Compd. No.

Spectral Data

3a

FT-IR (KBr υ_max cm⁻¹): 3436 (NH), 3042, 2911, 2856 (CH), 1610 (C=N). 1H NMR (DMSO-d6) δ ppm: 2.50 (s, 3H, CH₃), 6.82 (s, 1H, H-3 indole), 6.97 - 7.07 (m, 4H. Ar-H), 7.25 (d, 1H, indole proton), 7.36 - 7.73 (m, 2H, indole proton), 7.76 (d, 1H, indole proton), 11.45 (s, 1H, NH). MS. m/z (%): 207 (M⁺, 100), 192 (3.12), 180 (3.18), 116 (1.99), 89 (20.56), 69 (29.66).

3b

FT-IR (KBr υ_max cm⁻¹): 3366, 3260, 3180 (NH₂, NH), 2915, 2855 (CH), 1599 (C=N). 1H NMR (DMSO-d6) δ ppm: 6.54 (s, 2H, NH₂), 6.70 - 7.21 (m, 5H, Ar-H and H-3 indole), 7.50 (d, 1H, indole proton), 7.71 - 7.82 (m, 2H, indole proton), 8.19 (d, 1H, indole proton), 9.13 (s, 1H, NH).

3c

FT-IR (KBr υ_max, cm⁻¹): 3182 (NH), 3057, 2977, 2867 (CH). 1H NMR (DMSO-d6) δ ppm: 6.46 (s, 1H, H-3 indole), 7.22 - 7.32 (m, 4H, Ar-H), 7.47 (d, 1H, indole proton), 8.21 (d, 1H, indole proton), 12.43 (s, 1H, NH).

3d

FT-IR (KBr υ_max cm⁻¹): 3426 (NH), 3037, 2917, 2851 (CH), 1671 (C=O). 1H NMR (DMSO-d6) δ ppm: 5.46 (s, 1H, H-3 indole proton), 7.14 - 7.95 (m, 9H, Ar-H and indole proton), 8.20 (s, 1H, NH). MS. m/z (%): 261 (M⁺, 18.48), 193 (2.80), 145 (18.01), 116 (13.51), 69 (100).

4

FT-IR (KBr, υ_max cm ⁻¹): 3181 (NH); 3063, 2978, 2868, 2713 (CH), 1672 (C=O), 1578 (C=N). 1H NMR (DMSO-d6) δ ppm: 7.22 - 7.32 (m, 4H, Ar-H), 7.50 (d, 1H, indole proton), 7.72 -7.82 (m, 2H, indole proton), 8.19 (d, 1H, indole proton), 9.95 (s, 1H, CHO), 12.40 (s, 1H, NH exchanged by D₂O). MS. m/z (%): 300 (M⁺, ‏,100 %), 220 (47), 219 (90.8), 190 (53), 165 (19.1), 143 (15.7).

5a

FT-IR (KBr, υ_max cm⁻¹): 3421, 3385, 3129 (NH₂, NH), 3048, 2965, 2860 (CH), 1607 (C=N), 1578 (C=C). 1H NMR (DMSO-d6) δ ppm: 7.05 - 7.29 (m, 4H, Ar- H), 7.46 (d, 1H, indole proton), 7.66 - 7.68 (m, 2H, indole proton), 8.42 (d, 1H, indole proton), 8.91 (s, 1H, =CH), 12.06 (s, 1H, NH exchanged by D₂O), 4.34 (s, 2H, NH₂ exchanged by D₂O).

5b

FT-IR (KBr, υ_max cm⁻¹): 3249 (NH), 3056, 2921, 2855 (CH), 1592 (C=N), 1532 (C=C). 1H NMR (DMSO-d6) δ ppm: 7.04 - 8.10 (m, 13H, Ar-H), 6.75 (s, 1H, =CH), 8.22 (s, 1H, NH exchanged by D₂O), 4.33 (s, 1H, NH exchanged by D₂O). MS. m/z (%): 391(M⁺ +1, 26.6), 389 (M⁺ - 1, 30.5), 233 (2.1), 298 (100), 284 (12.3), 271 (46.9), 190 (60.5).

5c

FT-IR (KBr, υ_max cm⁻¹): 3181 (NH), 3050, 2921 (CH), 1600 (C=N), 1573 (C=C). 1H NMR (DMSO-d6) δ ppm: 7.06 - 7.24 (m, 4H, Ar-H), 7.26 - 7.31 (m, 2H, benothiazole proton), 7.38 (d, 1H, benothiazole proton), 7.47 (d, 1H, indole proton),7.61-7.64 (m, 2H, indole proton), 7.73 (d, 1H, benothiazole proton), 8.36 (d, 1H, indole proton), 8.42 (s, 1H, =CH), 7.95 (s, 1H, NH exchanged by D₂O), 11.82 (s, 1H, NH exchanged by D₂O). MS. m/z (%): 447 (M⁺, 11.24), 313 (13.70), 296 (10.33), 204 (15.63), 150 (100).

7

FT-IR (KBr, υ_max cm⁻¹): 3207(NH), 3054, 3008, 2932, 2862 (CH), 1652 (C=O), 1611 (C=N), 1573 (C=C). 1H NMR (DMSO-d6) δ ppm: 7.14 - 8.80 (m, 14H, -Ar-H), 4.89 (s, 2H, CH₂), 8.90 (s, 1H, =CH), 11.92 (s, 1H, NH exchanged by D₂O), 12.05 (s, 1H, NH exchanged by D₂O).

8

FT-IR (KBr, υ_max cm ⁻¹): 3389, 3165 (NH), 3054, 2962, 2848 (CH), 1654 (C=O), 1604 (C=N). 1H NMR (DMSO-d6) δ ppm: 3.78 (s, 2H,CH₂), 7.16 - 7.28 (m, 5H, Ar-H and H-2 indole), 7.45 (d, 2H, indole proton), 7.56 - 7.89 (m, 4H, indole proton), 8.41 (d, 2H, indole proton), 8.90 (s, 1H, =CH), 4.31 (s, 1H, NH exchanged by D₂O), 12.03 (s, 2H, NH exchanged by D₂O). MS. m/z (%): 471 (M⁺, 0.94), 211 (4.96), 203 (74.04), 177 (12.11), 159 (13.50), 136 (37.99), 91 (100).

9

FT-IR (KBr, υ_max cm⁻¹): 3419, 3379, 3273 (NH), 3051, 2918, 2856 (CH), 1658 (C=O), 1604 (C=N). 1H NMR (DMSO-d6) δ ppm: 1.95 - 2.03 (m, 2H, CH₂), 2.20 (t, 2H,CH₂), 2.71(t, 2H, CH₂), 6.93 - 7.33 (m, 5H, Ar-H and H-2 indole), 7.42 (d, 2H, indole proton), 7.49 - 7.83 (m, 4H, indole proton), 8.12 (d,1H, indole proton), 8.35 (d, 1H, indole proton), 8.27 (s, 1H, =CH), 10.75 (s, 1H, NH exchanged by D₂O), 10.99 (s, 1H, NH exchanged by D₂O), 11.85 (s, 1H, NH exchanged by D₂O).

10

FT-IR (KBr, υ_max cm⁻¹): 3426, 3168 (NH), 3098, 3048, 2953, 2849 (CH), 1648 (C=O), 1608 (C=N). 1H NMR (DMSO-d6) δ ppm: 7.17 - 7.29 (m, 5H, Ar-H and H-3 benzofuran), 7.46 (d, 2H, indol and benzofuran),7.65 - 7.85 (m, 4H, indole and benzofuran), 8.42 (d, 2H, indole and benzofuran), 8.90 (s, 1H, =CH), 7.95 (s, 1H, NH exchanged by D₂O),12.04 (s, 1H, NH exchanged by D₂O). MS. m/z (%): 458 (M⁺, 0.10), 313 (0.11), 296 (5.76), 52 (66.65), 204 (63.53), 133 (43.88), 91 (100).

11

FT-IR (KBr, υ_max cm⁻¹): 3394, 3171 (NH), 3045, 2961, 2918 (CH), 1650 (C=O), 1604 (C=N), 2205 (CN). 1H NMR (DMSO-d6) δ ppm: 4.33 (s, 2H, CH₂), 7.16 - 7.28 (m,4H, Ar-H),7.44 (d, 1H, indole proton), 7.55 - 7.79 (m, 2H, indole proton), 8.11 (d, 1H, indole proton), 8.33 (s, 1H, N=CH), 11.33 (s, 1H, NH exchanged by D₂O), 11.93 (s, 1H, NH exchanged by D₂O). ¹³C NMR (DMSO-d6) δ ppm: 24.39 (CH₂), 116.19 (CN), 157.73 (C=N), 163.58 (CO), 107.75, 111.44, 111.66, 120.95, 122.14, 122.27, 123.13, 125.09, 130.07, 130.97, 131.16, 131.73, 131.89, 136.46.