6938
T.K. Chaitanya et al. / Tetrahedron 67 (2011) 6934e6938
4, 149; (d) Stiborova, M.; Rupertova, M. S.; Dohalska, M. B.; Weissler, M.; Frei, E.
2-phenylethynylcarbazole (1aeg), 1,2-aryldiamine (0.5 mmol)
(2ae2f) and 5 mL of dimethylformamide. The reaction mixture was
heated at 120 ꢀC for 2 h under stirring until complete consumption
of starting material as monitored by TLC. After the reaction was
completed, the reaction mixture was extracted with ethyl acetate,
dried over anhydrous sodium sulfate, and evaporated in vacuum.
The residue was adsorbed on silica gel and purified by column
chromatography using silica gel (94:6 hexane/ethyl acetate) to af-
ford the desired product.
€
Chem. Res. Toxicol. 2003, 16, 38; (e) Knolker, H.-J.; Reddy, K. R. Chem. Rev. 2002,
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2.2.1. Compound (6). Mp: 198e200 ꢀC; IR (KBr): 1635, 1610, 1529,
1467, 1302, 1230, 734, 700 cmꢁ1; hexane/EtOAc (4:1); Rf¼0.40; 1H
ꢁ
halingam, A. K.; Wu, X.; Johansson, B.; Holm, M.; Botoros, M.; Karlen, A.; Pet-
€
tersson, A.; Nyberg, F.; Fandriks, L.; Gallo-Payet, N.; Hallberg, A.; Alterman, M. J.
NMR (400 MHz, CDCl3, TMS) d 9.62 (1H, s), 8.12 (1H, s), 8.04 (1H, s),
Med. Chem. 2004, 47, 5995; (d) Vega, J. A.; Vaquero, J. J.; Alvarez-Builla, J.;
Ezquerra, J.; Hamdouchi, C. Tetrahedron 1999, 55, 2317; (e) Venable, J. D.; Cai,
H.; Chai, W.; Dvorak, C. A.; Grice, C. A.; Jablonowski, J. A.; Shah, C. R.; Kwok, A.
K.; Ly, K. S.; Pio, B.; Wei, J.; Desai, P. J.; Jiang, W.; Nguyen, S.; Ling, P.; Wilson, S.
J.; Dunford, P. J.; Thurmond, R. L.; Lovenberg, T. W.; Karlsson, L.; Carruthers, N.
I.; Edwards, J. P. J. Med. Chem. 2005, 48, 8289.
7.34e7.64 (5H, s), 7.32e7.34 (4H, m), 6.52 (2H, s), 6.50 (1H, s), 4.41
(2H, s), 2.62 (3H, s), 1.48 (3H, s); 13C NMR (100 MHz, CDCl3, TMS)
d:
149.7, 144.3, 141.9, 139.9, 136.3, 135.0, 131.0, 130.0, 129.7, 129.5,
129.2, 129.0, 128.3, 124.6, 123.8, 123.1, 121.4, 120.6, 119.1, 117.4, 115.2,
113.8, 113.4, 108.3, 103.8 (aromatic C), 37.8, 21.5, 13.6 (aliphatic C);
m/z¼426, positive mode; Anal. Calcd for C30H23N3: C, 84.68; H,
5.45; N, 9.87%; found: C, 84.51; H, 5.41; N, 9.93%.
ꢁ
ꢁ
~
5. (a) Hranjec, M.; Pavlovic, G.; Marjanovic, M.; Kralj, M.; Karminski-Zamola, G.
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M. D. Chem.dEur. J. 2010, 16, 12052; (j) Bian, M.; Yao, W.; Ding, H.; Ma, C. J.
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A. P. J. Org. Chem. 2010, 75, 7691.
2.2.2. Compound (7). Mp: 197e199 ꢀC; IR (KBr): 1628, 1610, 1529,
1467, 1230, 1014, 869, 792, 734, 700, 576 cmꢁ1; hexane/EtOAc (4:1);
Rf¼0.43; 1H NMR (400 MHz, CDCl3, TMS)
d 9.61 (1H, s), 8.25 (1H, d,
J¼8.0 Hz), 8.19 (1H, d, J¼3.6 Hz), 8.14 (1H, s), 7.74 (2H, d, J¼6.0 Hz),
7.56e7.62 (4H, m), 7.35e7.41 (3H, m), 7.12 (1H, s), 4.60 (2H, q,
J¼8.0 Hz), 2.61 (3H, s), 1.51 (3H, s); 13C NMR (100 MHz, CDCl3, TMS)
d
150.3, 145.0, 142.3, 141.5, 140.0, 136.4, 136.3, 134.7, 130.6, 129.7,
129.4, 129.0, 128.5, 127.7, 126.0, 124.8, 123.0, 121.5, 119.7, 117.2, 115.2,
114.9, 108.4, 104.1 (aromatic C), 37.9, 21.5, 13.6 (aliphatic C); m/
z¼427, positive mode; Anal. Calcd for C29H22N4: C, 81.66; H, 5.20; N,
13.14%; found: C, 81.52; H, 5.23; N, 13.07%.
Acknowledgements
This work is supported by DST, India (Proj. No. SR/S1/OC-70/
2008) and T.K.C. thanks CSIR for providing SRF and K.S.P. thanks
UGC for JRF; Bharat, Anand and Prabhu for their timely help in
solving X-ray structure analyses.
9. (a) Sreenivas, D. K.; Nagarajan, R. Tetrahedron 2010, 66, 9650; (b) Gaddam, V.;
Ramesh, S.; Nagarajan, R. Tetrahedron 2010, 66, 4218.
10. Chaitanya, T. K.; Nagarajan, R. Org. Biomol. Chem. 2011, 9, 4662.
11. (a) Kale, R. P.; Shaikh, M. U.; Jadhav, G. R.; Gill, C. H. Tetrahedron Lett. 2009, 50,
1780; (b) Sindi, K.; Kahn, P. H.; Kaddachi, M. T. Phys. Chem. News 2007, 35, 113;
(c) Lin, S.-Y.; Isome, Y.; Stewart, E.; Liu, J.-F.; Yohannes, D.; Yu, L. Tetrahedron Lett.
2006, 47, 2883; (d) Dubey, P. K.; Kumar, R. V.; Kulkarni, S. M.; Sunder, G. H.;
Smith, G.; Kennard, C. H. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.
2004, 43B, 952; (e) Vanden, E.; Jean, J.; Mayence, A.; Maquestiau, A.; Anders, E.
Bull. Soc. Chim. Belg. 1993, 102, 357.
12. (a) The CCDC deposition number of 7 is 814066; Molecular formula: C29H22N4,
unit cell parameters: a 9.3186(15) b 18.272(2) c 13.1361(18) beta 99.788(12)
space group P21/n. (b) The CCDC deposition number of 8 is 814065; molecular
formula: C34H27N3O1, unit cell parameters: a 18.3228(9) c 26.723(3) gamma
120.00 space group P-3c1.
Supplementary data
Supplementary data associated with this article can be found, in
References and notes
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