RSC Advances
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and the supernatant was sucked off with a syringe. The solid (Z)-2-(5-((4-(4-(Diphenylamino)phenyl)naphthalen-1-yl)
was washed with 1 mL of AA and 4 times with 4 mL portions of methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid (5b)
water in the same manner. The obtained product was dried in
1
Orange crystalline solid (148 mg, 0.258 mmol). Yield: 90%. H
ꢁ
an oven at 110 C overnight. In some cases the product was
puried by subsequent recrystallization from 2-propanol.
NMR (300 MHz, DMSO-d
6
) d 8.55 (s, 1H), 8.26 (d, J ¼ 8.3 Hz, 1H),
.02 (d, J ¼ 8.3 Hz, 1H), 7.79 (d, J ¼ 7.6 Hz, 1H), 7.75–7.61 (m,
H), 7.59 (d, J ¼ 7.6 Hz, 1H), 7.45–7.31 (m, 6H), 7.17–7.04 (m,
8
2
8
1
1
1
1
3
6
H), 4.78 (s, 2H). C NMR (151 MHz, DMSO-d ) d 193.84,
0
0
(
Z)-5-((4 -(Diphenylamino)-(1,1 -biphenyl)-4-yl)methylene)-2-
thioxothiazolidin-4-one (4a)
Brick-red crystalline solid (128 mg, 0.276 mmol). Yield: 96%. H
NMR (300 MHz, DMSO-d
67.51, 166.03, 147.34, 147.06, 142.95, 132.76, 131.79, 131.32,
30.97, 130.73, 129.89, 129.21, 127.82, 127.41, 127.18, 126.79,
26.73, 124.95, 124.73, 124.09, 123.78, 122.29, 45.22. IR (ATR,
1
ꢀ
1
6
) d 7.79 (d, J ¼ 8.2 Hz, 2H), 7.71–7.55
13
nmax, cm ): 1725 (C]O), 1708 (C]O), 1062 (C]S). MS (ESI-
ꢀ
(
m, 5H), 7.33 (t, J ¼ 7.8 Hz, 4H), 7.14–6.95 (m, 8H). C NMR (75
HRMS): calculated for [C34
71.1137 (error 3.3 ppm).
H
23
N
2
O
3
S
2
]
571.1156, measured
6
MHz, DMSO-d ) d 195.64, 169.62, 147.75, 146.89, 141.66, 132.02,
5
1
1
31.50, 131.42, 129.84, 127.94, 126.90, 124.86, 124.72, 123.82,
ꢀ
1
22.64. IR (ATR, nmax, cm ): 1689 (C]O), 1068 (C]S). MS (ESI-
(
Z)-2-(5-((10-(4-(Diphenylamino)phenyl)anthracen-9-yl)
ꢀ
HRMS): calculated for [C28
63.0947 (error 0.6 ppm).
H
19
N
2
OS
2
]
463.0944, measured
methylene)-4-oxo-2-thioxothiazolidin-3-yl)acetic acid (5c)
4
1
Red crystalline solid (159 mg, 0.255 mmol). Yield: 89%. H NMR
(
(
300 MHz, DMSO-d
d, J ¼ 8.7 Hz, 2H), 7.69–7.58 (m, 2H), 7.59–7.48 (m, 2H), 7.38 (t,
6
) d 8.83 (s, 1H), 8.06 (d, J ¼ 8.7 Hz, 2H), 7.76
(
Z)-5-((4-(4-(Diphenylamino)phenyl)naphthalen-1-yl)
J ¼ 7.8 Hz, 4H), 7.28 (d, J ¼ 8.5 Hz, 2H), 7.23–7.07 (m, 8H), 4.79
methylene)-2-thioxothiazolidin-4-one (4b)
1
3
(s, 2H). C NMR (151 MHz, DMSO-d ) d 193.63, 167.57, 165.05,
6
Dark-brown crystalline solid (139 mg, 0.270 mmol). Yield: 94%.
1
1
1
1
6
47.18, 139.73, 132.57, 131.94, 131.10, 130.85, 129.92, 129.53,
1
H NMR (300 MHz, DMSO-d ) d 8.31 (s, 1H), 8.23 (d, J ¼ 8.4 Hz,
6
27.89, 127.51, 127.27, 126.99, 126.31, 125.30, 124.76, 123.75,
1
6
1
1
1
1
H), 8.01 (d, J ¼ 8.1 Hz, 1H), 7.75–7.53 (m, 4H), 7.45–7.30 (m,
ꢀ1
22.25, 45.29. IR (ATR, nmax, cm ): 1727 (C]O), 1713 (C]O),
1
3
H), 7.18–7.04 (m, 8H). C NMR (151 MHz, DMSO-d ) d 196.17,
ꢀ
6
25 2 3 2
056 (C]S). MS (ESI-HRMS): calculated for [C38H N O S ]
68.97, 147.16, 146.97, 142.33, 132.77, 131.66, 131.19, 130.85,
29.75, 129.34, 128.60, 128.17, 127.52, 127.17, 126.68, 126.63,
21.1312, measured 621.1289 (error 3.7 ppm).
ꢀ
1
26.57, 124.58, 123.93, 123.60, 122.26. IR (ATR, nmax, cm ):
0
0
(
Z)-5-((4 -(Diphenylamino)-(1,1 -biphenyl)-4-yl)methylene)-2-
thioxoimidazolidin-4-one (6a)
Orange crystalline solid (92 mg, 0.206 mmol). Yield: 72%. H
NMR (300 MHz, DMSO-d ) d 12.38 (s, 1H), 12.20 (s, 1H), 7.80 (d, J
8.2 Hz, 2H), 7.67 (t, J ¼ 8.2 Hz, 4H), 7.33 (t, J ¼ 7.8 Hz, 4H),
683 (C]O), 1073 (C]S). MS (ESI-HRMS): calculated for
ꢀ
[C
32
H
21
N
2
OS
2
]
513.1101, measured 513.1103 (error 0.4 ppm).
1
6
¼
(
Z)-5-((10-(4-(Diphenylamino)phenyl)anthracen-9-yl)
1
3
7
.13–6.97 (m, 8H), 6.51 (s, 1H). C NMR (151 MHz, DMSO-d
6
)
methylene)-2-thioxothiazolidin-4-one (4c)
Orange powder (145 mg, 0.257 mmol). Yield: 90%. H NMR (300
MHz, DMSO-d
) d 8.52 (s, 1H), 8.10 (d, J ¼ 8.6 Hz, 2H), 7.75 (d, J
8.7 Hz, 2H), 7.68–7.58 (m, 2H), 7.58–7.47 (m, 2H), 7.39 (t, J ¼
d 179.17, 166.05, 147.45, 147.05, 140.32, 132.81, 131.06, 129.88,
1
127.83, 127.61, 126.46, 124.59, 123.73, 123.05, 111.63. IR (ATR,
6
ꢀ1
nmax, cm ): 1720 (C]O), 1080 (C]S). MS (ESI-HRMS): calcu-
¼
ꢀ
lated for [C28
ppm).
H
20
N
3
OS] 446.1333, measured 446.1321 (error 2.7
1
3
7
.9 Hz, 4H), 7.30 (d, J ¼ 8.5 Hz, 2H), 7.24–7.08 (m, 8H). C NMR
(151 MHz, DMSO-d ) d 147.24, 132.02, 129.97, 129.56, 127.88,
6
1
27.42, 127.04, 126.27, 125.58, 124.76, 124.70, 123.78, 122.36. IR
(
Z)-5-((4-(4-(Diphenylamino)phenyl)naphthalen-1-yl)
methylene)-2-thioxoimidazolidin-4-one (6b)
Yellow crystalline solid (122 mg, 0.245 mmol). Yield: 86%. H
NMR (300 MHz, DMSO-d
) d 12.34 (s, 2H), 8.15 (d, J ¼ 8.2 Hz,
H), 7.98 (d, J ¼ 7.9 Hz, 1H), 7.85 (d, J ¼ 7.5 Hz, 1H), 7.70–7.53
(m, 2H), 7.49 (d, J ¼ 7.5 Hz, 1H), 7.45–7.31 (m, 6H), 7.17–7.05
ꢀ1
(ATR, nmax, cm ): 1734 (C]O), 1068 (C]S). MS (ESI-HRMS):
ꢀ
calculated for [C36
H
23
N
2
OS
2
]
563.1257, measured 563.1259
1
(error 0.4 pm).
6
1
0
0
(
Z)-2-(5-((4 -(Diphenylamino)-(1,1 -biphenyl)-4-yl)methylene)-
1
3
4
-oxo-2-thioxothiazolidin-3-yl)acetic acid (5a)
Red powder (140 mg, 0.268 mmol). Yield: 94%. H NMR (300
MHz, DMSO-d
) d 7.90 (s, 1H), 7.84 (d, J ¼ 8.3 Hz, 2H), 7.70 (dd, J
8.5, 6.3 Hz, 4H), 7.34 (t, J ¼ 7.8 Hz, 4H), 7.15–7.04 (m, 6H),
6
(m, 9H). C NMR (151 MHz, DMSO-d ) d 130.99, 129.93, 124.64,
123.72. IR (ATR, nmax, cm ): 1714 (C]O), 1087 (C]S). MS (ESI-
HRMS): calculated for [C H N OS] 496.1489, measured
4
ꢀ
1
1
ꢀ
3
2
22 3
6
96.1465 (error 4.8 ppm).
¼
1
3
7
.02 (d, J ¼ 8.6 Hz, 2H), 4.74 (s, 2H). C NMR (151 MHz, DMSO)
(
Z)-5-((10-(4-(Diphenylamino)phenyl)anthracen-9-yl)
d 193.21, 167.49, 166.56, 147.89, 146.88, 142.17, 133.79, 131.89,
methylene)-2-thioxoimidazolidin-4-one (6c)
1
1
1
5
31.76, 131.28, 129.87, 128.01, 127.01, 124.80, 123.90, 122.56,
ꢀ
1
21.12, 45.19. IR (ATR, nmax, cm ): 1722 (C]O), 1701 (C]O), The pure product was obtained aer recrystallization from 2-
ꢀ
056 (C]S). MS (ESI-HRMS): calculated for [C30
H
21
N
2
O
3
S
2
]
propanol. Red crystalline solid (116 mg, 0.212 mmol). Yield:
74%. H NMR (300 MHz, DMSO-d ) d 12.37 (s, 1H), 11.67 (s, 1H),
6
1
21.0999, measured 521.0994 (error 1.0 ppm).
39378 | RSC Adv., 2019, 9, 39367–39380
This journal is © The Royal Society of Chemistry 2019