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RSC Advances
1.80–1.89 (m, 4H); 13C NMR (75 MHz, CDCl3): d 132.3, 130.1,
129.7, 128.9, 125.1, 123.3, 123.1, 121.5, 119.8 119.2, 118.5,
112.0, 23.4, 21.1; MS (EI, m/z): 221 [M]+; HRMS (ESI): Calcd. for
C16H16N [M+H]+: 222.12827; found: 222.12796.
Mixture of 2-methyl-1H-indole (4f) and 3-methyl-1H-indole
(4f9). The ratio of 4f and 4f9 was determined by GC and GC
analysis using hexadecane as an internal standard. 4f : 4f9 =
11 : 3.
3-Chloro-6,7,8,9-tetrahydro-5H-carbazole (3k). White solid,
mp 146–148 uC (lit.17d 146–147 uC); 1H NMR (300 MHz, CDCl3):
d 7.61 (br, 1H), 7.33 (d, J = 1.5 Hz, 1H), 7.09 (d, J = 8.4 Hz, 1H),
6.97 (dd, J = 1.5 Hz, 1H), 2.56–2.66 (m, 4H), 1.75–1.87 (m, 4H);
13C NMR (75 MHz, CDCl3): d 135.8, 134.0, 129.0, 124.8, 121.1,
117.4, 111.2, 110.2, 23.3, 23.2, 23.1, 20.8; MS (EI, m/z): 205
[M]+; HRMS (ESI): Calcd. for C12H12NCl [M+H]+: 205.06582;
found: 205.06533.
3,5-Dimethyl-2-phenyl-1H-indole (4g). White solid, mp 100–
1
102 uC (lit.17g 102–103 uC); H NMR (300 MHz, CDCl3): d 7.85
(br, 1H), 7.49–7.52 (m, 2H), 7.37–7.42 (s, 2H), 7.19–7.31 (m,
3H), 7.00 (dd, J = 8.1 Hz, 1H), 2.41 (s, 3H), 2.37 (s, 3H); 13C
NMR (75 MHz, CDCl3): d 134.2, 133.5, 130.3, 128.8, 128.7,
127.7, 127.2, 123.9, 118.7, 110.3, 108.3, 21.6, 9.7; MS (EI, m/z):
221 [M]+; HRMS (ESI): Calcd. for C16H15N [M+H]+: 221.12044;
found: 221.12012.
1-Methyl-1H-indole (3l). Yellow oil; yellow liquid; 7.71–7.74
(m, 1H), 7.41 (d, J = 8.4 Hz, 1H), 7.27–7.35 (m, 1H), 7.18–7.24
(m, 1H), 7.12 (d, J = 3.0 Hz, 1H), 6.57–6.59 (m, 1H), 3.84 (s, 3H);
13C NMR (75 MHz, CDCl3): d 136.8, 128.9, 128.5, 121.6, 120.9,
119.3, 109.3, 100.9, 32.8; MS (EI, m/z): 131 [M]+; HRMS (ESI):
Calcd. for C9H10N [M+H]+: 132.08132; found: 132.08056.
5-Methyl-2-phenyl-1H-indole (4a). White solid, mp 209–210
Acknowledgements
The authors are grateful to the funds of the National Natural
Science Foundation of China (21101080), Fundamental
Research Funds for the Central Universities of China
(JUSRP10905, JUSRP211A07 and 1045210372090460), Natural
Science Foundation of Jiangsu Province (BK2011144), and
‘‘333 Talent Project of Jiangsu Province’’.
1
uC (lit.17e 211–213 uC); H NMR (300 MHz, CDCl3): d 8.15 (br,
1H), 7.54–7.59 (m, 2H), 7.09–7.12 (m, 3H), 7.19–7.26 (m, 2H),
6.94 (dd, J = 1.2 Hz, 1H), 6.66–6.68 (m, 1H), 2.37 (s, 3H); 13C
NMR (75 MHz, CDCl3): d 138.0, 135.2, 132.6, 129.6, 129.5,
129.0, 127.6, 125.1, 124.0, 120.4, 110.6, 99.6, 21.5; MS (EI, m/z):
207 [M]+; HRMS (ESI): Calcd. for C15H14N [M+H]+: 208.11262;
found: 208.11173.
References
1 M. Butters, D. Catterick, A. Craig, A. Curzons, D. Dale,
A. Gillmore, S. P. Green, I. Marziano, J. P. Sherlock and
W. White, Chem. Rev., 2006, 106, 3002–3027.
5-Methoxy-2-phenyl-1H-indole (4b). White solid, mp 160–
1
162 uC (lit.17e 160–162 uC); H NMR (300 MHz, CDCl3): d 8.15
(br, 1H), 7.54–7.58 (m, 2H), 7.33–7.39 (m, 2H), 7.19–7.27 (m,
2H), 7.02 (d, J = 2.1 Hz, 1H), 6.78 (dd, J = 2.7 Hz, J = 2.4 Hz, 1H),
6.67–6.69 (m, 1H), 3.79 (s, 3H); 13C NMR (75 MHz, CDCl3): d
154.6, 138.7, 132.5, 132.1, 129.8, 129.1, 127.7, 125.1, 112.7,
111.7, 102.3, 99.9, 55.9; MS (EI, m/z): 223 [M]+; HRMS (ESI):
Calcd. for C15H14NO [M+H]+: 224.10753; found: 224.10723.
6-Methoxy-2-phenyl-1H-indole (4c). White solid, mp 172–174
2 (a) W. Gul and M. T. Hamann, Life Sci., 2005, 78, 442–453; (b)
A. Aygun and U. Pindur, Curr. Med. Chem., 2003, 10, 1113–1127;
(c) B. Suenkel, F. Fischer and C. Steegborn, Bioorg. Med. Chem.
Lett., 2013, 23, 143–146; (d) H. Johansson, T. B. Jorgensen, D.
E. Gloriam, H. Brauner-Osborne and D. S. Pedersen, RSC Adv.,
2013, 3, 945–960; (e) A. J. Kochanowska-Karamyan and M.
T. Hamann, Chem. Rev., 2010, 110, 4489–4497.
3 (a) B. Biersack and R. Schobert, Curr. Drug Targets, 2012,
13, 1705–1719; (b) K. Krueger, A. Tillack and M. Beller, Adv.
Synth. Catal., 2008, 350, 2153–2167.
4 (a) X. H. Zhang, Y. Cui, R. Katoh, N. Koumura and K. Hara,
J. Phys. Chem. C, 2010, 114, 18283–18290; (b) Q. Q. Li, L.
L. Lu, C. Zhong, J. Shi, Q. Huang, X. B. Jin, T. Y. Peng, J.
G. Qin and Z. Li, J. Phys. Chem. B, 2009, 113, 14588–14595;
(c) Y. Okada, T. Hihara and Z. Morita, Dyes Pigm., 2009, 83,
237–248.
5 (a) M. S. Park, D. H. Choi, B. S. Lee and J. Y. Lee, J. Mater. Chem.,
2012, 22, 3099–3104; (b) R. Paspirgelyte, R. Zostautiene, J.
V. Grazulevicius, S. Grigalevicius, C. C. Chen, Y. C. Chung, W.
B. Wang and J. H. Jou, Synth. Met., 2010, 160, 162–168; (c) Q. Q. Li,
Z. Li and J. G. Qin, Prog. Chem., 2009, 21, 2578–2588.
6 (a) E. Fischer and F. Jourdan, Ber. Dtsch. Chem. Ges., 1883,
16, 2241–2245; (b) W. Madelung, Ber. Dtsch. Chem. Ges.,
1912, 45, 1128; (c) A. Bischler, Ber. Dtsch. Chem. Ges., 1892,
25, 2860–2879; (d) C. D. Nenitzescu, Bull. Soc. Chim.
Romania., 1929, 11, 37; (e) R. C. Larock and E. K. Yum, J.
Am. Chem. Soc., 1991, 113, 6689–6690.
7 (a) M. Shiri, Chem. Rev., 2012, 112, 3508–3549; (b) J.
M. Knapp, J. S. Zhu, D. J. Tantillo and M. J. Kurth, Angew.
Chem., Int. Ed., 2012, 51, 10588–10591; (c) A. Porcheddu, M.
G. Mura, L. De Luca, M. Pizzetti and M. Taddei, Org. Lett.,
1
uC (lit.17e 173–176 uC); H NMR (300 MHz, CDCl3): d 8.16 (br,
1H), 7.52–7.56 (m, 2H), 7.32–7.44 (m, 3H), 7.18–7.24 (m, 1H),
6.82 (d, J = 2.4 Hz, 1H), 6.72 (dd, J = 2.4 Hz, J = 2.4 Hz, 1H),
6.67–6.69 (m, 1H), 3.79 (s, 3H); 13C NMR (75 MHz, CDCl3): d
156.8, 137.7, 136.9, 132.6, 129.0, 127.3, 124.8, 123.6, 121.3,
110.3, 99.9, 94.5, 55.7; MS (EI, m/z): 223 [M]+; HRMS (ESI):
Calcd. for C15H14NO [M+H]+: 224.10753; found: 224.10736.
2-Phenyl-1H-indole (4d). White solid, mp 188–190 uC (lit.17e
187–188 uC); 1H NMR (300 MHz, CDCl3): d 8.23 (br, 1H), 7.54–
7.59 (m, 3H), 7.21–7.39 (m, 4H), 7.01–7.16 (m, 2H), 6.75 (dd, J =
1.2 Hz, J = 1.2 Hz, 1H); 13C NMR (75 MHz, CDCl3): d 137.9,
136.9, 132.4, 129.3, 129.1, 127.8, 125.2, 122.4, 120.7, 120.3,
111.0, 100.0; MS (EI, m/z): 193 [M]+; HRMS (ESI): Calcd. for
C14H12N [M+H]+: 194.09697; found: 194.09624.
2-Phenyl-1H-benzo[g]indole (4e). White solid, mp 166–167
1
uC (lit.17f 165–167 uC); H NMR (300 MHz, CDCl3): d 9.00 (br,
1H), 7.96 (d, J = 8.1 Hz, 1H), 7.83 (d, J = 8.1 Hz, 1H), 7.60–7.64
(m, 3H), 7.20–7.48 (m, 6H), 6.86 (d, J = 2.1 Hz, 1H); 13C NMR
(75 MHz, CDCl3): d 136.3, 132.5, 131.4, 130.6, 129.1, 129.0,
127.5, 125.6, 125.3, 125.0, 124.0, 121.6, 121.2, 120.7, 119.4,
101.7; MS (EI, m/z): 243 [M]+; HRMS (ESI): Calcd. for C18H14N
[M+H]+: 244.11262; found: 244.11248.
6028 | RSC Adv., 2013, 3, 6022–6029
This journal is ß The Royal Society of Chemistry 2013