3550
G. K. Pathe, N. Ahmed
Paper
Synthesis
GC-MS: m/z = 168, 163 [M+] (C9H9NO2), 146, 114, 102, 80 (100%).
13C NMR (125 MHz, CDCl3): δ = 153.61, 146.47, 141.96, 141.35,
134.47, 130.03, 129.03, 128.85, 127.34, 127.12, 122.96, 122.60,
117.43, 107.37, 79.79.
1-Methoxy-4-[(E)-2-nitrovinyl]benzene (6c)
GC-MS: m/z = 253 [M+] (C15H11NO3), 236, 207, 178 (100%), 152, 89, 77,
Yellow solid; yield: 155 mg (87%); mp 86–88 °C.
63.
IR (KBr): 3104, 2904, 2838, 1495, 1307 cm–1
.
1H NMR (500 MHz, CDCl3): δ = 7.97 (d, J = 13.5 Hz, 1 H), 7.57 (d,
J = 13.5 Hz, 1 H), 7.38–7.35 (m, 1 H), 7.15–7.13 (m, 1 H), 7.05–7.03 (m,
2 H), 3.85 (s, 3 H).
13C NMR (125 MHz, CDCl3): δ = 157.12, 139.54, 136.27, 130.77,
122.36, 115.19, 57.45.
2-(4-Chlorophenyl)-3-nitro-2H-chromene (2d)
Yellow solid; yield: 249 mg (87%); mp 150 °C.
IR (KBr): 3076, 2923, 1639, 1495, 1323, 1214 cm–1
1H NMR (500 MHz, CDCl3): δ = 8.05 (s, 1 H), 7.35–7.27 (m, 6 H), 6.99
(t, J = 7.5 Hz, 1 H), 6.86 (d, J = 8 Hz, 1 H), 6.57 (s, 1 H).
13C NMR (125 MHz, CDCl3): δ = 156.96, 147.43, 145.11, 139.90,
.
GC-MS: m/z = 179 [M+] (C9H9NO3), 132, 118, 103, 89 (100%).
128.84, 128.80, 127.33, 126.58, 122.91, 122.55, 117.43, 115.91, 79.47.
GC-MS: m/z = 287 [M+] (C15H10ClNO3), 270, 257, 241 (100%), 205, 178,
1,2-Dimethoxy-4-[(E)-2-nitrovinyl]benzene (7c)
Yellow solid; yield: 177 mg (85%); mp 138–140 °C.
89, 77, 63.
IR (KBr): 3128, 2958, 2923, 1500, 1334 cm–1
.
1H NMR (500 MHz, CDCl3): δ = 7.96 (d, J = 13.5 Hz, 1 H), 7.53 (d,
J = 13.5 Hz, 1 H), 7.18–7.16 (m, 1 H), 7.00–6.91 (m, 2 H), 3.95 (s, 3 H),
3.90 (s, 3 H).
2-(2-Chlorophenyl)-3-nitro-2H-chromene (3d)
Yellow solid; yield: 243 mg (85%); mp 90–92 °C.
IR (KBr): 3069, 2923, 1644, 1511, 1327, 1107 cm–1
.
13C NMR (125 MHz, CDCl3): δ = 149.87, 149.10, 138.54, 135.27,
122.36, 121.12, 115.89, 115.06, 57.87.
GC-MS: m/z = 209 [M+] (C10H11NO4), 163, 162, 147, 119, 77 (100%).
1H NMR (500 MHz, CDCl3): δ = 8.15 (s, 1 H), 7.48 (dd, J = 1, 9.5 Hz, 1
H), 7.34 (dd, J = 2, 8 Hz, 1 H), 7.32–7.27 (m, 3 H), 7.19 (dd, J = 2, 8 Hz, 1
H), 7.07 (s, 1 H), 7.00 (dt, J = 1, 9.1 Hz, 1 H), 6.82 (d, J = 8 Hz, 1 H).
13C NMR (125 MHz, CDCl3): δ = 153.61, 146.74, 144.99, 139.94,
134.77, 129.92, 128.99, 128.72, 128.59, 127.21, 122.34, 121.94,
116.91, 114.47, 79.59.
GC-MS: m/z = 289, 287 [M+] (C15H10ClNO3), 270, 257, 241, 205, 176,
146 (100%), 89, 76, 63.
1,2,3-Trimethoxy-5-[(E)-2-nitrovinyl]benzene (8c)
Yellow solid; yield: 210 mg (88%); mp 115–116 °C.
IR (KBr): 3104, 2935, 2832, 1503, 1323 cm–1
.
1H NMR (500 MHz, CDCl3): δ = 7.93 (d, J = 13.6 Hz, 1 H), 7.53 (d,
J = 13.6 Hz, 1 H), 6.75 (s, 2 H), 3.91 (s, 3 H), 3.90 (s, 6 H).
13C NMR (125 MHz, CDCl3): δ = 155.12, 143.62, 137.12, 136.65,
129.87, 106.00, 61.17, 55.76.
GC-MS: m/z = 239 [M+] (C11H13NO5), 191, 176, 149, 120, 63 (100%), 53.
2-(4-Bromophenyl)-3-nitro-2H-chromene (4d)
Yellow solid; yield: 291 mg (88%); mp 162 °C.
IR (KBr): 3078, 2923, 1639, 1496, 1323, 1065 cm–1
.
1H NMR (500 MHz, CDCl3): δ = 8.23 (s, 1 H), 8.19 (d, J = 8.5 Hz, 1 H),
8.13 (s, 1 H), 7.71 (d, J = 8 Hz, 1 H), 7.52 (t, J = 8 Hz, 1 H), 7.36 (t, J = 7.5
Hz, 2 H), 7.05 (t, J = 7.5 Hz, 1 H), 6.90 (d, J = 8.5 Hz, 1 H), 6.66 (s, 1 H).
13C NMR (125 MHz, CDCl3): δ = 153.36, 146.74, 144.02, 141.16,
133.48, 132.27, 128.94, 128.72, 127.36, 124.24, 123.16, 122.48,
117.41, 79.11.
4-[(E)-2-Nitrovinyl]phenol (9c)
Yellow solid; yield: 148 mg (90%); mp 162–164 °C.
IR (KBr): 3370, 3108, 1483, 1339 cm–1
1H NMR (500 MHz, CDCl3): δ = 7.96 (d, J = 13.6 Hz, 1 H), 7.51 (d,
J = 13.6 Hz, 1 H), 7.47–7.45 (m, 2 H), 6.91–6.89 (m, 2 H).
.
13C NMR (125 MHz, CDCl3): δ = 157.87, 140.11, 139.52, 130.77,
GC-MS: m/z = 333, 331 [M+] (C15H10BrNO3), 287, 285, 205 (100%), 176,
123.12, 115.10.
146, 89, 76, 63.
GC-MS: m/z = 166, 165 [M+] (C8H7NO3), 148, 118 (100%), 91, 65.
3-Nitro-2-p-tolyl-2H-chromene (5d)
Yellow solid; yield: 229 mg (86%); mp 136–138 °C.
1-Nitro-3-[(E)-2-nitrovinyl]benzene (10c)
Light brown solid; yield: 178 mg (92%); mp 120–122 °C.
IR (KBr): 3078, 2924, 1646, 1506, 1321, 1114 cm–1
.
IR (KBr): 3100, 2832, 1522, 1349 cm–1
1H NMR (500 MHz, CDCl3): δ = 7.96 (d, J = 13.7 Hz, 1 H), 7.56 (d,
J = 13.7 Hz, 1 H), 7.50–7.48 (m, 2 H), 7.44–7.43 (m, 2 H).
13C NMR (125 MHz, CDCl3): δ = 148.13, 140.10, 139.54, 136.27,
133.61, 130.71, 122.35, 122.12.
.
1H NMR (500 MHz, CDCl3): δ = 8.04 (s, 1 H), 7.32–7.28 (m, 2 H), 7.25–
7.24 (m, 2 H), 7.11 (d, J = 8 Hz, 2 H), 6.98 (dt, J = 1, 7.5 Hz, 1 H), 6.84
(dd, J = 1, 7.5 Hz, 1 H), 6.54 (s, 1 H), 2.30 (s, 3 H).
13C NMR (125 MHz, CDCl3): δ = 153.68, 148.83, 145.95, 140.06,
131.42, 129.70, 128.80, 127.32, 127.05, 122.86, 122.59, 117.42, 79.71,
21.56.
GC-MS: m/z = 194 [M+] (C8H6N2O4), 147, 108, 102 (100%), 89, 76, 63.
GC-MS: m/z = 267 [M+] (C16H13NO3), 250, 237, 221 (100%), 178, 146,
91, 77, 65.
3-Nitro-2-phenyl-2H-chromene (1d)
Yellow solid; yield: 215 mg (85%); mp 98–100 °C.
2-(4-Methoxyphenyl)-3-nitro-2H-chromene (6d)
IR (KBr): 3071, 1646, 1507, 1328, 1215 cm–1
.
Yellow solid; yield: 246 mg (87%); mp 158–160 °C.
1H NMR (500 MHz, CDCl3): δ = 8.05 (s, 1 H), 7.38–7.36 (m, 2 H), 7.33–
7.30 (m, 5 H), 7.01–6.98 (m, 1 H), 6.87–6.85 (m, 1 H), 6.58 (s, 1 H).
IR (KBr): 2945, 1645, 1507, 1326, 1179 cm–1
.
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2015, 47, 3542–3552