Page 7 of 10
New Journal of Chemistry
Please do not adjust margins
Journal Name
ARTICLE
1
2
3
4
R4. 1-(4-nitrophenyl)-1H-benzo[d]imidazole {C13H9N3O2} (77%, 132.80, 128.93, 128.22, 125.91, 122.10, 120.97, 120.03, 114.87,
DOI: 10.1039/D0NJ02568B
184mg). 1H NMR (400 MHz, CDCl3): δ 1H NMR (400 MHz, ) δ 8.44 (d, 114.69, 110.32, 102.85, 55.50 ppm.47
5
6
7
8
J = 8.9 Hz, 2H), 8.18 (s, 1H), 7.88-7.86 (m, 1H), 7.72 (d, J = 8.9 Hz, 2H), R11. 1-(4-nitrophenyl)-1H-indole {C14H10N2O2} (78%, 186mg). 1H
7.61 – 7.58 (m, 1H), 7.41 – 7.36 (m, 2H) ppm. 13C NMR (100 MHz, NMR (500 MHz, CDCl3) δ 8.41 (d, J = 9.0 Hz, 2H), 7.75 (d, J = 7.8 Hz,
CDCl3): δ = 146.37, 144.28, 141.58, 141.49, 132.66, 125.74, 124.48, 1H), 7.69 (d, J = 9.0 Hz, 3H), 7.41 (d, J = 3.4 Hz, 1H), 7.34 (t, J = 7.7 Hz,
9
123.62, 123.51, 121.03, 110.20 ppm.40
1H), 7.28 (t, J = 7.0 Hz, 1H), 6.82 (d, J = 3.4 Hz, 1H) ppm. 13C NMR (126
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
R5. 1-(pyridin-2-yl)-1H-benzo[d]imidazole {C12H9N3} (68%, 133mg). MHz, CDCl3) δ 145.15, 144.97, 135.19, 130.06, 127.04, 125.41,
1H NMR (500 MHz, CDCl3) δ 8.59 (d, J = 4.9 Hz, 1H), 8.58 (s, 1H), 8.05 123.35, 123.21, 121.61, 121.53, 110.41, 106.11 ppm.48
(d, J = 7.3 Hz, 1H), 7.87 (t, J = 7.6 Hz, 2H), 7.55 (d, J = 8.2 Hz, 1H), 7.40- R12. 1-(3-nitrophenyl)-1H-indole {C14H10N2O2} (69%, 164mg). 1H
7.33 (m, 2H), 7.28-7.27 (m, 1H) ppm. 13C NMR (126 MHz, CDCl3) δ NMR (500 MHz, CDCl3) δ 8.42 (t, J = 2.1 Hz, 1H), 8.23 (d, J = 7.0 Hz,
149.77, 149.34, 144.56, 141.22, 138.82, 132.02, 124.10, 123.18, 1H), 7.90 (d, J = 8.0 Hz, 1H), 7.74 (m, 2H), 7.62 (d, J = 7.7 Hz, 1H), 7.41
121.72, 120.51, 114.19, 112.56.43
(d, J = 3.3 Hz, 1H), 7.32 (t, J = 7.2 Hz, 1H), 7.29-7.25 (m, 1H), 6.80 (d,
R6. 1-(3-nitrophenyl)-1H-benzo[d]imidazole {C13H9N3O2} (66%, J = 3.3 Hz, 1H) ppm. 13C NMR (126 MHz, CDCl3) δ 149.11, 140.89,
158mg). 1H NMR (500 MHz, CDCl3) δ 8.40 (t, J = 2.1 Hz, 1H), 8.30 (m, 135.43, 130.53, 129.66, 129.52, 127.15, 123.17, 121.52, 121.19,
1H), 8.16 (s, 1H), 7.90 – 7.86 (m, 2H), 7.78 (t, J = 8.1 Hz, 1H), 7.56 – 120.75, 118.68, 109.96, 105.34 ppm.49
7.52 (m, 1H), 7.38 – 7.34 (m, 2H) ppm. 13C NMR (126 MHz, CDCl3) δ R13. 1-(naphthalen-2-yl)-1H-indole {C18H13N} (64%, 156mg). 1H NMR
149.16, 144.08, 141.61, 137.42, 132.99, 131.11, 129.32, 124.37, (500 MHz, CDCl3) δ 7.97 (d, J = 8.1 Hz, 2H), 7.76 (d, J = 7.9 Hz, 1H),
123.43, 122.45, 120.95, 118.61, 109.90 ppm.44
7.61 – 7.53 (m, 3H), 7.46 (d, J = 8.0 Hz, 1H), 7.44 – 7.39 (m, 1H), 7.37
R7. 1-(thiophen-2-yl)-1H-benzo[d]imidazole {C11H8N2S} (63%, (d, J = 3.2 Hz, 1H), 7.21 – 7.16 (m, 1H), 7.16 – 7.11 (m, 1H), 7.05 – 6.99
126mg). 1H NMR (400 MHz, CDCl3) 1H NMR (500 MHz, CDCl3) δ 8.08 (m, 1H), 6.78-6.77 (m, 1H) ppm. 13C NMR (126 MHz, CDCl3) δ 138.03,
(s, 1H), 7.87 – 7.84 (m, 1H), 7.58 – 7.54 (m, 1H), 7.37 – 7.34 (m, 2H), 136.09, 134.48, 130.60, 129.78, 128.46, 128.24, 126.93, 126.63,
7.32 (d, J = 5.5 Hz, 1H), 7.17 (d, J = 3.7 Hz, 1H), 7.13 – 7.10 (m, 1H) 125.49, 125.14, 123.41, 122.13, 120.90, 120.10, 110.82, 102.90
ppm. 13C NMR (126 MHz, CDCl3) δ 143.54, 143.09, 137.08, 134.71, ppm.50
126.41, 124.13, 123.42, 123.20, 121.92, 120.58, 110.52 ppm.45
Conflicts of interest
1
R8. 1-phenyl-1H-indole {C14H11N} (87%, 168mg). H NMR (500 MHz,
There are no conflicts to declare.
CDCl3) δ 7.76 (d, J = 7.7 Hz, 1H), 7.64 (d, J = 8.2 Hz, 1H), 7.57 (d, J =
Acknowledgements
4.6 Hz, 4H), 7.43-7.40 (m, 2H), 7.29 (t, J = 7.6 Hz, 1H), 7.24 (t, J = 7.4
KG is thankful to CSIR, New Delhi, India for financial assistance No.
Hz, 1H), 6.75 (d, J = 3.2 Hz, 1H) ppm. 13C NMR (126 MHz, CDCl3) δ
01(2942)/18/EMR-II dated 01-05-2018). SK and VK are thankful to
139.84, 135.87, 129.57, 129.32, 127.91, 126.41, 124.36, 122.32,
CSIR, KM is thankful to UGC, AR and AM are thankful to MHRD, India
121.10, 120.33, 110.47, 103.55 ppm.46
for financial assistance.
R9. 1-(p-tolyl)-1H-indole {C15H13N} (83%, 172mg). 1H NMR (500 MHz,
Notes and references
CDCl3) δ 7.71 (d, J = 8.4 Hz, 1H), 7.56 (d, J = 8.2 Hz, 1H), 7.42 (d, J =
1 R. K. Kumar and T. Punniyamurthy, RSC Advances, 2012, 2, 4616-
8.3 Hz, 2H), 7.34 (m, 3H), 7.25 – 7.22 (m, 1H), 7.19 (t, J = 7.4 Hz, 1H),
4619.
6.70 (d, J = 3.9 Hz, 1H), 2.47 (s, 3H) ppm. 13C NMR (126 MHz, CDCl3)
2 D. F. Tardiff, N. T. Jui, V. Khurana, M. A. Tambe, M. L. Thompson, C.
δ 137.31, 136.32, 136.01, 130.12, 129.17, 128.05, 124.34, 122.18,
Y. Chung, H. B. Kamadurai, H. T. Kim, A. K. Lancaster, K. A. Caldwell,
G. A. Caldwell, J. C. Rochet, S. L. Buchwald and S. Lindquist, Science,
2013, 342, 979-983.
121.03, 120.16, 110.49, 103.17, 21.02 ppm.47
R10. 1-(4-methoxyphenyl)-1H-indole {C15H13NO} (84%, 187mg). 1H
NMR (500 MHz, CDCl3) δ 7.78 (d, J = 7.6 Hz, 1H), 7.56 (d, J = 8.1 Hz,
1H), 7.48 (d, J = 8.9 Hz, 2H), 7.36 (d, J = 3.2 Hz, 1H), 7.30 (d, J = 8.1 Hz,
1H), 7.26 (d, J = 7.9 Hz, 1H), 7.10 (d, J = 8.9 Hz, 2H), 6.75 (d, J = 3.8 Hz,
1H), 3.94 (s, 3H) ppm. 13C NMR (126 MHz, CDCl3) δ 158.20, 136.30,
3 S. L. Cincotta and J. S. Rodefer. Neuropsychiatr. Dis. Treat., 2010,
6, 429-441.
4 W. Zhang and J. M. Ready, Nat. Prod. Rep., 2017, 34, 1010-1034.
5 Q. Shen and J. F. Hartwig, Org. Lett., 2008, 10, 4109-4112.
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 7
Please do not adjust margins