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A. Khalafi-Nezhad et al.
PAPER
(CaCl2) and evaporated. The crude product was subjected to column
chromatography (silica gel, EtOAc–n-hexane, 1:4) to obtain the
pure product.
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3-[(1H-Indol-3-yl)(phenyl)methyl]-1H-indole (3a)
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IR (KBr): 3402, 3051, 1618, 1600 cm–1.
1H NMR (CDCl3): d = 5.86 (s, 1 H, ArCH), 6.66 (s, 2 H), 7.11 (t,
J = 6.9 Hz, 2 H), 7.14–7.22 (m, 3 H), 7.28–7.31 (m, 2 H), 7.35–7.42
(m, 6 H), 7.93 (br, 2 H, NH).
13C NMR (CDCl3): d = 31.6, 110.9, 111.9, 118.4, 119.5, 121.2,
124.0, 126.3, 127.1, 128.5, 128.6, 137.0, 145.2.
MS: m/z = 322 (M+).
Anal. Calcd for C23H18N2: C, 85.68; H, 5.63; N, 8.69. Found: C,
85.55; H, 5.76; N, 8.84.
3-[(2-Furyl(1H-indol-3-yl)methyl]-1H-indole (3k)
IR (KBr): 3410, 1712, 1450 cm–1.
1H NMR (CDCl3): d = 5.97 (s, 1 H, ArCH), 6.90 (s, 2 H), 7.08–7.43
(m, 11 H), 8.00 (br, 2 H, NH).
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Silicon Relat. Elem. 2004, 179, 2273.
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5, 424.
13C NMR (CDCl3): d = 34.8, 106.5, 110.2, 111.3, 112.2, 118.0,
119.3, 119.7, 121.7, 124.3, 126.3, 135.9, 142.0.
MS: m/z = 312 (M+).
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1351.
Anal. Calcd for C21H16N2O: C, 80.75; H, 5.16; N, 8.97. Found: C,
80.86; H, 5.29; N, 8.81.
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Acknowledgment
We acknowledge Shiraz University for partial support of this work
and thank Mr. H. Sajedianfard and Mr. M. S. Darvish Tafvizi for
running NMR and MS determinations, respectively.
(31) (a) Khalafi-Nezhad, A.; Hashemi, A. J. Chem. Res. 1999, 12,
720. (b) Khalafi-Nezhad, A.; Fareghi Alamdari, R.; Zekri,
N. Tetrahedron 2000, 56, 7503. (c) Khalafi-Nezhad, A.;
Hashemi, A. Iran. J. Chem. Chem. Eng. 2001, 20, 9.
(d) Khalafi-Nezhad, A.; Soltani Rad, M. N.; Hakimelahi, G.
H. Helv. Chim. Acta 2003, 86, 2396. (e) Khalafi-Nezha, A.;
Mokhtari, B.; Soltani Rad, M. N. Tetrahedron Lett. 2003, 40,
7325. (f) Khalafi-Nezhad, A.; Soltani Rad, M. N.;
Khoshnood, A. Synthesis 2004, 583. (g) Khalafi-Nezhad,
A.; Mokhtari, B. Tetrahedron Lett. 2004, 45, 6737.
(h) Khalafi-Nezhad, A.; Zare, A.; Soltani Rad, M. N.;
Mokhtari, B.; Parhami, A. Synthesis 2005, 419. (i) Khalafi-
Nezhad, A.; Parhami, A.; Soltani Rad, M. N.; Zare, A.
Tetrahedron Lett. 2005, 46, 6879. (j) Khalafi-Nezhad, A.;
Zare, A.; Parhami, A.; Soltani Rad, M. N.; Nejabat, G. R.
Can. J. Chem. 2006, 84, 979. (k) Khalafi-Nezhad, A.; Zare,
A.; Parhami, A.; Soltani Rad, M. N.; Nejabat, G. R. Synth.
Commun. 2006, 36, 3549. (l) Khalafi-Nezhad, A.; Zare, A.;
Parhami, A.; Soltani Rad, M. N.; Nejabat, G. R. Phosphorus,
Sulfur Silicon Relat. Elem. 2007, 182, 657. (m) Zare, A.;
Hassaninejad, A.; Mousavi Zare, A. R.; Parhami, A.;
Sharghi, H.; Khalafi-Nezhad, A. Can. J. Chem. 2007, 85,
438. (n) Zare, A.; Hassaninejad, A.; Khalafi-Nezhad, A.;
Mousavi Zare, A. R.; Parhami, A. ARKIVOK 2007, (xiii),
105. (o) Zare, A.; Hassaninejad, A.; Khalafi-Nezhad, A.;
Mousavi Zare, A. R.; Parhami, A. ARKIVOK 2007, (xiii),
58. (p) Imanzadeh, G. H.; Khalafi-Nezhad, A.; Mousavi
Zare, A. R.; Zare, A.; Parhami, A. J. Iran. Chem. Soc. 2007,
4, 229. (q) Khalafi-Nezhad, A.; Zare, A.; Parhami, A.;
Soltani Rad, M. N.; Nejabat, G. R. J. Iran. Chem. Soc. 2007,
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Synthesis 2008, No. 4, 617–621 © Thieme Stuttgart · New York