. Liao, and J.M. Cook. Org. Lett. 687 (2002), and
refs. cited therein.
. B. Jiang, C.G. Yang, and J. Wang. J. Org. Chem. 67, 1396
(
2002).
. (a) A. Kamal and A.A. Qureshi. Tetrahedron, 19, 513 (1963);
b) G. Babu, N. Sridhar, and P.T. Perumal. Synth. Commun.
0, 1609 (2000); (c) R. Nagarajan and P.T. Perumal. Tetrahe-
3
-(1-(1H-Indol-3-yl)-1-phenylethyl)-1H-indole (11)
Purification by plate chromatography, eluted with EtOAc –
(
3
petroleum ether (1:1), gave colorless solid; yield: 0.236 g
–1
(70%); mp 164–166 °C (lit. 165–167 °C) (11). IR (KBr, cm ):
dron, 58, 1229 (2002); (d) B.P. Bandgar and K.A. Shaikh. J.
Chem. Res. Synop. 34 (2004); (e) X.L. Mi, S.Z. Luo, J.Q. He,
and J.P. Cheng. Tetrahedron Lett. 45, 4567 (2004); (f) D.
Chen, L. Yu, and P.G. Wang. Tetrahedron Lett. 37, 4467
1
3
3
400, 3065, 2973, 1595. H NMR (CDCl , ppm) δ: 2.41 (s,
3
H, CH ), 6.65 (s, 2H), 6.95 (t, 2H, J = 7.5 Hz), 7.16 (t, 2H,
3
J = 7.5 Hz), 7.27–7.44 (m, 9H), 7.92 (br, 2H, NH).
(
1996); (g) M. Xia, S.B. Wang, and W.B. Yuan. Synth.
3
-(1-(1H-Indol-3-yl)cyclohexyl)-1H-indole (12)
Commun. 34, 3175 (2004); (h) H. Koshima and W. Matsuaka.
J. Heterocycl. Chem. 39, 1089 (2002); (i) R. Nagarajan and
P.T. Perumal. Synth. Commun. 32, 105 (2002); (j) G.V.M.
Sharma, J.J. Reddy, P.S. Lakshmi, and P.R. Krishna. Tetrahe-
dron Lett. 45, 7729 (2004); (k) H. Firouzabadi, N. Iranpoor,
and A.A. Jafari. J. Mol. Catal. A: Chem. 244, 168 (2006);
(l) H. Firouzabadi, N. Iranpoor, M. Jafarpour, and A. Ghaderi.
J. Mol. Cat. A: Chem. 253, 249 (2006); (m) K. Tabatabaeian,
M. Mamaghani, N. Mahmoodi, and A. Khorshidi. Can. J.
Chem. 84, 1541(2006); (n) M.L. Deb and P.J. Bhuyan. Tetra-
hedron Lett. 47, 1441 (2006).
Purification by plate chromatography, eluted with chloro-
form – petroleum ether (1:1), gave colorless solid; yield:
–
1
0
3
1
.247 g (75%); mp 163–165 °C (11). IR (KBr, cm ): 3442,
1
055, 2972, 1512. H NMR (CDCl , ppm) δ: 1.61 (m, 2H),
3
.69 (m, 4H), 2.54–2.57 (m, 4H), 6.91 (s, 2H), 7.05–7.12
(
m, 4H), 7.34 (d, 2H, J = 7.8 Hz), 7.58 (d, 2H, J = 7.5 Hz),
7
.94 (br, 2H, NH).
2
-Methyl-3-((2-methyl-1H-indol-3-yl)(phenyl)methyl)-1H-
indole (13)
7
. (a) D. Habibi, N. Mahmoodi, and O. Marvi. Can. J. Chem. 85,
1
Purification by plate chromatography, eluted with chloro-
form – petroleum ether (1/2), gave pink solid; yield: 0.319 g
(2007); (b) K.A. Stephenson, S.R. Banerjee, N. McFarlane,
–
1
D.R. Boreham, K.P. Maresca, J.W. Babich, J. Zubieta, and J.F.
Valliant. Can. J. Chem. 83, 2060 (2005); (c) K. Tanaka.
Solvent-free organic synthesis. Wiley-VCH, GmbH and
KGaA, Weinheim. 2004; (d) A. Loupy. Microwave in Organic
synthesis. Wiley-VCH, Weinheim. 2004; (e) A. Zare, A.
Hasaninejad, A. Khalafi-Nezhad, A.R. Moosavi Zare, A.
Parhami, and G.R. Nejabat. Arkivoc, i, 58 (2007); (f) A.
Khalafi-Nezhad, A. Zare, A. Parhami, M.N. Soltani Rad, and
G.R. Nejabat. Phosphorus, Sulfur Silicon Relat. Elem. 182,
(
91%); mp 245–247 °C (6l). IR (KBr, cm ): 3405, 3064,
1
1
1
7
595, 1512. H NMR (CDCl , ppm) δ: 2.05 (s, 6H), 5.88 (s,
3
H, ArCH), 6.78–7.01 (m, 6H), 7.14–7.22 (m, 5H), 7.28–
.31 (m, 2H), 8.02 (br, 2H, NH).
2
1
-Methyl-3-((2-methyl-1H-indol-3-yl)(4-nitrophenyl)methyl)-
H-indole (14)
Recrystallization from EtOAc – petroleum ether (1:1)
gave yellow solid; yield: 0.364 g (92%); mp 241–243 °C
6
57 (2007); (g) A. Hasaninejad and A. Zare. J. Sulfur Chem.
–
1
1
(
(
6
6l); IR (KBr, cm ): 3398, 3051, 1590, 1515. H NMR
CDCl , ppm) δ: 2.13 (s, 6H), 5.96 (s, 1H), 6.71–6.96 (m,
In press; (h) A. Khalafi-Nezhad, A. Zare, A. Parhami, M.N.
Soltani Rad, and G.R. Nejabat. Synth. Commun. 36, 3549
(
3
H), 7.21 (d, 2H, J = 8.0 Hz), 7.47 (d, 2H, J = 8.5 Hz), 8.03
2006); (i) A. Khalafi-Nezhad, A. Zare, M.N. Soltani Rad, B.
(
d, 2H, J = 8.5 Hz), 8.04 (br, 2H, NH).
Mokhtari, and A. Parhami. Synthesis, 419 (2005).
8
. (a) M. Chakrabarti and S. Sarkar. Tetrahedron Lett. 43, 1351
2
-Methyl-3-(1-(2-methyl-1H-indol-3-yl)cyclohexyl)-1H-
(
2002); (b) M. Chakrabarti, N. Gosh, R. Basak, and Y.
indole (15)
Harigaya. Tetrahedron Lett. 43, 4075 (2002).
Purification by plate chromatography, eluted with chloro-
form – petroleum ether (1:1) gave colorless solid; yield:
9. (a) H. Sharghi and A.R. Hassani Nejad. J.Chem. Res. Synop.
87 (2003); (b) A. Hasaninejad and H. Sharghi. Phosphorus,
Sulfur Silicon Relat. Elem. 182, 873 (2007).
–
1
0
.262 g (73%); mp 81–84 (6l). IR (KBr, cm ): 3450, 3043,
©
2007 NRC Canada