Silica Supported Sodium Hydrogen Sulfate and Amberlyst-15
COMMUNICATIONS
Stirring was continued. After completion of the reaction as
indicated by TLC, the catalyst was filtered off and washed with
EtOAc )2 Â 5 mL). The filtrate and washings were combined
and the solvents were removed under vacuum. The residue was
purified by column chromatography over silica gel using
mixtures of hexane and EtOAc as eluent to afford the bis- and
tris)1H-indol-3-yl)methanes.
References and Notes
[1] Part 25 in the series, ªStudies on Novel Synthetic
Methodologiesº, for part 24, see N. Ravindranath, C.
Ramesh, R. Ramu, B. Das, Chem. Lett. 2003, )submitted).
[2] a) R. J. Sundberg, The Chemistry of Indoles, Academic
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Nat. Prod. Rep. 2000, 17, 175; c) S. Hibino, T. Chozi, Nat.
Prod. Rep. 2001, 18, 66.
[3] a) B. Gregorovich, K. Liang, D. Chegston, S. MacDonald,
Can. J. Chem. 1968, 46, 3291; b) M. Roomi, S. MacDonald,
Can. J. Chem. 1970, 48, 139.
[4] a) W. E. Noland, M. R. Venkiteswaren, C. G. Richards, J.
Org. Chem. 1961, 26, 4241; b) A. Chatterjee, S. Manna, J.
Banerji, C. Pascard, T. Prange, J. N. Shoolery, J. Chem.
Soc. Perkin Trans. 1 1980, 553; c) J. Banerji, A. Chatterjee,
S. Manna, C. Pascard, T. Prange, J. N. Shoolery, Hetero-
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Spectroscopic Data of Representative Bis- and
Tris!1H-indol-3-yl)methanes
3 g: IR )KBr): n
3403, 1747, 1484, 1456 cmÀ1; 1H NMR
)CDCl3): d 7.86 )2H, br s), 7.44 ± 7.02 )12H, m), 6.62 )2H, d,
.
J
2.4 Hz), 5.98 )1H, s), 1.98 )3H, s); EIMS: m/z 380 )M ),
338, 221, 156, 142.
3 m: IR )KBr): n 3403, 1599, 1509, 1458 cm ; H NMR
À1
1
)CDCl3): d 7.56 )4H, m), 7.24 ± 7.02 )8H, m), 6.78 )2H, d, J
8.0 Hz), 5.88 )1H, s), 4.64 )1H, br s), 2.17 )6H, s); EIMS: m/z
.
366 )M ), 351, 257, 235, 220, 183.
À1
1
3p: IR )KBr): n 3416, 1612, 1456 cm ; H NMR )CDCl3):
d 7.62 )2H, br s), 7.24 )2H, d, J 8.0 Hz), 7.35 ± 6.83 )11H, m),
6.78 )2H, d, J 2.4 Hz), 4.42 )1H, t, J 7.0 Hz), 2.76 ± 2.58 )2H,
.
m), 2.46 )2H, t, J 7.0 Hz); EIMS: m/z 350 )M ), 245, 232,
155, 141.
À1
1
3 s: IR )KBr): n 3430, 3400, 1620, 1470 cm ; H NMR
)CDCl3 DMSO-d6): d 9.89 )3H, br s), 7.39 )3H, d, J
[5] R. Fricke, H. Hosslick, G. Lischke, M. Richter, Chem. Rev.
2000, 100, 2303.
8.0 Hz), 7.24 )3H, d, J 8.0 Hz), 6.98 )3H, t, J 8.0 Hz), 6.82
)3H, t, J 8.0 Hz), 6.69 )3H, d, J 2.4 Hz), 6.40 )1H, s); EIMS:
m/z 361)M ), 243, 216, 117.
[6] a) A. K. Maiti, P. Bhattacharyya, J. Chem. Res. Synop.
1997, 424; b) J. Banerji, U. Dutta, B. Basak, M. Saha, H.
Budzikiewicz, A. Chatterjee, Indian J. Chem. 2001, 40B,
981; c) M. Chakrabarty, S. Sarkar, Tetrahedron Lett. 2002,
43, 1351.
.
Acknowledgements
[7] L. Yu, D. Chen, J. Li, P. G. Wang, J. Org. Chem. 1997, 62,
3575.
[8] J. S. Yadav, B. V. S. Reddy, S. Sunitha, Adv. Synth. Catal.
2003, 345, 349.
The authors thank UGC and CSIR New Delhi for financial
assistance.
[9] H. Firouzabadi, N. Iranpoor, B. Karimi, H. Hazarkhani,
Synlett 2000, 263.
Adv. Synth. Catal. 2003, 345, 557 ± 559
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