Paper
RSC Advances
1
3
biscyclohexyldisulfane (2i) (69.1 mg, 0.30 mmol). Purication by 7.8 Hz, 1H), 7.07 (dd, J ¼ 7.9, 1.0 Hz, 1H). C NMR (100 MHz,
PTLC on silica gel (n-hexane/EtOAc: 40/1) yielded (3i) in 65% CDCl ): d ¼ 147.4, 146.4, 140.7, 136.3, 135.3, 135.22, 135.16,
3
1
(
58.4 mg) as a yellow oil. H NMR (400 MHz, CDCl ): d ¼ 8.83 (d, 129.9, 129.1, 128.6, 127.44, 127.37, 127.2, 125.62, 125.56, 124.6,
3
J ¼ 4.8 Hz, 2H), 8.04 (d, J ¼ 7.7 Hz, 1H), 8.00 (d, J ¼ 7.7 Hz, 1H), 121.0. HRMS m/z (EI) calcd for [C H NS]: 287.0769, found:
1
9
13
7
.88 (d, J ¼ 8.2 Hz, 1H), 7.58 (d, J ¼ 7.6 Hz, 1H), 7.41 (t, J ¼ 7.7 287.0765.
Hz, 1H), 7.31 (dd, J ¼ 15.5, 7.8 Hz, 2H), 7.24–7.17 (m, 1H), 2.90
10-((4-Methylphenyl)thio)benzo[h]quinoline
general method was followed using benzo[h]quinoline (4) (44.8
(5b).
The
1
3
(
t, J ¼ 9.7 Hz, 1H), 1.64–1.46 (m, 5H), 1.14–1.02 (m, 5H).
C
NMR (100 MHz, CDCl
1
1
3
): d ¼ 159.1, 158.4, 141.8, 141.4, 132.9, mg, 0.25 mmol) and diphenyl 1,2-bis(4-methylphenyl)disulfane
26.6, 126.3, 124.9, 122.1, 121.8, 120.0, 120.0, 119.3, 118.4, (2b) (73.9 mg, 0.30 mmol). Purication by PTLC on silica gel (n-
11.8, 48.4, 33.0, 25.8, 25.6. HRMS m/z (EI) calcd for hexane/EtOAc: 20/1) yielded (5b) in 75% (56.5 mg) as a white
1
[
C H N S]: 359.1456, found: 359.1454.
solid. H NMR (400 MHz, CDCl ): d ¼ 9.17 (dd, J ¼ 4.3, 1.6 Hz,
2
2
21
3
3
1
-(Propylthio)-9-(pyrimidin-2-yl)-9H-carbazole
(3j).
The 1H), 8.22 (d, J ¼ 8.0 Hz, 1H), 7.81 (d, J ¼ 8.5 Hz, 1H), 7.71 (d, J ¼
general method was followed using 9-(pyrimidin-2-yl)-9H- 8.8 Hz, 1H), 7.65 (d, J ¼ 7.8 Hz, 1H), 7.62–7.54 (m, 3H), 7.39 (t, J
carbazole (1) (61.3 mg, 0.25 mmol) and 1,2-bispropyldisulfane ¼ 7.8 Hz, 1H), 7.30 (d, J ¼ 7.9 Hz, 2H), 7.07 (dd, J ¼ 7.9, 1.0 Hz,
1
3
(
2j) (45.1 mg, 0.30 mmol). Purication by PTLC on silica gel (n- 1H), 2.45 (s, 3H). C NMR (100 MHz, CDCl
3
): d ¼ 147.5, 146.4,
hexane/EtOAc: 50/1) yielded (3j) in 77% (61.5 mg) as a yellow oil. 141.0, 139.1, 136.3, 135.3, 135.1, 131.5, 130.6, 128.6, 127.4,
1
H NMR (400 MHz, CDCl
3
): d ¼ 8.827 (d, J ¼ 4.9 Hz, 2H), 8.04 127.3127.2, 125.6, 125.4, 124.5, 121.0, 21.42. HRMS m/z (EI)
(
dd, J ¼ 11.9, 7.9 Hz, 2H), 7.97 (d, J ¼ 7.6 Hz, 1H), 7.55 (d, J ¼ 7.4 calcd for [C H NS]: 301.0925, found: 301.0920.
2
0
15
Hz, 1H), 7.43 (dd, J ¼ 11.7, 4.5 Hz, 1H), 7.36–7.31 (m, 2H), 7.24
10-((4-Chlorophenyl)thio)benzo[h]quinoline
(5c).
The
(
dd, J ¼ 10.0, 5.1 Hz, 1H), 2.75 (t, J ¼ 7.3 Hz, 2H), 1.45–1.36 (m, general method was followed using benzo[h]quinoline (4) (44.8
13
2
1
1
H), 0.84 (t, J ¼ 7.3 Hz, 3H). C NMR (100 MHz, CDCl ): d ¼ mg, 0.25 mmol) and 1,2-bis(4-chlorophenyl)disulfane (2c) (86.3
3
59.0, 158.5, 141.4, 140.6, 130.2, 126.8, 126.5, 125.2, 122.5, mg, 0.30 mmol). Purication by PTLC on silica gel (n-hexane/
1
22.3, 122.1, 120.1, 118.5, 118.3, 112.3, 38.5, 22.6, 13.3. HRMS EtOAc: 10/1) yielded (5c) in 83% (66.8 mg) as a white solid. H
m/z (EI) calcd for [C19
-(Benzylthio)-9-(pyrimidin-2-yl)-9H-carbazole (3k). The 7.8 Hz, 1H), 7.81 (d, J ¼ 8.8 Hz, 1H), 7.73–7.61 (m, 4H), 7.57 (dd,
general method was followed using 9-(pyrimidin-2-yl)-9H- J ¼ 7.9, 4.2 Hz, 1H), 7.46–7.40 (m, 3H), 7.05 (d, J ¼ 7.8 Hz, 1H).
H
17
N
3
S]: 319.1143, found: 319.1142.
NMR (400 MHz, CDCl
3
): d ¼ 9.15 (d, J ¼ 3.1 Hz, 1H), 8.22 (d, J ¼
1
1
3
carbazole (1) (61.3 mg, 0.25 mmol) and 1,2-bisbenzylphenyl
disulfane (2k) (73.9 mg, 0.30 mmol). Purication by PTLC on 135.3, 135.1, 133.9, 130.1, 130.0, 128.6, 127.4, 127.4, 127.2,
silica gel (n-hexane/EtOAc: 20/1) yielded (3k) in 30% (27.6 mg) as 125.7, 125.5, 124.8, 121.1. HRMS m/z (EI) calcd for [C19 12ClNS]:
C NMR (100 MHz, CDCl ): d ¼ 147.3, 146.4, 140.0, 137.5,
3
H
1
a white solid. H NMR (400 MHz, CDCl
3
): d ¼ 8.83 (d, J ¼ 4.8 Hz, 321.0379, found: 321.0374.
2
H), 8.04–8.00 (m, 2H), 7.96 (dd, J ¼ 7.7, 1.0 Hz, 1H), 7.47–7.41 10-((4-Methoxyphenyl)thio)benzo[h]quinoline (5d). The
(
7
m, 2H), 7.33 (td, J ¼ 7.5, 0.9 Hz, 1H), 7.26–7.24 (m, 1H), 7.21– general method was followed using benzo[h]quinoline (4) (44.8
1
3
.17 (m, 4H), 7.11–7.09 (m, 2H), 3.94 (s, 2H). C NMR (100 MHz, mg, 0.25 mmol) and 1,2-bis(4-methoxyphenyl)disulfane (2e)
CDCl ): d ¼ 158.9, 158.5, 141.4, 140.3, 137.4, 130.9, 129.0, 128.3, (83.5 mg, 0.30 mmol). Purication by PTLC on silica gel (n-
3
1
1
3
27.0, 126.8, 126.7, 125.1, 122.5, 122.1, 121.9, 120.1, 119.0, hexane/EtOAc: 20/1) yielded (5d) in 90% (71.3 mg) as a yellow
1
18.4, 112.4, 41.3. HRMS m/z (EI) calcd for [C H N S]: solid. H NMR (400 MHz, CDCl ): d ¼ 9.16 (dd, J ¼ 4.4, 1.8 Hz,
2
3
17
3
3
67.1143, found: 367.1141.
Methyl-3-((9-(pyrimidin-2-yl)-9H-carbazol-1-yl)thio)propano-
1H), 8.16 (dd, J ¼ 8.0, 1.7 Hz, 1H), 7.76 (d, J ¼ 8.8 Hz, 1H), 7.62
(m, 4H), 7.51 (dd, J ¼ 8.0, 4.4 Hz, 1H), 7.38 (t, J ¼ 7.8 Hz, 1H),
ate (3l). The general method was followed using 9-(pyrimidin-2- 7.06 (dd, J ¼ 7.9, 0.8 Hz, 1H), 7.00 (d, J ¼ 8.7 Hz, 2H), 3.83 (s,
1
3
yl)-9H-carbazole (1) (61.3 mg, 0.25 mmol) and disul- 3H). C NMR (100 MHz, CDCl
3
): d ¼ 159.4, 146.4, 145.3, 140.4,
fanediylbis(methylene) dipropionate (2l) (71.5 mg, 0.30 mmol). 136.8, 134.1, 134.1, 127.5, 126.3, 126.2, 126.1, 124.7, 124.5,
Purication by PTLC on silica gel (n-hexane/EtOAc: 40/1) yielded 124.1, 123.4, 119.9, 114.3, 54.3. HRMS m/z (EI) calcd for
1
(
3l) in 39% (35.4 mg) as a yellow oil. H NMR (400 MHz, CDCl ): [C H NOS]: 317.0874, found: 317.0870.
3
20 15
d ¼ 8.85 (d, J ¼ 4.8 Hz, 2H), 8.06–7.99 (m, 3H), 7.57 (dd, J ¼ 7.6,
10-(Propylthio)benzo[h]quinoline (5e). The general method
.0 Hz, 1H), 7.47–7.40 (m, 1H), 7.37–7.31 (m, 2H), 7.24 (t, J ¼ 4.9 was followed using benzo[h]quinoline (4) (44.8 mg, 0.25 mmol)
1
Hz, 1H), 3.56 (s, 3H), 3.00 (t, J ¼ 7.5 Hz, 2H), 2.33 (t, J ¼ 7.5 Hz, and 1,2-bispropyldisulfane (2j) (45.1 mg, 0.30 mmol). Purica-
1
3
2
1
1
H). C NMR (100 MHz, CDCl
3
): d ¼ 172.2, 159.0, 158.5, 141.4, tion by PTLC on silica gel (n-hexane/EtOAc: 20/1) yielded (5e) in
1
41.0, 130.9, 126.9, 126.7, 125.0, 122.7, 122.2, 120.6, 120.2, 85% (53.8 mg) as a yellow oil. H NMR (400 MHz, CDCl
3
): d ¼
19.3, 118.4, 112.4, 51.7, 34.2, 31.4. HRMS m/z (EI) calcd for 9.13 (dd, J ¼ 4.4, 1.8 Hz, 1H), 8.15 (d, J ¼ 7.9 Hz, 1H), 7.78 (d, J ¼
[
C H N O S]: 363.1041, found: 363.1034.
8.7 Hz, 1H), 7.66 (dd, J ¼ 9.1, 5.1 Hz, 2H), 7.61 (d, J ¼ 4.8 Hz,
2
0
17 3 2
1
0-(Phenylthio)benzo[h]quinoline (5a). The general method 2H), 7.50 (dd, J ¼ 8.0, 4.4 Hz, 1H), 3.02 (t, J ¼ 7.5, 2H), 1.96–1.90
1
3
was followed using benzo[h]quinoline (4) (44.8 mg, 0.25 mmol) (m, 2H), 1.17 (t, J ¼ 7.4 Hz, 3H). C NMR (100 MHz, CDCl ): d ¼
3
and diphenyl disulde (2a) (65.5 mg, 0.30 mmol). Purication 147.4, 146.3, 139.6, 135.2, 135.0, 128.6, 128.0, 127.3, 127.0,
by PTLC on silica gel (n-hexane/EtOAc: 10/1) yielded (5a) in 86% 125.6, 124.0, 123.0, 120.7, 35.6, 21.4, 14.3. HRMS m/z (EI) calcd
10h
1
(
9
7
61.8 mg) as a white thick oil.
H NMR (400 MHz, CDCl
.14 (dd, J ¼ 4.4, 1.8 Hz, 1H), 8.12 (dd, J ¼ 8.0, 1.6 Hz, 1H), 7.74–
.69 (m, 3H), 7.62–7.57 (m, 2H), 7.50–7.41 (m, 4H), 7.35 (t, J ¼ method was followed using 1-(pyrimidin-2-yl)-1H-indole (6)
3
): d ¼ for [C16
H15NS]: 253.0925 found: 253.0927.
2-(Phenylthio)-1-(pyrimidin-2-yl)-1H-indole (7a). The general
This journal is © The Royal Society of Chemistry 2015
RSC Adv., 2015, 5, 39358–39365 | 39363