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Chapter 6
Synthesis of benzodiazepines
1-cyclohexyl-5-(4-fluorophenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one ADZ-04i.
Yellow solid, mp 137-139 ° C; R f 0.35 (8:2 hexane-EtOAc); IR (KBr): 3074, 2856,
2828, 1694, 1635, 1482, 1343, 1298, 1058, 840, 732 cm -1 ; MS (m/z): 333 [M + ]; Anal.
Calcd for C 21 H 21 FN 2 O: C, 74.98; H, 6.29; N, 8.33; Found: C, 74.90; H, 6.25; N, 8.37.
5-(4-fluorophenyl)-1-(4-nitrobenzyl)-1H-benzo[e][1,4]diazepin-2(3H)-one ADZ-
04j. Yellow solid, mp 157-159 ° C; R f 0.49 (8:2 hexane-EtOAc); IR (KBr): 3241, 3068,
3015, 2956, 2881, 1330, 1268, 1054, 834, 830,756, 701 cm -1 ; MS (m/z): 389 [M + ];
Anal. Calcd for C 21 H 16 FN 3 O 3 : C, 67.86; H, 4.14; N, 10.79; Found: C, 67.90; H, 4.15;
N, 10.77.
3-benzylidene-5-(4-fluorophenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one ADZ-05a.
Yellow solid, mp 192-195 ° C; R f 0.25 (8:2 hexane-EtOAc); IR (KBr): 3450, 3110,
3054, 2990, 2932, 2854, 1456, 1305, 1250, 1005, 805, 732, 695 cm -1 ; 1 H NMR (400
MHz, DMSO): δ 6.39 (s. 1H, CH), 7.08-7.12 (m, 1H, Ar), 7.21-7.37 (m, 7H, Ar),
7.46-7.53 (m, 3H, Ar), 7.76-7.79 (m, 2H, Ar), 8.15 (s, 1H, NH); 13 C NMR: (100 MHz,
DMSO): δ 115.25, 115.46, 118.09, 121.39, 122.58, 126.58, 126.74, 127.50, 128.07,
128.19, 128.92, 129.90, 129.95, 131.80, 131.89, 134.41, 134.44, 134.75, 138.93,
140.54, 162.45, 164.26, 164.94, 171.00; MS (m/z): 342 [M + ]; Anal. Calcd for
C 22 H 15 FN 2 O: C, 77.18; H, 4.42; N, 8.18; Found: C, 77.20; H, 4.45; N, 8.22.
5-(4-fluorophenyl)-3-(3-nitrobenzylidene)-1H-benzo[e][1,4]diazepin-2(3H)-one
ADZ-05b. Yellow solid, mp 202-204 ° C; R f 0.28 (8:2 hexane-EtOAc); IR (KBr): 3390,
3072, 2856, 2832, 1684, 1635, 1482, 1356, 1298, 830, 750, 700 cm -1 ; 1 H NMR (300
MHz, DMSO): δ 6.44 (s. 1H, CH), 7.06-7.11 (m, 1H, Ar), 7.24-7.40 (m, 4H, Ar),
7.50-7.67 (m, 3H, Ar), 7.82-7.93 (m, 3H, Ar), 8.08-8.11 (d, 1H, J=8.1Hz, Ar), 8.58 (s,
1H, NH); 13 C NMR: (100 MHz, DMSO): δ 120.15, 120.47, 121.01, 126.53, 126.79,
127.80, 129.01, 131.73, 134.32, 135.48, 137.11, 137.15, 137.24, 139.46, 141.68,
143.84, 147.81, 152.92, 175.11; MS (m/z): 387 [M + ]; Anal. Calcd for C 22 H 14 FN 3 O 3 :
C, 68.21; H, 3.64; N, 10.85; Found: C, 68.20; H, 3.67; N, 10.83.
Department of Chemistry, Saurashtra University, Rajkot-360005 220