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119.8, 119.6, 110.4, 106.7, 29.6, 8.1; HRMS (ESI-MS) calcd for 8.0 Hz), 7.46 (1H, d, J ¼ 8.0 Hz), 7.20 (1H, t, J ¼ 8.0 Hz), 7.09 (1H,
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18H15N3O (M + H) 290.1293 found 290.1291.
3-(1,3-Dimethyl-1H-indol-2-yl)-4a,10a-dihydro-3H-benzo[g] 147.7, 147.4, 135.6, 134.9, 131.9, 128.3, 127.9, 126.9, 122.7,
t, J ¼ 8.0 Hz), 6.69 (1H, s); 13C NMR (100 MHz, DMSO-d6) d 160.3,
quinazolin-4-one (3j). Compound was obtained as light yellow 121.9, 120.9, 120.2, 112.1, 98.1; HRMS (ESI-MS) calcd for
solid (137 mg, 60%); m.p. ¼ 164 ꢁC; IR (KBr) 3310, 2894, 1682,
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16H11N3O (M + H) 262.0980, found 262.0981.
3-(3-Iodo-1H-indol-2-yl)-3H-quinazolin-4-one
1249, 942, 756 cmꢀ1; 1H NMR (400 MHz, DMSO-d6) d 8.99 (1H,
(5aa).
s), 8.39 (1H, s), 8.31 (1H, s), 8.27 (1H, d, J ¼ 8.4 Hz), 8.18 (1H, Compound was obtained as bright yellow solid; (144 mg, 55%);
d, J ¼ 8.4 Hz), 7.73 (1H, t, J ¼ 7.6 Hz), 7.66–7.62 (2H, m), 7.51 m.p. ¼ 205 ꢁC; IR (KBr) 3342, 3063, 1682, 1254, 904, 767 cmꢀ1
;
(1H, d, J ¼ 8.4 Hz), 7.28 (1H, t, J ¼ 7.6 Hz), 7.14 (1H, t, J ¼ 7.2 1H NMR (400 MHz, DMSO-d6) d 12.34 (1H, s), 8.42 (1H, s), 8.26
Hz), 3.56 (3H, s), 2.16 (3H, s); 13C NMR (100 MHz, DMSO-d6) d (1H, d, J ¼ 8.0 Hz), 7.96 (1H, t, J ¼ 8.0 Hz), 7.81 (1H, d, J ¼ 8.0
161.4, 146.9, 143.4, 136.8, 135.3, 131.9, 129.9, 129.6, 128.9, Hz), 7.67 (1H, t, J ¼ 7.2 Hz), 7.48 (1H, d, J ¼ 8.0 Hz), 7.39 (1H, d, J
128.5, 127.4, 126.5, 125.9, 123.1, 120.8, 119.8, 119.6, 110.4, ¼ 7.6 Hz), 7.30 (1H, t, J ¼ 7.2 Hz), 7.21 (1H, t, J ¼ 7.6 Hz); 13C
106.7, 29.6, 8.2; HRMS (ESI-MS) calcd for C22H17N3O (M + H) NMR (100 MHz, DMSO-d6) d 160.2, 147.9, 147.8, 136.0, 135.3,
340.1450, found 340.1450.
133.2, 129.3, 128.6, 128.2, 127.1, 124.2, 121.8, 121.2, 121.1,
112.8, 58.8; HRMS (ESI-MS) calcd for C16H10IN3O (M + H)
3-(1-Benzyl-3-methyl-1H-indol-2-yl)-4a,8a-dihydro-3H-quina-
zolin-4-one (3k). Compound was obtained as light grayish solid 387.9947, found 387.9946.
(169 mg, 68%); m.p. ¼ 106 ꢁC; IR (KBr) 3364, 3024, 2909, 1687,
3-(5-Methoxy-1H-indol-2-yl)-3H-quinazolin-4-one (5b)
3-(3-Iodo-5-methoxy-1H-indol-2-yl)-3H-quinazolin-4-one (5bb).
1610, 1249, 920, 739 cmꢀ1; 1H NMR (500 MHz, DMSO-d6) d 8.23
(1H, d, J ¼ 8.0 Hz), 8.14 (1H, s), 7.92 (1H, t, J ¼ 7.5 Hz), 7.74 (1H, Compounds were obtained as bright yellow solid mixture with
d, J ¼ 8.0 Hz), 7.68 (1H, d, J ¼ 8.0 Hz), 7.64 (1H, t, J ¼ 7.5 Hz), ratio of (5b : 5bb ¼ 1 : 0.41); (overall 108 mg, 45%); IR (KBr)
7.45 (1H, d, J ¼ 8.0 Hz), 7.24 (1H, t, J ¼ 7.5 Hz), 7.18–7.14 (4H, 3358, 3260, 2991, 2926, 1682, 1654, 1254, 1210, 767, 690 cmꢀ1
;
m), 6.96–6.94 (2H, m), 5.43 (1H, d, J ¼ 17 Hz), 5.05 (1H, d, J ¼ 17 1H NMR (400 MHz, DMSO-d6) d 12.20 (0.396H, s), 11.62 (1.00H,
Hz), 2.15 (3H, m). 13C NMR (125 MHz, DMSO-d6) d 160.8, 147.9, s), 8.46 (1.040H, s), 8.38 (0.443H, s), 8.25–8.23 (1.428H, m), 7.97–
147.7, 137.9, 135.7, 135.1, 129.2, 128.9, 128.4, 128.0, 127.7, 7.89 (1.433H, m), 7.82–7.76 (1.390H, m), 7.68–7.61 (1.392H, m),
127.1, 126.9, 126.7, 123.5, 121.9, 120.1, 119.9, 110.9, 107.9, 46.6, 7.39–7.32 (1.459H, m), 7.102 (1.063H, s), 6.94–6.92 (0.446H, m),
8.2; HRMS (ESI-MS) calcd for C24H19N3O (M + H) 366.1606, 6.84–6.82 (1.387H, m), 6.59 (0.978H, s), 3.81 (1.184H, s), 3.76
found 366.1606.
(2.961H, s); 13C NMR (100 MHz, DMSO-d6) d 160.3, 155.0, 154.2,
3-(1-Benzyl-3-methyl-1H-indol-2-yl)-4a,10a-dihydro-3H-benzo 147.7, 147.4, 135.6, 132.1, 129.9, 128.4, 127.9, 127.4, 126.9,
[g]quinazolin-4-one (3l). Compound was obtained as light yellow 121.9, 113.0, 112.9, 102.5, 97.9, 55.8; HRMS (ESI-MS) calcd for
solid (130 mg, 46%); m.p. ¼ 130 ꢁC; IR (KBr) 3052, 2920, 1687, 5b C17H13N3O2 (M + H) 292.1086, found 292.1079; for 5bb
1600, 1265, 898, 750 cmꢀ1; 1H NMR (400 MHz, DMSO-d6) d 8.96
(1H, s), 8.31 (1H, s), 8.27 (1H, d, J ¼ 8.4 Hz), 8.16 (1H, d, J ¼ 8.4
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17H12IN3O2 (M + H) 418.0052, found 418.0051.
3-(5-Bromo-1H-indol-2-yl)-3H-quinazolin-4-one
(5c).
Hz), 8.08 (1H, s), 7.72 (1H, t, J ¼ 7.2 Hz), 7.68–7.62 (2H, m), 7.45 Compound was obtained as bright yellow solid (70 mg, 30%);
(1H, d, J ¼ 8.0 Hz), 7.30 (1H, d, J ¼ 6.4 Hz), 7.24 (1H, t, J ¼ 7.6 m.p. ¼ 188 ꢁC; IR (KBr) 3221, 2926, 1682, 1654, 904, 772 cmꢀ1
;
Hz), 7.17–7.14 (3H, m), 6.99–6.96 (2H, m), 5.45 (1H, d, J ¼ 16.8 1H NMR (400 MHz, DMSO-d6) d 12.03 (1H, s), 8.48 (1H, s), 8.25
Hz), 5.09 (1H, d, J ¼ 16.8 Hz), 2.17 (3H, s); 13C NMR (100 MHz, (1H, d, J ¼ 8.0 Hz), 7.92 (1H, t, J ¼ 7.6 Hz), 7.81 (1H, s), 7.77 (1H,
DMSO-d6) d 161.3, 146.6, 143.2, 138.1, 136.7, 135.1, 131.9, 129.9, d, J ¼ 8.0 Hz), 7.64 (1H, t, J ¼ 7.6 Hz), 7.42 (1H, d, J ¼ 8.8 Hz),
129.5, 129.3, 129.1, 128.9, 128.4, 127.7, 127.6, 127.4, 126.9, 7.30 (1H, d, J ¼ 8.8 Hz), 6.69 (1H, s); 13C NMR (100 MHz, DMSO-
126.8, 125.8, 123.4, 120.7, 120.0, 119.8, 110.9, 107.9, 46.61, 8.2; d6) d 160.2, 147.7, 147.2, 135.7, 133.5, 133.2, 128.8, 128.4, 128.0,
HRMS (ESI-MS) calcd for C28H21N3O (M + H) 416.1763, found 126.9, 125.3, 123.2, 121.8, 114.2, 112.6, 97.7; HRMS (ESI-MS)
416.1764.
3-(1-Benzyl-3-methyl-1H-indol-2-yl)-3H-pyrimidin-4-one (3m). C16H10Br81N3O (M + H) 342.0065, found 342.0085.
3-(5-Bromo-3-iodo-1H-indol-2-yl)-3H-quinazolin-4-one
calcd for C16H10Br79N3O (M + H) 340.0085, found 340.0082;
Compound was obtained as yellow solid (132 mg, 62%); m.p. ¼
(5cc).
102 ꢁC; IR (KBr) 3079, 2915, 1731, 1698, 1282, 843, 739 cmꢀ1; 1H Compound was obtained as bright yellow solid (111 mg, 35%);
NMR (400 MHz, DMSO-d6) d 8.22 (1H, s), 7.99 (1H, d, J ¼ 6.8 Hz), m.p. ¼ 218 ꢁC; IR (KBr) 3407, 2932, 1675, 1601, 1455, 1008, 938
7.66 (1H, d, J ¼ 7.6 Hz), 7.48 (1H, d, J ¼ 8.0 Hz), 7.26–7.13 (5H, cmꢀ1; 1H NMR (500 MHz, DMSO-d6) d 12.59 (1H, s), 8.43 (1H, s),
m), 6.97–6.95 (2H, m), 6.59 (1H, dd, J ¼ 6.8 Hz, J ¼ 0.8 Hz), 5.43 8.26 (1H, dd, J ¼ 8.0 Hz, J ¼ 1.0 Hz), 7.99–7.95 (1H, m), 7.82 (1H,
(1H, d, J ¼ 16.4 Hz), 4.94 (1H, d, J ¼ 16.8 Hz), 2.11 (3H, s); 13C d, J ¼ 8.0 Hz), 7.68 (1H, t, J ¼ 8.0 Hz), 7.55 (1H, d, J ¼ 1.5 Hz),
NMR (100 MHz, DMSO-d6) d 160.5, 154.4, 153.3, 137.8, 135.2, 7.49 (1H, d, J ¼ 9.0 Hz), 7.43 (1H, dd, J ¼ 8.5 Hz, J ¼ 2.0 Hz); 13
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129.0, 128.8, 127.8, 126.9, 126.6, 123.6, 120.1, 119.9, 116.3, 110.8, NMR (100 MHz, DMSO-d6) d 160.1, 147.8, 147.5, 136.1, 134.5,
107.7, 46.6, 8.1; HRMS (ESI-MS) calcd for C20H17N3O (M + H) 134.1, 131.1, 128.7, 128.2, 127.1, 126.9, 123.2, 121.7, 115.0,
316.1450, found 316.1451.
113.6, 58.1; HRMS (ESI-MS) calcd for C16H9Br79IN3O (M + H)
3-(1H-indol-2-yl)-3H-quinazolin-4-one (5a). Compound was 465.9052, found 465.9049, C16H9Br81IN3O (M + H) 467.9031,
obtained as yellow solid (89 mg, 50%); m.p. ¼ 140 ꢁC; IR (KBr) found 467.9028.
3276, 2920, 1660, 1600, 1265, 1008, 734 cmꢀ1
;
1H NMR (400
3-(6-Bromo-1H-indol-2-yl)-3H-quinazolin-4-one (5d)
MHz, DMSO-d6) d 11.81 (1H, s), 8.49 (1H, s), 8.23 (1H, d, J ¼ 8.0
3-(6-Bromo-3-iodo-1H-indol-2-yl)-3H-quinazolin-4-one
Hz), 7.92–7.88 (1H, m), 7.77 (1H, d, J ¼ 8.0 Hz), 7.63 (2H, t, J ¼ Compounds were obtained as bright yellow solid mixture with
(5dd).
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RSC Adv., 2014, 4, 20136–20144 | 20141