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CH2); 13C NMR (150 MHz, DMSO): d 179.5, 155.1, 136.9, 136.4,
128.3, 127.8, 126.4, 121.6, 119.4, 119.0, 115.5, 114.2, 110.0,
109.9, 107.2, 91.7, 74.2, 63.2, 58.8, 56.4, 42.9, 38.3, 34.2, 32.9,
29.2, 27.3, 24.8, 19.7.
5-Bromo-20-(1-methyl-1H-indol-3-yl)-10-nitro-10,20,4a0,50,60,70,
80,8a0,90,9a00-decahydrospiro[indoline-3,30-pyrrolo[1,2-a]indol]-
2-one (4g). Yellow solid; 94% yield; mp 223–225 ꢀC; IR (KBr) 739,
816, 1186, 1331, 1477, 1545, 1616, 1717, 2363, 2930, 3395, 3426,
3624 cmꢂ1; HRMS (EI) calcd for C27H27NaBrN4O3 [M + Na]+
557.1159, found 557.1157. 1H NMR (600 MHz, DMSO-D6):
d 10.30 (s, 1H, NH), 8.37 (s, 1H, ArH), 7.69 (d, J ¼ 7.2 Hz, 1H,
ArH), 7.24 (d, J ¼ 7.2 Hz, 3H, ArH), 7.05 (t, J ¼ 13.2 Hz, 1H, ArH),
6.94 (d, J ¼ 6.6 Hz, 1H, ArH), 6.51 (d, J ¼ 7.8 Hz, 1H, ArH), 6.38 (t,
J ¼ 20.4 Hz, 1H, CH), 4.93 (d, J ¼ 10.8 Hz, 1H, CH), 4.68 (d, J ¼
6.6 Hz, 1H, CH), 3.92 (s, 1H, CH), 3.65 (s, 3H, CH3), 2.16 (d, J ¼
4.2 Hz, 1H, CH), 1.83 (d, J ¼ 4.8 Hz, 1H, CH2), 1.54 (d, J ¼ 6.0 Hz,
3H, CH2), 1.25–1.16 (m, 2H, CH2), 1.10–0.98 (m, 3H, CH2), 0.56
(d, J ¼ 13.2 Hz, 1H, CH2); 13C NMR (150 MHz, DMSO): d 179.1,
142.9, 136.5, 132.6, 130.4, 128.1, 127.8, 127.7, 121.7, 119.4,
119.0, 113.7, 111.6, 110.0, 106.8, 91.0, 74.0, 63.4, 58.8, 43.2, 38.3,
34.2, 32.9, 29.3, 27.2, 24.8, 19.6.
5-Fluoro-20-(1-methyl-1H-indol-3-yl)-10-nitro-10,20,4a0,50,60,70,
80,8a0,90,9a0-decahydrospiro[indoline-3,30-pyrrolo[1,2-a]indol]-2-
one (4d). Yellow solid; 95% yield; mp 243–245 ꢀC; IR (KBr) 743,
820, 1177, 1329, 1375, 1489, 1547, 1720, 2938, 3410, 3424 cmꢂ1
;
HRMS (EI) calcd for C27H27NaFN4O3 [M + Na]+ 497.1959, found
1
497.1957. H NMR (600 MHz, DMSO-D6): d 10.21 (s, 1H, NH),
8.09 (d, J ¼ 7.8 Hz, 1H, ArH), 7.74 (d, J ¼ 7.8 Hz, 1H, ArH), 7.24
(d, J ¼ 9.0 Hz, 2H, ArH), 7.04 (d, J ¼ 7.2 Hz, 1H, ArH), 6.96–6.92
(m, 2H, ArH), 6.55 (s, 1H, ArH), 6.40 (t, J ¼ 20.4 Hz, 1H, CH), 4.91
(d, J ¼ 11.4 Hz, 1H, CH), 4.71 (d, J ¼ 6.6 Hz, 1H, CH), 3.93 (s, 1H,
CH), 3.64 (s, 3H, NCH3), 2.16 (d, J ¼ 3.6 Hz, 1H, CH), 1.81 (d, J ¼
4.8 Hz, 1H, CH2), 1.55 (s, 3H, CH3), 1.27–1.19 (m, 2H, CH2),
1.09–0.99 (m, 3H, CH2), 0.55 (d, J ¼ 12.6 Hz, 1H, CH2); 13C NMR
(150 MHz, DMSO): d 179.5, 159.0, 157.5, 140.0, 136.4, 128.2,
127.9, 121.7, 119.3, 119.1, 116.3, 116.2, 115.5, 110.4, 110.4,
106.9, 91.3, 74.1, 63.3, 58.8, 43.2, 38.3, 34.2, 32.9, 29.2, 27.3,
24.8, 19.6.
5-Methoxy-10-methyl-20-(1-methyl-1H-indol-3-yl)-10-nitro-
10,20,4a0,50,60,70,80,8a0,90,9a0-decahydrospiro[indoline-3,30-pyrrolo-
[1,2-a]indol]-2-one (4h). Yellow solid; 87% yield; mp 215–217 ꢀC;
IR (KBr) 741, 1042, 1120, 1489, 1543, 1732, 2365, 2930,
3304 cmꢂ1; HRMS (EI) calcd for C29H33N4O4 [M + H]+ 501.2496,
6-Chloro-20-(1-methyl-1H-indol-3-yl)-10-nitro-10,20,4a0,50,60,70,
80,8a0,90,9a0-decahydrospiro[indoline-3,30-pyrrolo[1,2-a]indol]-2-
one (4e). Yellow solid; 95% yield; mp 182–184 ꢀC; IR (KBr) 739,
1072, 1126, 1333, 1449, 1543, 1609, 1707, 2936, 3248, 3416,
3503, 3624 cmꢂ1; HRMS (EI) calcd for C27H27NaClN4O3 [M +
1
found 501.2499. H NMR (500 MHz, DMSO-D6): d 10.30 (s, 1H,
NH), 7.84 (d, J ¼ 7.5 Hz, 1H, ArH), 7.53 (s, 1H, ArH), 7.39 (d, J ¼
8.5 Hz, 1H, ArH), 7.17–7.11 (m, 1H, ArH), 7.09 (d, J ¼ 7.5 Hz, 2H,
ArH), 6.89–6.86 (m, 1H, ArH), 6.74 (d, J ¼ 8.5 Hz, 1H, ArH), 4.52
(d, J ¼ 11.0 Hz, 1H, CH), 4.26–4.25 (m, 1H, CH), 3.80 (s, 3H,
NCH3), 3.78 (s, 3H, OCH3), 3.17 (d, J ¼ 3.5 Hz, 1H, CH), 2.09–
2.06 (m, 1H, CH2), 1.89 (s, 3H, CH3), 1.76–1.75 (m, 1H, CH2),
1.56–1.52 (m, 2H, CH2), 1.46–1.36 (m, 3H, CH2), 1.19–1.12 (m,
2H, CH2), 1.03–0.96 (m, 2H, CH2); 13C NMR (125 MHz, DMSO):
d 177.5, 154.4, 136.8, 136.3, 130.0, 128.6, 125.4, 121.5, 120.1,
119.3, 115.1, 114.3, 110.6, 110.1, 106.8, 101.4, 74.7, 66.7, 58.0,
56.1, 48.6, 40.4, 37.4, 33.0, 27.8, 27.6, 24.7, 20.2, 19.7.
1
Na]+ 513.1664, found 513.1668. H NMR (600 MHz, DMSO-D6):
d 10.36 (s, 1H, NH), 8.08 (d, J ¼ 7.8 Hz, 1H, CH2), 7.66 (d, J ¼
7.2 Hz, 1H, CH2), 7.25 (d, J ¼ 12.0 Hz, 2H, CH2), 7.06 (t, J ¼
14.4 Hz, 1H, CH2), 6.98 (d, J ¼ 7.2 Hz, 1H, CH2), 6.93 (t,
J ¼ 14.4 Hz, 1H, CH2), 6.59 (s, 1H, CH2), 6.38 (t, J ¼ 21.0 Hz, 1H,
CH), 4.88 (d, J ¼ 11.4 Hz, 1H, CH), 4.69 (d, J ¼ 7.2 Hz, 1H, CH),
3.87 (s, 1H, CH), 3.65 (s, 1H, NCH3), 2.16 (d, J ¼ 5.4 Hz, 1H, CH),
1.80–1.76 (m, 1H, CH2), 1.57–1.52 (m, 3H, CH2), 1.28–1.15 (m,
2H, CH2), 1.09–0.94 (m, 3H, CH2), 0.57–0.54 (m, 1H, CH2); 13C
NMR (150 MHz, DMSO): d 179.4, 145.1, 136.4, 134.4, 128.9,
128.1, 128.0, 124.2, 121.7, 121.3, 119.2, 119.1, 110.0, 110.0,
106.7, 91.3, 73.5, 63.3, 59.0, 49.1, 38.3, 34.2, 32.9, 29.3, 27.2,
24.7, 19.6.
6-Bromo-20-(1-methyl-1H-indol-3-yl)-10-nitro-10,20,4a0,50,60,70,
80,8a0,90,9a0-decahydrospiro[indoline-3,30-pyrrolo[1,2-a]indol]-2-
one (4f). Yellow solid; 96% yield; mp 223–225 ꢀC; IR (KBr) 739,
1067, 1128, 1333, 1447, 1481, 1543, 1607, 1107, 2934, 3258,
3416, 3501, 3622 cmꢂ1; HRMS (EI) calcd for C27H27NaBrN4O3 [M
+ Na]+ 557.1159, found 557.1164. 1H NMR (600 MHz, DMSO-D6):
d 10.30 (s, 1H, NH), 8.01 (d, J ¼ 6.0 Hz, 1H, ArH), 7.66 (d, J ¼
7.8 Hz, 1H, ArH), 7.25 (t, J ¼ 19.2 Hz, 2H, ArH), 7.12 (t, J ¼
8.4 Hz, 1H, ArH), 7.05 (t, J ¼ 15.0 Hz, 1H, ArH), 6.93 (t,
J ¼ 14.4 Hz, 1H, ArH), 6.72 (d, J ¼ 1.8 Hz, 1H, ArH), 6.39–6.35 (m,
1H, CH), 4.93 (d, J ¼ 10.8 Hz, 1H, CH), 4.68 (d, J ¼ 6.6 Hz, 1H,
CH), 3.92 (s, 1H, CH), 3.65 (s, 3H, CH3), 3.19 (d, J ¼ 4.8 Hz, 1H,
CH), 2.16–2.14 (m, 1H, CH2), 1.79–1.76 (m, 1H, CH2), 1.57–1.52
(m, 3H, CH2), 1.25–1.16 (m, 2H, CH2), 1.10–0.98 (m, 3H, CH2);
13C NMR (150 MHz, DMSO): d 179.3, 145.3, 136.4, 129.2, 128.1,
128.0, 124.6, 124.2, 122.9, 121.7, 119.2, 112.7, 110.0, 106.7, 91.4,
73.6, 63.3, 59.0, 49.1, 43.1, 38.3, 34.2, 32.9, 29.3, 27.2, 24.7, 19.6.
5-Fluoro-10-methyl-20-(1-methyl-1H-indol-3-yl)-10-nitro-10,20,
4a0,50,60,70,80,8a0,90,9a0-decahydrospiro[indoline-3,30-pyrrolo[1,2-
ꢀ
a]indol]-2-one (4i). Yellow solid; 92% yield; mp 170–172 C; IR
(KBr) 741, 818, 1182, 1333, 1487, 1537, 1717, 2930, 3393,
3426 cmꢂ1; HRMS (EI) calcd for C28H28NaFN4O3 [M + Na]+
511.2116, found 511.2120. 1H NMR (500 MHz, DMSO-D6):
d 10.31 (s, 1H, NH), 7.76–7.73 (m, 1H, ArH), 7.67 (d, J ¼ 8.0 Hz,
1H, ArH), 7.27 (d, J ¼ 8.0 Hz, 1H, ArH), 7.11 (s, 1H, ArH), 7.08–
7.01 (m, 1H, ArH), 6.99–6.91 (m, 1H, ArH), 6.90–6.88 (m, 1H,
ArH), 6.60–6.57 (m, 1H, ArH), 4.44–4.41 (m, 1H, CH), 3.74 (d, J ¼
3.5 Hz, 1H, CH), 3.69 (s, 3H, NCH3), 2.13–2.09 (m, 1H, CH), 2.08
(s, 3H, CH3), 1.73–1.69 (m, 1H, CH2), 1.59–1.55 (m, 1H, CH2),
1.52–1.50 (m, 2H, CH2), 1.27–1.24 (m, 1H, CH2), 1.19–1.18 (m,
1H, CH2), 1.07–1.02 (m, 2H, CH2), 1.00–0.91 (m, 1H, CH2), 0.55–
0.52 (m, 1H, CH2); 13C NMR (125 MHz, DMSO): d 180.3, 159.1,
157.2, 139.6, 136.0, 129.2, 128.9, 128.4, 121.7, 119.4, 118.7,
116.4, 114.2, 110.4, 110.4, 104.9, 99.8, 74.4, 73.9, 58.1, 50.3, 38.9,
36.3, 33.0, 28.7, 27.5, 25.9, 24.5, 19.4.
5-Chloro-10-methyl-20-(1-methyl-1H-indol-3-yl)-10-nitro-10,20,
4a0,50,60,70,80,8a0,90,9a0-decahydrospiro[indoline-3,30-pyrrolo[1,2-
ꢀ
a]indol]-2-one (4j). Yellow solid; 92% yield; mp 183–185 C; IR
(KBr) 743, 820, 1194, 1474, 1543, 1614, 1738, 2859, 2928,
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RSC Adv., 2018, 8, 5702–5713 | 5707