1404
H. Veisi, R. Gholbedaghi, J. Malakootikhah, A. Sedrpoushan, B. Maleki, and D. Kordestani
Vol 47
6.93 (m, 12H); 13C NMR (90 MHz, DMSO-d6): dc (ppm)
200.8, 160.5, 137.4, 136.8, 125.5, 124.4, 123.9, 121.0, 120.5,
118.3, 117.7, 117.0, 113.9, 111.7, 111.5; MS: m/z 364.
[9] Firouzabadi, H.; Iranpoor, N.; Jafari, A. A. J Mol Catal A
Chem 2005, 244, 168.
[10] Deb, M. L.; Bhuyan, P. J. Tetrahedron Lett 2006, 47, 1441.
[11] Zhang, Z.-H.; Yin, L.; Wang, Y.-M. Synthesis 2005, 1949.
[12] Li, J.-T.; Dai, H.-G.; Xu, W.-Z.; Li, T.-S. Ultrasonics Sono-
chem 2006, 13, 24.
Analytical data for compound (6). Pink solid, m.p.ꢀ: 1194–
195ꢁC; FTIR (KBr): 3405, 3049, 1622, 1455, 1216 cm
;
1H
NMR (90 MHz, DMSO-d6): dH (ppm) 5.75 (s, CH, 1H), 6.29
(s, 4H), 7.05–7.40 (m, CH aromatic, 20H), 7.31 (br s, NH,
4H); 13C NMR (90 MHz, DMSO-d6): dc (ppm) 142.5, 136.7,
128.1, 126.8, 123.6, 120.9, 119.2, 118.4, 118.3, 111.5, 29.1;
MS: m/z 566.200.
Analytical data for compound (8). Light red solid, m.p.:
208–210ꢁC; IR (KBr): 3421, 2950, 2900, 1635, 1506, 1457,
1377, 1216, 1173, 1082, 742 cmꢀ1 1H NMR (300 MHz,
;
[13] Bandgar, B. P.; Shaikh, K. A. Tetrahedron Lett 2003, 44,
1959.
[14] Karthik, M.; Tripathi, A. K.; Gupta, N. M.; Palanichamy,
M.; Murugesan, V. Catal Commun 2004, 5, 371.
´ ´
[15] Penieres-Carrillo, G.; Garcıa-Estrada, J. G.; Gutierrez-
´
Ramırez, J. L.; Alvarez-Toledano, C. Green Chem 2003, 5, 337.
[16] Ji, S.-J.; Zhou, M.-F.; Gu, D.-G.; Wang, S.-Y.; Loh, T.-P.
Synlett 2003, 2077.
DMSO-d6): dH (ppm) 5.01 (s, CH2 benzylic, 6H), 5.72 (s, CH,
3H), 6.74–7.50 (m, CH aromatic, 46H), 10.71 (s, NH, 6H);
13C NMR (300 MHz, DMSO-d6): dc (ppm) 40.08, 69.48,
111.85, 114.67, 115.24, 118.54, 118.82, 119.58, 121.25,
123.87, 127.05, 129.66, 137.03, 137.73, 138.15, 156.91; Anal.
Calcd. for C78H60N6O3: C, 82.95; H, 5.35; N, 7.44. Found: C,
82.52; H, 5.21; N, 7.36.
[17] Mo, L.-P.; Ma, Z.-C.; Zhang, Z.-H. Synth Commun 2005,
35, 1997.
[18] Mi, X.; Luo, S.; He, J.; Cheng, J.-P. Tetrahedron Lett 2004,
45, 4567.
[19] Kamble, V. T.; Kadam, K. R.; Joshi, N. S.; Muley, D. B.
Catal Commun 2007, 8, 498.
[20] Pradhan, P. K.; Dey, S.; Giri, V. S.; Jaisankar, P. Synthesis
2005, 1779.
Analytical data for compound (10). Red solid, m.p.: 250–
251ꢁC d; IR (KBr): 3417, 2926, 2854, 1609, 1506, 1456,
[21] Xia, M.; Wang, S. H.; Yuan, W. B. Synth Commun 2004,
34, 3175.
1
1413, 1338, 1218, 1172, 1127, 1012, 743 cmꢀ1; H NMR (300
[22] Ramesh, C.; Banerjee, J.; Pal, R.; Das, B. Adv Synth Catal
2003, 345, 557.
MHz, DMSO-d6): dH (ppm) 5.08 (s, CH2 benzylic, 8H), 5.76
(s, CH, 4H), 6.82–7.65 (m, CH aromatic, 60H), 10.70 (s, NH,
8H); 13C NMR (300 MHz, DMSO-d6): dc (ppm) 41.05, 70.40,
111.45, 114.52, 115.12, 117.85, 118.85, 119.26, 120.85,
122.82, 126.65, 129.26, 136.76, 137.43, 138.63, 157.43; Anal.
Calcd. for C102H78N8O4: C, 82.79; H, 5.31; N, 7.57. Found: C,
82.120; H, 5.20; N, 7.35.
[23] Reddy, B. M.; Sreekanth, P. M.; Lakshmanan, P. J Mol
Catal A Chem 2005, 237, 93.
[24] Firouzabadi, H.; Iranpoor, N.; Jafarpour, M.; Ghaderi, A.
J Mol Catal A Chem 2006, 253, 249.
[25] (a) Pore, D. M.; Desai, U. V.; Thopate, T. S.; Wadgaonkar, P. P.
Arkivoc 2006, 12, 75; (b) Zolfigol, M. A.; Salehi, P.; Shiri, M.; Sayadi, A.;
Abdoli, A.; Keypour, H.; Rezaeivala, M.; Niknam, K.; Kolvari, E. Mol
Divers 2008, 12, 203.
1
2,2 -Bisindolyl-phenylmethane (11). H NMR (90 MHz,
DMSO-d6): dH (ppm) 7.94 (br s, 2H), 7.22–7.66 (m, 13H),
6.04 (s, 1H), 2.23 (s, 6H); Anal. Calcd. for C25H22N2: C,
85.68; H, 6.33; N, 7.99. Found: C, 85.43; H, 5.95; N, 7.68;
MS: m/z 350.
[26] Hosseini-Sarvari, M. Acta Chim Slovenica 2007, 54, 354.
[27] Dabiri, M.; Salehi, P.; Baghbanzadeh, M.; Vakilzadeh, Y.;
Kiani, S. Monatshefte for Chemie 2007, 138, 595.
[28] Hagiwara, H.; Sekifuji, M.; Hoshi, T.; Qiao, K.; Yokoyama,
C. Synlett 2007, 1320.
Acknowledgments. The authors are thankful to Payame Noor
University (PNU), and the University of Sheffield for NMR,
Mass spectra and CHN. Also the author acknowledges Prof.
Turan Ozturk from the University of Istanbul Technical for his
useful comments and his kindness for hosting the author as a
research visitor.
[29] Kamble, V. T.; Bandgar, B. P.; Bavikar, S. N. Chin J Chem
2007, 25, 13.
[30] Niknam, K.; Zolfigol, M. A.; Sadabadi, T.; Nejati, A. J Iran
Chem Soc 2006, 3, 318.
[31] Lin, X. F.; Cui, S. L.; Wang, Y. G. Synth Commun 2006,
36, 3153.
[32] Zeng, X. F.; Ji, S. J. Lett Org Chem 2006, 3, 374.
[33] Zhang, L. P.; Li, Y. Q.; Zhou, M. Y. Chin Chem Lett 2006,
17, 723.
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet