Page 5 of 7
RSC Advances
DOI: 10.1039/C5RA09478J
13CNMR (101 MHz, DMSO) δ 193.4, 146.0, 138.4, 136.8, 134.9,
7.99 (s, 4H), 7.60 (s, 3H), 7.16 (s, 5H), 6.71 (s, 1H), 5.47 (s, 1H),
3.97 (d, J = 35.0 Hz, 1H), 2.80 (d, J = 16.3 Hz, 1H), 2.02 (d, J =
16.9 Hz, 1H), 0.97 (d, J = 42.4 Hz, 6H). 13CNMR (101 MHz,
DMSO) δ 193.5, 146.2, 135.0, 133.1, 132.7, 132.0, 129.4, 128.8,
70 128.4, 128.2, 127.6, 127.5, 127.4, 126.9, 126.6, 119.7, 105.4,
68.1, 47.3, 45.7, 26.3, 25.9. HRMS (ESI-TOF) Calcd
forC26H24NO2+ ([M+H]+) 382.1807. Found 382.1834.
132.1, 130.2, 128.7, 128.5, 128.2, 127.5, 119.5, 105.2, 68.0, 47.2,
+
26.4, 25.9, 21.1. HRMS (ESI-TOF) Calcd for C23H24NO2
([M+H] +) 346.1807. Found 346.1811.
5
1-(4-bromophenyl)-7-hydroxy-6,6-dimethyl-2-phenyl-6,7-
dihydro-1H-indol-4(5H)-one(3b): yellow solid (112 mg, 55%).
m. p.: 153ꢀ155 ºC. IR (neat, ν, cmꢀ1): 3372, 2958, 1649, 1600,
1522, 763, 696, 673 cmꢀ1. 1HNMR (400 MHz, DMSO) δ 7.66 (d,
J = 5.1 Hz, 2H), 7.33 – 7.17 (m, 4H), 7.12 (d, J = 6.8 Hz, 3H),
2-(4-bromophenyl)-7-hydroxy-6,6-dimethyl-1-(p-tolyl)-6,7-
dihydro-1H-indol-4(5H)-one(3h): yellow solid (121 mg, 57%).
10 6.64 (s, 1H), 5.45 (d, J = 7.3 Hz, 1H), 3.89 (d, J = 7.1 Hz, 1H), 75 m. p.: 179ꢀ181ºC. IR (neat, ν, cmꢀ1): 3354, 2963, 2934, 1672,
1
2.76 (d, J = 16.3 Hz, 1H), 2.00 (d, J = 16.0 Hz, 1H), 1.03 (s, 3H),
0.89 (s, 3H). 13CNMR (101 MHz, DMSO) δ 193.4, 145.8, 136.8,
132.7, 131.7, 130.6, 128.9, 128.6, 127.7, 122.0, 119.8, 105.5,
68.0, 47.3, 26.2, 25.9. HRMS (ESI-TOF) Calcd for
15 C22H21BrNO2+ ([M+H]+) 410.0756. Found 410.0760.
1644, 1545, 743, 708, 661 cmꢀ1. HNMR (400 MHz, DMSO) δ
7.49 – 7.18 (m, 5H), 7.05 (d, J = 8.1 Hz, 3H), 6.69 (s, 1H), 5.42
(d, J = 6.6 Hz, 1H), 3.85 (s, 1H), 2.78 (d, J = 16.4 Hz, 1H), 2.36
(s, 3H), 1.99 (d, J = 16.4 Hz, 1H), 1.03 (s, 3H), 0.87 (s, 3H).
80 13CNMR (101 MHz, DMSO) δ 193.4, 146.3, 138.5, 135.5, 134.6,
131.7, 131.3, 130.4, 130.3, 128.2, 120.9, 119.6, 105.7, 68.0, 47.2,
+
26.4, 25.8, 21.2. HRMS (ESI-TOF) Calcd for C23H23BrNO2
1-(4-chlorophenyl)-7-hydroxy-6,6-dimethyl-2-phenyl-6,7-
dihydro-1H-indol-4(5H)-one(3c): yellow solid (119 mg, 65%).
m. p.: 139ꢀ141 ºC. IR (neat, ν, cmꢀ1): 2955, 2852, 1726, 1633,
1556, 762, 695, 638 cmꢀ1. 1HNMR (400 MHz, DMSO) δ 7.66 (d,
([M+H]+) 424.0912. Found 424.0902.
2-(4-chlorophenyl)-7-hydroxy-6,6-dimethyl-1-(p-tolyl)-6,7-
20 J = 5.1 Hz, 2H), 7.35 – 7.01 (m, 7H), 6.64 (s, 1H), 5.45 (d, J = 85 dihydro-1H-indol-4(5H)-one(3i): yellow solid (144 mg, 76%).
7.3 Hz, 1H), 3.89 (d, J = 7.1 Hz, 1H), 2.76 (d, J = 16.3 Hz, 1H),
2.00 (d, J = 16.0 Hz, 1H), 1.03 (s, 3H), 0.89 (s, 3H). 13CNMR
(101 MHz, CDCl3) δ 194.1, 144.0, 137.6, 135.8, 134.4, 131.3,
m. p.: 187ꢀ189 ºC. IR (neat, ν, cmꢀ1): 3264, 2963, 1673, 1645,
1555, 749, 720, 657 cmꢀ1. 1HNMR (400 MHz, DMSO) δ 7.28 (d,
J = 8.5 Hz, 5H), 7.11 (d, J = 8.5 Hz, 3H), 6.68 (s, 1H), 5.41 (d, J
= 7.3 Hz, 1H), 3.84 (d, J = 7.2 Hz, 1H), 2.77 (d, J = 16.4 Hz, 1H),
90 2.36 (s, 3H), 1.99 (d, J = 16.4 Hz, 1H), 1.03 (s, 3H), 0.87 (s, 3H).
13CNMR (101 MHz, DMSO) δ 193.4, 146.2, 138.5, 135.5, 134.6,
129.5, 129.2, 128.5, 128.4, 127.5, 120.1, 105.9, 69.3, 46.8, 39.5,
+
25 29.7, 25.8, 16.3. HRMS (ESI-TOF) Calcd for C22H21ClNO2
([M+H] +) 366.1261. Found 366.1262.
132.3, 131.0, 130.3, 130.1, 128.8, 128.2, 119.5, 105.7, 68.0, 47.2,
+
26.4, 25.8, 21.2. HRMS (ESI-TOF) Calcd forC23H23ClNO2
7-hydroxy-1-(4-methoxyphenyl)-6,6-dimethyl-2-phenyl-6,7-
([M+H]+) 380.1417. Found 380.1419.
dihydro-1H-indol-4(5H)-one(3d): yellow solid (130 mg, 72%).
m. p.: 149ꢀ151 ºC. IR (neat, ν, cmꢀ1): 3068, 2963, 2873, 1719,
1
30 1606, 741, 724, 691 cmꢀ1. HNMR (400 MHz, DMSO) δ 7.29 –
95
2-(3-chlorophenyl)-7-hydroxy-6,6-dimethyl-1-(p-tolyl)-6,7-
dihydro-1H-indol-4(5H)-one(3j): yellow solid (110 mg, 58%).
m. p.: 165ꢀ167 ºC. IR (neat, ν, cmꢀ1): 2957, 2931, 1639, 1597,
1567, 726, 690, 663 cmꢀ1. 1HNMR (400 MHz, DMSO) δ 7.23 (dd,
J = 26.7, 21.4 Hz, 7H), 7.03 (d, J = 4.3 Hz, 1H), 6.75 (s, 1H),
7.15 (m, 4H), 7.12 (d, J = 6.7 Hz, 2H), 7.00 (s, 3H), 6.62 (s, 1H),
5.37 (d, J = 7.4 Hz, 1H), 3.83 (d, J = 7.3 Hz, 1H), 3.79 (s, 3H),
2.76 (d, J = 16.4 Hz, 1H), 1.98 (d, J = 16.3 Hz, 1H), 1.03 (s, 3H),
0.88 (s, 3H). 13CNMR (101 MHz, DMSO) δ193.4, 159.3, 146.1,
35 136.9, 132.1, 130.1, 129.7, 128.7, 128.4, 127.5, 119.3, 114.8, 100 5.43 (d, J = 7.3 Hz, 1H), 3.86 (d, J = 7.2 Hz, 1H), 2.78 (d, J =
104.9, 68.0, 55.8, 47.2, 26.4, 25.9. HRMS (ESI-TOF) Calcd for
16.4 Hz, 1H), 2.36 (s, 3H), 2.00 (d, J = 16.4 Hz, 1H), 1.03 (s, 3H),
0.88 (s, 3H). 13CNMR (101 MHz, DMSO) δ 193.4, 146.4, 138.6,
135.1, 134.6, 134.1, 133.4, 130.5, 130.3, 128.2, 128.0, 127.3,
126.9, 119.5, 106.1, 89.4, 68.0, 47.2, 26.4, 25.8, 21.2, 15.9.
105 HRMS (ESI-TOF) Calcd for C23H23ClNO2+ ([M+H]+) 380.1417.
Found 380.1419.
C23H24NO3+ ([M+H]+)362.1756. Found 362.1758.
7-hydroxy-6,6-dimethyl-1,2-diphenyl-6,7-dihydro-1H-
indol-4(5H)-one(3e): yellow solid (113 mg, 68%). m. p.: 162ꢀ
40 163 ºC. IR (neat, ν, cmꢀ1): 3298, 2972, 2956, 2887, 1716, 1698,
1684, 1576, 737, 665 cmꢀ1. 1HNMR (400 MHz, DMSO) δ 7.45 (s,
4H), 7.20 (d, J = 6.5 Hz, 4H), 7.09 (d, J = 6.6 Hz, 2H), 6.64 (s,
1H), 5.43 (d, J = 7.3 Hz, 1H), 3.85 (d, J = 7.1 Hz, 1H), 2.77 (d, J
= 16.4 Hz, 1H), 1.99 (d, J = 16.3 Hz, 1H), 1.03 (s, 3H), 0.88 (s,
7-hydroxy-2-(4-methoxyphenyl)-6,6-dimethyl-1-(p-tolyl)-
6,7-dihydro-1H-indol-4(5H)-one(3k): yellow solid (124 mg,
66%). m. p.: 198ꢀ200 ºC. IR (neat, ν, cmꢀ1): 3414, 2969, 1634,
45 3H). 13CNMR (101 MHz, DMSO) δ 193.4, 145.9, 137.4, 136.8, 110 1613, 1560, 732, 691, 675 cmꢀ1. HNMR (400 MHz, DMSO) δ
1
132.0, 129.7, 128.9, 128.7, 128.5, 128.5, 127.6, 119.5, 105.3,
7.25 (s, 3H), 7.04 (d, J = 8.5 Hz, 3H), 6.79 (d, J = 8.5 Hz, 2H),
6.53 (s, 1H), 5.36 (d, J = 7.3 Hz, 1H), 3.83 (d, J = 7.2 Hz, 1H),
3.69 (s, 3H), 2.77 (d, J = 16.4 Hz, 1H), 2.35 (s, 3H), 1.97 (d, J =
16.0 Hz, 1H), 1.02 (s, 3H), 0.87 (s, 3H). 13CNMR (101 MHz,
115 DMSO) δ 193.4, 158.8, 145.5, 138.3, 136.7, 135.0, 130.2, 129.9,
+
68.1, 47.2, 26.4, 25.9. HRMS (ESI-TOF) Calcd for C22H22NO2
([M+H]+) 332.1651. Found 332.1658.
7-hydroxy-6,6-dimethyl-1-(4-methylbenzyl)-2-phenyl-6,7-
128.3, 124.5, 119.3, 114.2, 104.3, 68.1, 55.5, 47.2, 26.4, 25.9,
50 dihydro-1H-indol-4(5H)-one(3f): yellow solid (131 mg, 73%).
+
21.2. HRMS (ESI-TOF) Calcd for C24H26NO3 ([M+H]+)
m. p.: 163ꢀ164 ºC. IR (neat, ν, cmꢀ1): 2957, 2921, 2869, 1644,
376.1913. Found 376.1914.
1
1607, 1561, 760, 718, 677 cmꢀ1. HNMR (400 MHz, DMSO) δ
7.34 (dt, J = 10.7, 6.9 Hz, 5H), 7.10 (d, J = 7.8 Hz, 2H), 6.78 (d, J
= 7.9 Hz, 2H), 6.46 (s, 1H), 5.56 (d, J = 7.2 Hz, 1H), 5.35 (d, J =
7-hydroxy-6,6-dimethyl-1,2-di-p-tolyl-6,7-dihydro-1H-
55 17.1 Hz, 1H), 5.24 (d, J = 17.1 Hz, 1H), 4.07 (d, J = 7.0 Hz, 1H), 120 indol-4(5H)-one(3l): yellow solid (124 mg, 69%). m. p.: 180ꢀ182
2.70 (d, J = 16.2 Hz, 1H), 2.24 (s, 3H), 2.04 – 1.94 (m, 1H), 1.03
(s, 3H), 0.84 (s, 3H). 13CNMR (101 MHz, DMSO) δ 193.0, 144.8,
137.0, 136.7, 135.5, 132.2, 129.6, 129.1, 129.1, 128.3, 125.8,
ºC. IR (neat, ν, cmꢀ1): 3372, 2958, 1649, 1600, 1555, 763, 637
cmꢀ1. 1HNMR (400 MHz, DMSO) δ 7.25 (s, 3H), 7.01 (d, J = 2.6
Hz, 5H), 6.58 (s, 1H), 5.38 (s, 1H), 3.84 (s, 1H), 2.77 (d, J = 16.4
Hz, 1H), 2.35 (s, 3H), 2.22 (s, 3H), 1.98 (d, J = 16.4 Hz, 1H),
119.3, 105.0, 68.3, 47.6, 47.4, 26.3, 26.0, 21.1. HRMS (ESI-
+
60 TOF) Calcd for C24H26NO2 ([M+H]+) 360.1964. Found 125 1.03 (s, 3H), 0.87 (s, 3H). 13CNMR (101 MHz, DMSO) δ 193.4,
360.1967.
145.8, 138.3, 136.9, 134.9, 130.2, 129.3, 129.3, 128.4, 128.2,
119.4, 104.71, 68.1, 47.2, 26.4, 25.9, 21.1, 21.1. HRMS (ESI-
+
TOF) Calcd for C24H26NO2 ([M+H]+) 360.1964. Found
7-hydroxy-6,6-dimethyl-1-(naphthalen-2-yl)-2-phenyl-6,7-
360.1960.
dihydro-1H-indol-4(5H)-one(3g): yellow solid (132 mg, 69%).
m. p.: 101ꢀ102 ºC. IR (neat, ν, cmꢀ1): 2955, 2922, 2863, 1644,
1
65 1599, 1556, 752, 696, 660 cmꢀ1. HNMR (400 MHz, DMSO) δ
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