Molecules 2009, 14
3960
(CH), 78.3 (CH2), 36.6 (CH); MS (EI) m/z (relative intensity): 311 (19) [M]+, 264 (29), 247 (33), 219
(100), 204 (39), 130 (57); HRMS-EI: m/z [M]+ calcd for C16H13N3O4: 311.0906; found: 311.0901.
1
3-(1-Nitromethylpentyl)-1H-indole (2l): H-NMR (400 MHz, CDCl3): δ 8.06 (brs, 1H), 7.61 (d,
J = 7.8 Hz, 1H), 7.34 (d, J = 8.1 Hz, 1H), 7.23-7.18 (m, 1H), 7.15-7.11 (m, 1H), 6.98 (d, J = 2.0 Hz,
1H), 4.59 (m, 2H), 3.86 (m, 1H), 1.89 (m, 1H), 1.52 (m, 2H), 0.89 (d, J = 6.0 Hz, 3H), 0.87 (d,
J = 6.0 Hz, 3H); 13C-NMR (100 MHz, CDCl3): δ 136.5 (C), 126.1 (C), 122.4 (CH), 122.1 (CH), 119.7
(CH), 118.7 (CH), 114.1 (C), 111.5 (CH), 81.0 (CH2), 41.4 (CH), 34.4 (CH2), 25.4 (CH2), 23.3 (CH2),
21.5 (CH3); MS (EI) m/z (relative intensity): 246 (19) [M]+, 178 (11), 157 (30), 144 (18), 143 (61), 130
(100), 115 (22), 77 (10); HRMS-EI: m/z [M]+ calcd for C14H18O2N2: 246.1368; found: 246.1370.
1
3-(3-Methyl-1-nitromethylbutyl)-1H-indole (2m): H-NMR (400 MHz, CDCl3): δ 8.07 (brs, 1H), 7.62
(d, J = 7.8 Hz, 1H), 7.33 (d, J = 8.1 Hz, 1H), 7.20 (m, 1H), 7.13 (m, 1H), 6.99 (d, J = 2.2 Hz, 1H), 4.59
(m, 2H), 3.87 (m, 1H), 1.89 (m, 1H), 1.51 (m, 2H), 0.88 (dd, J = 6.0 and 5.7 Hz, 6H); 13C-NMR (100
MHz, CDCl3): δ 136.5 (C), 126.1 (C), 122.3 (CH), 119.7 (CH), 118.7 (CH), 113.9 (C), 111.5 (CH),
80.9 (CH2), 41.4 (CH2), 34.4 (CH), 25.4 (CH), 23.3 (CH), 21.5 (CH3); MS (EI) m/z (relative intensity):
246 (24) [M]+, 157 (26), 144 (36), 143 (71), 130 (100), 115 (24), 84 (19), 57 (31), 55 (25); HRMS-EI:
m/z [M]+ calcd for C14H18O2N2: 246.1368; found: 246.1365.
1
3-(2-Nitro-1-phenylethyl)-1H-indol-4-ol (4h): H-NMR (400 MHz, CDCl3): δ 7.94 (brs, 1H), 7.31-
7.24 (m, 4H), 7.18 (d, J = 9.4 Hz, 1H), 6.93 (t, J = 7.8 Hz, 1H), 6.85 (d, J = 8.1 Hz, 1H), 6.64 (s, 1H),
6.32 (d, J = 7.5 Hz, 1H), 5.43 (t, J = 8.1 Hz, 1H), 5.23 (dd, J = 12.7 and 6.6 Hz, 1H), 5.11 (brs, 1H),
4.87 (t, J = 11.8 Hz, 1H); 13C-NMR (100 MHz, CDCl3): δ 149.7 (C), 139.7 (C), 138.9 (C), 128.8 (CH),
127.8 (CH), 127.4 (CH), 123.4 (CH), 121.8 (C), 115.5 (CH), 114.7 (C), 104.8 (CH), 104.5 (CH), 79.8
(CH2), 42.1 (CH); MS (EI) m/z (relative intensity): 282 (54) [M]+, 236 (47), 235 (100), 234 (32), 222
(70), 220 (45), 117 (14), 103 (17), 77 (12); HRMS-EI: m/z [M]+ calcd for C16H14O3N2: 282.1004;
found: 282.1000.
1
3-(2-Nitro-1-phenylethyl)-1H-indol-4-yl acetate (4i): H-NMR (400 MHz, CDCl3): δ 8.16 (brs, 1H),
7.27-7.06 (m, 7H), 6.79 (d, J = 6.8 Hz, 1H), 6.65 (s, 1H), 5.19 (m, 1H), 5.01 (dd, J = 12.8 and 6.5 Hz,
1H), 4.85 (dd, J = 11.8 and 9.9 Hz, 1H), 2.21 (s, 3H); 13C-NMR (100 MHz, CDCl3): δ 170.3 (C), 143.8
(C), 139.0 (C), 138.9 (C), 129.0 (CH), 127.8 (CH), 127.7 (CH), 124.0 (CH), 122.8 (CH), 118.5 (CH),
113.2 (C), 112.6 (CH), 109.7 (CH), 79.9 (CH2), 42.0 (CH), 21.3 (CH3); MS (EI) m/z (relative
intensity): 324 (16) [M]+ , 282 (68), 236 (55), 235 (100), 222 (49); HRMS-EI: m/z [M]+ calcd for
C18H16N2O4: 324.1110; found: 324.1111.
1
3-(2-Nitro-1-phenylethyl)-1H-pyrrolo[2,3-b]pyridine (4j): H-NMR (400 MHz, CDCl3): δ 8.31
(d, J = 3.5 Hz, 1H), 7.87 (dd, J = 7.7 and 1.1 Hz, 1H), 7.33-7.30 (m, 5H), 7.20 (d, J = 3.5 Hz, 1H),
7.07 (dd, J = 7.7 and 4.7 Hz, 1H), 6.71 (dd, J = 9.2 and 6.1 Hz, 1H), 6.47 (d, J = 3.6 Hz, 1H), 5.37 (dd,
13
J = 13.4 and 9.2 Hz, 1H), 5.16 (dd, J = 13.4 and 6.1 Hz, 1H). C-NMR (100 MHz, CDCl3): δ 147.6
(C), 143.2 (CH), 135.9 (C), 129.3 (CH), 129.1 (CH), 129.0 (CH), 128.8 (CH), 127.0 (CH), 126.0 (CH),
121.0 (C), 116.6 (CH), 101.4 (C), 56.7 (CH2); MS (EI) m/z (relative intensity): 267 (5) [M]+, 221 (21),