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The solvent was evaporated under reduced pressure. The
residue was puried by column chromatography over silica gel
using petroleum ether (65%): ethyl acetate (35%) mixture as an
eluent. The residue was recrystallized from diethyl ether giving
a white solid. In some cases the product was yellow or orange
solid or brown oil; for the additional purication it was washed
with eluent and then recrystallized with diethyl ether again or
puried by additional column chromatography until product
became white solid.
(2R*,3S*)-3-(4-Chlorophenyl)-1-(3-uorophenyl)spiro[azetidine-
2,30-indoline]-20,4-dione (29a). 1H NMR (400 MHz, DMSO-d6)
d ppm 10.93 (s, 1H), 7.70 (d, J ¼ 7.40 Hz, 1H), 7.40 (d, J ¼
8.56 Hz, 3H), 7.32–7.38 (m, 1H), 7.11–7.18 (m, 3H), 7.02 (d, J ¼
7.70 Hz, 1H), 6.92–6.99 (m, 2H), 6.59 – 6.66 (m, 1H), 5.41 (s, 1H).
13C NMR (101 MHz, DMSO-d6) d ppm 172.26, 164.45, 141.86,
137.85, 132.88, 131.81, 131.71, 131.11, 130.15, 130.08, 128.47,
124.85, 123.77, 122.90, 111.60, 111.05, 103.70, 103.44, 66.29,
64.56. HRMS (ESI) Calc for C22H15ClFN2O2 [M + H+]: 393.0801,
found: 393.0790.
(2R*,3R*)-3-(4-Chlorophenyl)-1-(3-uorophenyl)spiro[azetidine-
2,30-indoline]-20,4-dione (29b). 1H NMR (400 MHz, DMSO-d6)
d ppm 11.19 (s, 1H), 7.31–7.40 (m, 3H), 7.20–7.27 (m, 3H), 6.93–
7.02 (m, 3H), 6.69–6.78 (m, 2H), 6.63 (dd, J ¼ 8.10, 1.19 Hz, 1H),
5.13 (s, 1H). 13C NMR (101 MHz, DMSO-d6) d ppm 174.40,
164.16, 163.43, 161.00, 142.44, 137.78, 132.84, 131.78, 131.69,
130.93, 130.71, 130.41, 128.62, 125.50, 121.98, 120.74, 111.65,
111.62, 111.54, 111.33, 110.94, 103.83, 103.57, 65.51, 63.61.
HRMS (ESI) Calc for C22H15ClFN2O2 [M + H+]: 393.0801, found:
393.0790.
(2R*,3R*)-3-(4-Chlorophenyl)-1-(3-chlorophenyl)spiro[azetidine-
2,30-indoline]-20,4-dione (30b). 1H NMR (400 MHz, DMSO-d6)
d ppm 11.20 (s, 1H), 7.31–7.37 (m, 3H), 7.23–7.28 (m, 4H), 7.19
(td, J ¼ 8.07, 1.10 Hz, 1H), 6.97 (d, J ¼ 7.82 Hz, 1H), 6.69–6.79
(m, 3H), 5.13 (s, 1H). 13C NMR (101 MHz, DMSO-d6) d ppm
174.41, 164.20, 142.43, 137.57, 133.82, 132.86, 130.97, 130.75,
130.40, 128.62, 125.55, 124.50, 122.01, 120.68, 116.27, 114.18,
110.94, 65.46, 63.66. HRMS (ESI) Calc for C22H15Cl2N2O2 [M +
H+]: 409.0505, found: 409.0498.
(2R*,3S*)-3-(4-Chlorophenyl)-1-(3-bromophenyl)spiro[azetidine-
2,30-indoline]-20,4-dione (31a). 1H NMR (400 MHz, DMSO-d6)
d ppm 10.91 (s, 1H), 7.67 (d, J ¼ 7.27 Hz, 1H), 7.53 (d, J ¼
8.86 Hz, 2H), 7.37–7.43 (m, 3H), 7.16 (d, J ¼ 8.44 Hz, 2H), 7.12
(td, J ¼ 7.55, 0.67 Hz, 1H), 7.00 (d, J ¼ 7.70 Hz, 1H), 6.96 (d, J ¼
8.86 Hz, 2H), 5.37 (s, 1H). 13C NMR (101 MHz, DMSO-d6) d ppm
172.28, 164.20, 150.16, 141.82, 135.67, 132.80, 132.51, 130.99,
130.14, 130.12, 128.42, 124.75, 123.79, 122.82, 118.00, 116.22,
111.01, 66.11, 64.62. HRMS (ESI) Calc for C22H15BrClN2O2 [M +
H+]: 453.0000, found: 452.9981.
(2R*,3R*)-3-(4-Chlorophenyl)-1-(3-bromophenyl)spiro[azetidine-
2,30-indoline]-20,4-dione (31b). 1H NMR (400 MHz, DMSO-d6)
d ppm 11.20 (s, 1H), 7.42 (s, 1H), 7.32–7.36 (m, 2H), 7.30 (d, J ¼
6.42 Hz, 1H), 7.20–7.27 (m, 4H), 6.97 (d, J ¼ 7.76 Hz, 1H), 6.70–
6.79 (m, 3H), 5.13 (s, 1H). 13C NMR (101 MHz, DMSO-d6) d ppm
174.41, 164.18, 142.43, 137.68, 132.85, 131.77, 130.96, 130.75,
130.40, 128.61, 127.37, 125.56, 122.20, 120.67, 119.17, 114.48,
110.91, 65.43, 63.65. HRMS (ESI) Calc for C22H15BrClN2O2 [M +
H+]: 453.0000, found: 452.9984.
(2R*,3S*)-3-(4-Chlorophenyl)-1-(3-iodophenyl)spiro[azetidine-
2,30-indoline]-20,4-dione (32a). 1H NMR (400 MHz, DMSO-d6)
d ppm 10.94 (s, 1H), 7.69 (d, J ¼ 7.34 Hz, 1H), 7.59 (s, 1H), 7.46
(d, J ¼ 7.82 Hz, 1H), 7.40 (d, J ¼ 8.50 Hz, 3H), 7.16 (d, J ¼ 8.56 Hz,
2H), 7.07–7.13 (m, 2H), 7.01 (d, J ¼ 7.76 Hz, 1H), 6.76 (d, J ¼
8.31 Hz, 1H), 5.39 (s, 1H). 13C NMR (101 MHz, DMSO-d6) d ppm
172.26, 164.35, 141.81, 137.59, 132.99, 132.83, 131.62, 131.07,
130.12, 128.43, 124.88, 124.84, 123.75, 122.86, 114.74, 110.94,
95.39, 66.07, 64.47. HRMS (ESI) Calc for C22H15ClFN2O2 [M +
H+]: 500.9861, found: 500.9848.
(2R*,3R*)-3-(4-Chlorophenyl)-1-(3-iodophenyl)spiro[azetidine-
2,30-indoline]-20,4-dione (32b). 1H NMR (400 MHz, DMSO-d6)
d ppm 11.20 (s, 1H), 7.64 (br. s., 1H), 7.46 (d, J ¼ 7.64 Hz, 1H),
7.34 (d, J ¼ 8.01 Hz, 2H), 7.19–7.28 (m, 3H), 7.09 (t, J ¼ 7.92 Hz,
1H), 6.97 (d, J ¼ 7.64 Hz, 1H), 6.69–6.78 (m, 3H), 5.11 (s, 1H). 13
C
NMR (101 MHz, DMSO-d6) d ppm 174.46, 164.10, 161.77,
153.07, 142.42, 137.55, 133.20, 132.83, 131.59, 130.74, 130.44,
128.60, 125.54, 125.06, 121.97, 114.76, 110.87, 95.39, 65.32,
63.58. HRMS (ESI) Calc for C22H15ClFN2O2 [M + H+]: 500.9861,
found: 500.9845.
(2R*,3S*)-3-(4-Chlorophenyl)-1-(4-methoxyphenyl)spiro[azeti-
dine-2,30-indoline]-20,4-dione (33a). 1H NMR (400 MHz, DMSO-
d6) d ppm 10.83 (s, 1H), 7.64 (d, J ¼ 7.40 Hz, 1H), 7.35–7.40 (m,
3H), 7.18 (d, J ¼ 8.13 Hz, 2H), 7.10 (t, J ¼ 7.52 Hz, 1H), 6.96–7.00
(m, 3H), 6.86–6.90 (m, 2H), 5.28 (s, 1H), 3.66 (s, 3H). 13C NMR
(101 MHz, DMSO-d6) d ppm 172.71, 163.57, 156.07, 141.92,
132.70, 130.79, 130.56, 130.19, 129.86, 128.35, 124.62, 124.36,
122.70, 117.89, 114.76, 110.85, 66.15, 64.40, 55.28. HRMS (ESI)
Calc for C23H18ClN2O3[M + H+]: 405.1000, found: 405.0997.
(2R*,3R*)-3-(4-Chlorophenyl)-1-(4-methoxyphenyl)spiro[azeti-
dine-2,30-indoline]-20,4-dione (33b). 1H NMR (400 MHz, DMSO-
d6) d ppm 11.10 (s, 1H), 7.34 (d, J ¼ 8.50 Hz, 2H), 7.23 (d, J ¼
8.50 Hz, 2H), 7.18–7.21 (m, 1H), 6.87–7.00 (m, 5H), 6.69–6.73
(m, 2H), 5.01 (s, 1H), 3.66 (s, 3H). 13C NMR (101 MHz, DMSO-d6)
d ppm 174.89, 163.29, 156.17, 142.48, 132.66, 131.32, 130.88,
130.62, 129.80, 128.55, 125.34, 121.81, 121.31, 117.93, 114.73,
110.76, 68.25, 65.38, 55.25. HRMS (ESI) Calc for C23H18ClN2O3
[M + H+]: 405.1000, found: 405.1000.
(2R*,3S*)-3-(4-Chlorophenyl)-1-(m-tolyl)spiro[azetidine-2,30-
1
indoline]-20,4-dione (34a). H NMR (400 MHz, DMSO-d6) d ppm
10.87 (s, 1H), 7.64 (d, J ¼ 7.34 Hz, 1H), 7.36–7.42 (m, 3H), 7.14–
7.19 (m, 3H), 7.08–7.14 (m, 2H), 7.00 (d, J ¼ 7.76 Hz, 1H), 6.90 (d,
J ¼ 7.58 Hz, 1H), 6.58 (d, J ¼ 8.25 Hz, 1H), 5.32 (s, 1H), 2.21 (s,
3H). 13C NMR (101 MHz, DMSO-d6) d ppm 172.19, 163.85,
141.37, 138.74, 136.32, 132.48, 130.59, 129.92, 129.11, 128.13,
124.89, 124.38, 122.50, 116.81, 112.49, 110.55, 64.00, 59.53,
20.89. HRMS (ESI) Calc for C23H18ClN2O2 [M + H+]: 389.1051,
found: 389.1046.
(2R*,3S*)-3-(4-Chlorophenyl)-1-(p-tolyl)spiro[azetidine-2,30-
1
indoline]-20,4-dione (35a). H NMR (400 MHz, DMSO-d6) d ppm
10.86 (s, 1H), 7.63 (d, J ¼ 7.40 Hz, 1H), 7.37–7.41 (m, 3H), 7.17
(d, J ¼ 7.89 Hz, 2H), 7.10 (d, J ¼ 7.76 Hz, 3H), 7.00 (d, J ¼ 7.70 Hz,
1H), 6.93 (d, J ¼ 7.82 Hz, 2H), 5.31 (s, 1H), 2.19 (s, 3H). 13C NMR
(101 MHz, DMSO-d6) d ppm 172.68, 163.91, 141.87, 134.18,
133.75, 132.77, 131.42, 130.87, 130.49, 130.23, 129.92, 128.42,
128.21, 124.64, 124.36, 122.78, 116.19, 110.93, 66.02, 64.38,
14130 | RSC Adv., 2020, 10, 14122–14133
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