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4-(2-chlorophenyl)-3-(phenylsulfonyl)-4H-benzo[h]chromen-2-amine (4k)
Solid, yield: 92%, m.p. 206–208 °C; IR (KBr) (m, cm-1): 3466, 3348, 3059, 1653,
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1627, 1262, 1199; H NMR (300 MHz, DMSO-d6) (d, ppm): 8.33 (d, J = 9 Hz,
1H), 7.85 (d, J = 6 Hz, 1H), 7.71 (d, J = 6 Hz, 2H), 7.66–7.47 (m, 6H), 7.39 (t,
J = 6 Hz, 2H), 7.27–7.17 (m, 3H), 7.10–7.06 (m, 2H), 5.55 (s, 1H); 13C NMR
(76 MHz, DMSO) (d, ppm): 158.70, 143.73, 142.96, 142.88, 133.14, 132.69,
131.71, 130.87, 129.83, 129.24, 128.62, 128.09, 128.02, 127.30, 127.23, 126.07,
125.26, 124.76, 123.10, 121.36, 119.78, 81.73, 38.19; MS (EI): m/z 447.1.
3-(phenylsulfonyl)-4-(o-tolyl)-4H-benzo[h]chromen-2-amine (4l)
Solid, yield: 90%, m.p. 219–221 °C; IR (KBr) (m, cm-1): 3462, 3335, 3066, 1654,
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1625, 1261, 1189; H NMR (300 MHz, DMSO-d6) (d, ppm): 8.32 (d, J = 9 Hz,
1H), 7.86 (d, J = 9 Hz, 1H), 7.66–7.44 (m, 8H), 7.33 (t, J = 9 Hz, 2H), 7.12 (d,
J = 9 Hz, 1H), 7.01–6.85 (m, 4H), 5.33 (s, 1H), 2.46 (s, 3H); 13C NMR (76 MHz,
DMSO) (d, ppm): 158.27, 158.22, 144.28, 144.01, 142.74, 134.81, 132.97, 132.47,
130.73, 129.51, 129.06, 128.07, 127.13, 126.77, 126.69, 126.09, 125.93, 124.56,
123.10, 121.30, 121.08, 83.10, 37.72, 19.67; MS (EI): m/z 427.2.
4-(2-fluorophenyl)-3-(phenylsulfonyl)-4H-benzo[h]chromen-2-amine (4m)
Solid, yield: 91%, m.p. 209–211 °C; IR (KBr) (m, cm-1): 3446, 3317, 1653, 1627,
1262, 1188; 1H NMR (300 MHz, DMSO-d6) (d, ppm): 8.32 (d, J = 9 Hz, 1H), 7.85
(d, J = 9.0 Hz, 1H), 7.72 (d, J = 9.0 Hz, 2H), 7.65–7.47 (m, 6H), 7.39 (t,
J = 9.0 Hz, 2H), 7.27–7.20 (m, 2H), 7.16–7.08 (m, 1H), 7.01–6.90 (m, 2H), 5.29 (s,
1H); 13C NMR (76 MHz, DMSO) (d, ppm): d 161.54, 158.89, 158.30, 143.95,
143.23, 133.10, 132.67, 132.55, 132.38, 130.30, 130.25, 129.27, 129.09, 128.98,
128.10, 127.25, 127.18, 126.04, 125.87, 124.88, 124.69, 123.07, 121.30, 119.64,
115.95, 115.66, 81.04, 35.72; MS (EI): m/z 431.2.
4-(3-chlorophenyl)-3-(phenylsulfonyl)-4H-benzo[h]chromen-2-amine (4n)
Solid, yield: 91%, m.p. 267–269 °C; IR (KBr) (m, cm-1): 3429, 3325, 3062, 1650,
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1622, 1262, 1190; H NMR (300 MHz, DMSO-d6) (d, ppm): 8.30 (d, J = 9.0 Hz,
1H), 7.87 (d, J = 9.0 Hz, 1H), 7.77–7.74 (m, 2H), 7.65–7.49 (m, 6H), 7.45–7.38 (m,
3H), 7.23–7.11 (m, 4H), 5.11 (s, 1H); 13C NMR (76 MHz, DMSO) (d, ppm):
158.82, 148.54, 144.07, 143.10, 133.40, 133.07, 132.76, 130.73, 129.27, 128.11,
127.42, 127.24, 127.18, 126.80, 126.37, 126.18, 126.13, 124.72, 123.14, 121.30,
120.95, 82.40, 41.05; MS (EI): m/z 447.2.
3-(phenylsulfonyl)-4-(p-tolyl)-4H-benzo[h]chromen-2-amine (4o)
Solid; yield: 90%, m.p. 267–269 °C; IR (KBr) (m, cm-1): 3457, 3338, 3019, 2917,
1652, 1625, 1260, 1184; 1H NMR (300 MHz, DMSO-d6) (d, ppm): 8.30 (d,
J = 9.0 Hz, 1H), 7.85 (d, J = 9.0 Hz, 1H), 7.73 (d, J = 6.0 Hz, 2H), 7.47 (m, 9H),
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