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(s {weak}, 1H, –NH), 10.89 (s {weak}, 1H, –OH). 13C NMR (100
MHz, DMSO-d6): d 35.79, 100.68, 104.33, 107.50, 107.72, 115.93
(2C), 118.00, 119.49 (2C), 123.68 (2C), 123.89 (2C), 128.66,
131.57, 131.83 (2C), 133.91, 145.16, 147.27, 152.23 (2C), 164.70,
165.29. IR nmax (KBr): 3409, 3295, 3119, 3084, 3049, 2893, 1655,
1636, 1607, 1560, 1491, 1232, 1184, 1040, 933, 764 cmꢂ1. TOF-
MS: calcd for C25H17NO5Na [M + Na]+: 434.1004; found:
434.1001. Anal. calcd for C25H17NO5: C, 72.99; H, 4.16; N, 3.40;
found: C, 72.95; H, 4.16; N, 3.39.
3-((5-Bromo-1H-indol-3-yl)(phenyl)methyl)-4-hydroxy-6-methyl-
2H-pyran-2-one (4bc). Deep brown solid (0.246 g, 60%); mp 110–
112 ꢁC; [a]2D5 ¼ +35.3 (acetone, c 1.0); e.r. could not be evaluated at
this time. 1H NMR (400 MHz, DMSO-d6): d 2.15 (s, 3H, –CH3), 5.76
(s, 1H, –CH), 6.03 (s, 1H, –CH), 7.09 (d, J ¼ 2 Hz, 1H, ArH), 7.12–
7.15 (m, 2H, ArH), 7.23–7.24 (m, 4H, ArH), 7.32 (s, 1H, ArH), 7.34–
7.37 (m, 1H, ArH), 11.07 (s, 1H, –NH), 11.46 (s, 1H, –OH). 13C NMR
(100 MHz, DMSO-d6): d 19.28, 35.91, 101.55, 103.65, 110.84,
113.46, 114.64, 120.56, 123.10, 125.65, 125.90, 126.53, 127.70,
127.96, 128.06, 129.04, 134.62, 142.63, 163.75, 165.38, 166.32. IR
nmax (KBr): 3398, 3362, 3317, 3076, 3006, 2922, 2851, 1668, 1570,
1556, 1447, 1275, 1099, 1033, 987, 878, 702 cmꢂ1. TOF-MS: calcd
for C21H16BrNO3Na [M + Na]+: 432.0211; found: 432.0218. Anal.
calcd for C21H16BrNO3: C, 61.48; H, 3.93; N, 3.41; found: C, 61.46;
H, 3.95; N, 3.43.
2-((1H-Indol-3-yl)(phenyl)methyl)-3-hydroxy-5,5-dimethylcy-
clohex-2-enone (4ca). Brownish white solid (0.242 g, 70%); mp
164–168 ꢁC; [a]2D5 ¼ +22.7 (acetone, c 1.0); e.r. could not be
evaluated at this time. 1H NMR (400 MHz, DMSO-d6): d 1.01 (s,
6H, 2CH3), 2.28 (s, 4H, 2CH2), 5.83 (s, 1H, –CH), 6.86–6.92 (m,
2H, ArH), 7.02 (t, J ¼ 7.6, 7.2 Hz, 1H, ArH), 7.08 (d, J ¼ 4 Hz, 1H,
ArH), 7.17–7.22 (m, 5H, ArH), 7.34 (d, J ¼ 8 Hz, 1H, ArH), 10.37
(br s, 1H, –NH), 10.73 (s, 1H, –OH). 13C NMR (100 MHz, DMSO-
d6): d 28.42 (2C), 32.07, 35.42, 46.50, 49.38, 111.69, 116.39,
117.15, 118.41, 119.04, 120.96, 124.54, 125.32, 127.77, 127.94
(2C), 128.61 (2C), 136.43, 145.14, 165.41, 195.54. IR nmax (KBr):
3443, 3394, 3325, 3269, 3240, 3045, 2949, 2862, 1676, 1601,
1581, 1564, 1495, 1448, 1265, 1225, 1148, 1105, 1016, 863, 949,
741 cmꢂ1. TOF-MS: calcd for C23H23NO2Na [M + Na]+: 368.1626;
found: 368.1630. Anal. calcd for C23H23NO2: C, 79.97; H, 6.71; N,
4.05; found: C, 79.95; H, 6.69; N, 4.09.
3-((5-Bromo-1H-indol-3-yl)(phenyl)methyl)-4-hydroxy-2H-
chromen-2-one (4af). Brownish white solid (0.237 g, 53%); mp
138–140 ꢁC; [a]2D5 ¼ +12.8 (acetone, c 1.0); e.r. could not be
evaluated at this time. 1H NMR (400 MHz, DMSO-d6): d 6.09 (s,
1H, –CH), 7.15–7.19 (m, 2H, ArH), 7.23–7.29 (m, 5H, ArH), 7.35–
7.38 (m, 3H, ArH), 7.48 (d, J ¼ 1.6 Hz, 1H, ArH), 7.59–7.63 (m,
1H, ArH), 8.05 (dd, J ¼ 1.6, 0.8, 8.2 Hz, 1H, ArH), 11.17 (d, J ¼ 1.2
Hz, 1H, –NH), 11.75 (br s, 1H, –OH). 13C NMR (100 MHz, DMSO-
d6): d 37.18, 108.63, 111.45, 114.00, 114.38, 116.67, 121.16,
123.37, 123.69, 123.99, 124.29, 126.23, 126.68, 128.24 (2C),
128.46 (2C), 129.59, 132.41, 135.08, 142.80, 152.65, 160.82,
162.15. IR nmax (KBr): 3398, 3265, 3242, 3074, 3022, 2895, 2860,
1687, 1616, 1566, 1489, 1452, 1415, 1326, 1248, 1169, 1105,
1041, 939, 887, 758 cmꢂ1. TOF-MS: calcd for C24H16BrNO3Na [M
+ Na]+: 468.0211; found: 468.0218. Anal. calcd for C24H16BrNO3:
C, 64.59; H, 3.61; N, 3.14; found: C, 64.63; H, 3.60; N, 3.17.
3-((5-Fluoro-1H-indol-3-yl)(phenyl)methyl)-4-hydroxy-2H-
chromen-2-one (4ah). Reddish white solid (0.235 g, 61%); mp
178–179 ꢁC; [a]2D5 ¼ +23.2 (acetone, c 1.0); e.r. could not be
evaluated at this time. 1H NMR (400 MHz, DMSO-d6): d 6.06 (s,
1H, –CH), 6.88–6.92 (m, 1H, ArH), 7.01 (d, J ¼ 10 Hz, 1H, ArH),
7.15–7.18 (m, 1H, ArH), 7.23–7.29 (m, 5H, ArH), 7.34–7.38 (m,
3H, ArH), 7.61 (t, J ¼ 8, 7.6 Hz, 1H, ArH), 8.03 (d, J ¼ 7.6 Hz, 1H,
ArH), 11.06 (s, 1H, –NH), 11.80 (br s, 1H, –OH). 13C NMR
(100 MHz, DMSO-d6): d 37.34, 103.42, 103.65, 108.62, 109.22,
109.47, 112.85, 112.95, 114.79, 116.67, 123.95, 124.30, 126.21,
127.03, 127.86, 127.95, 128.24, 128.48, 132.41, 133.05, 142.77,
152.63, 160.84, 162.17. IR nmax (KBr): 3480, 3328, 3278, 3107,
2-((1H-Indol-3-yl)(p-tolyl)methyl)-3-hydroxy-5,5-dimethylcy-
clohex-2-enone (4cb). Reddish white solid (0.223 g, 62%); mp
25
ꢁ
88–92 C; [a]D ¼ +23.8 (acetone, c 1.0); e.r. could not be eval-
uated at this time. 1H NMR (400 MHz, DMSO-d6): d 1.00 (s, 6H,
2CH3), 2.16 (d, J ¼ 8 Hz, 2H, –CH2), 2.21 (s, 3H, CH3), 2.37–2.39
(m, 2H, –CH2), 5.78 (s, 1H, –CH), 6.85–6.90 (m, 2H, ArH), 6.96–
7.07 (m, 5H, ArH), 7.19 (d, J ¼ 7.6 Hz, 1H, ArH), 7.33 (d, J ¼ 8 Hz,
1H, ArH), 10.30 (s, 1H, –NH), 10.71 (s, 1H, –OH). 13C NMR (100
MHz, DMSO-d6): d 20.60, 27.97, 31.63 (2C), 34.62, 43.32, 50.45,
111.23, 116.07, 116.86, 117.94, 118.64, 120.49, 124.03, 127.49,
127.95 (2C), 128.11 (2C), 133.60, 136.01, 141.62, 170.29, 196.05.
IR nmax (KBr): 3406, 3396, 3317, 3108, 2951, 2920, 2856, 1650,
1602, 1591, 1573, 1454, 1255, 1225, 1094, 1012, 742 cmꢂ1. TOF-
MS: calcd for C24H25NO2Na [M + Na]+: 382.1783; found:
382.1788. Anal. calcd for C24H25NO2: C, 80.19; H, 7.01; N, 3.90;
found: C, 80.21; H, 6.99; N, 3.91.
1686, 1614, 1564, 1494, 1219, 1161, 1061, 897, 847, 760 cmꢂ1
.
TOF-MS: calcd for C24H16FNO3Na [M + Na]+: 408.1012; found:
408.1015. Anal. calcd for C24H16FNO3: C, 74.80; H, 4.18; N, 3.63;
found: C, 74.88; H, 4.15; N, 3.61.
3-((4-Chlorophenyl)(1H-indol-3-yl)methyl)-4-hydroxy-6-methyl-
2H-pyran-2-one (4bb). Brown solid (0.209 g, 57%); mp 107–109
ꢁC; [a]2D5 ¼ +23.6 (acetone, c 1.0); e.r. could not be evaluated at
this time. 1H NMR (400 MHz, DMSO-d6): d 2.15 (s, 3H, –CH3),
5.78 (s, 1H, –CH), 6.02 (s, 1H, –CH), 6.90 (t, J ¼ 7.6 Hz, 1H,
ArH), 7.03–7.06 (m, 2H, ArH), 7.22–7.27 (m, 5H, ArH), 7.35 (d,
J ¼ 8 Hz, 1H, ArH), 10.86 (s, 1H, –NH), 11.51 (br s, 1H, –OH).
13C NMR (100 MHz, DMSO-d6): d 19.35, 35.63, 100.02, 103.78,
111.49, 114.23, 118.38, 120.86 (2C), 124.13, 127.11, 127.57
(2C), 130.06 (2C), 130.10, 136.03, 142.26, 161.03, 163.90,
165.52. IR nmax (KBr): 3402, 3261, 3042, 2945, 2920, 1670,
2-((4-Fluorophenyl)(1H-indol-3-yl)methyl)-3-hydroxy-5,5-
dimethylcyclohex-2-enone (4cc). Reddish brown white solid
(0.244 g, 67%); mp 105–107 ꢁC; [a]2D5 ¼ +35.1 (acetone, c 1.0); e.r.
could not be evaluated at this time. 1H NMR (400 MHz, DMSO-
d6): d 1.00 (s, 6H, 2CH3), 2.17 (br s, 2H, –CH2), 2.40 (br s, 2H,
–CH2), 5.80 (s, 1H, –CH), 6.88 (dd, J ¼ 7.6, 8 Hz, 2H, ArH), 6.96–
7.04 (m, 3H, ArH), 7.15–7.20 (m, 3H, ArH), 7.34 (d, J ¼ 8 Hz, 1H,
ArH), 10.44 (s, 1H, –NH), 10.75 (s, 1H, –OH). 13C NMR (100 MHz,
DMSO-d6): d 28.39 (2C), 32.06, 34.84, 43.65, 50.84, 111.73,
1634, 1576, 1489, 1444, 1404, 1279, 1094, 968, 831, 742 cmꢂ1
.
TOF-MS: calcd for C21H16ClNO3Na [M + Na]+: 388.0716; found:
388.0721. Anal. calcd for C21H16ClNO3: C, 68.95; H, 4.41; N,
3.83; found: C, 68.97; H, 4.39; N, 3.85.
This journal is © The Royal Society of Chemistry 2014
RSC Adv., 2014, 4, 7380–7388 | 7385