12

FT-IR (KBr, υ_max cm⁻¹): 3391, 3311, 3184 (NH), 3047, 2960, 2918 (CH), 1667 (C=O), 1603 (C=N), 2212 (CN). 1H NMR (DMSO-d6) δ ppm: 2.29 (s, 3H, CH₃), 7.18 - 7.44 (m, 8H, Ar-H), 7.46 (d,1H, indole proton), 7.55 - 7.79 (m, 2H, indole proton), 8.19 (d, 1H, indole proton), 8.38 (s, 1H, = CH), 11.24 (s, 1H, NH exchanged by D₂O), 11.33 (s, 1H, NH exchanged by D₂O), 11.91 (s, 1H, NH exchanged by D₂O). ¹³C NMR (DMSO-d6) δ pm: 10.65 (CH₃), 116.19 (CN), 155.22 (C=N), 159 (C=NNH), 111.41, 119.24, 122.18, 129.79, 130.07, 130.85, 131.04, 131.15, 131.24, 131.79, 133.31, 136.46, 136.46, 136.76.

13a

FT-IR (KBr, υ_max cm⁻¹): 3335, 3126(NH), 3055, 2921 (CH), 1686 (C=O), 2204 (CN). 1H NMR (DMSO-d6) δ ppm: 7.19-8.57 (m, 19H, Ar-H and H-5 pyrazole ring), 8.96 (s, 1H, =CH), 9.21 (s, 1H, N=CH); 11.73 (s, 1H, NH exchanged by D₂O), 12.04 (s, 1H, NH exchanged by D₂O). MS, m/z (%), 611 (M⁺, 0.63), 392 (1.05), 379 (0.51), 358 (11.477), 327 (1.42), 217 (33.11), 77.02 (100).

13b

FT-IR (KBr,υ_max cm ⁻¹): 3233, 3166 (NH), 3091, 2971 (CH), 1682 (C=O), 2208 (CN). 1H NMR (DMSO-d6) δ ppm: 7.22 - 8.39 (m, 12H, Ar-H), 8.68 (s, 1H, =CH), 8.88 (s, 1H, N=CH), 11.93 (s, 1H, NH exchanged by D₂O), 12.42 (s, 1H, NH exchanged by D₂O).

14

FT-IR (KBr, υ_max cm⁻¹): 3372, 3155 (NH), 3093, 2930, 2853 (CH), 1712 (C=O). 1H NMR (DMSO-d6) δ ppm: 5.17 (s, 1H, H-4 coumarin ring), 6.56 - 8.22 (m, 12 H, Ar-H), 8.72 (s, 1H, N=CH), 11.44 (s, 1H, NH exchanged by D₂O), 11.56 (s, 1H, NH exchanged by D₂O), 12.14 (s, 1H, NH exchanged by D₂O). MS. m/z (%): 485(M⁺, 0.30), 470 (0.4), 457 (0.4), 442 (0.1), 417 (3.00), 271 (100), 191(61.6), 165 (77.9).

15

FT-IR (KBr, υ_max cm⁻¹): 3475, 3396, 3369, 3234, 3180 (2NH_2, NH), 3059, 2934, 2838 (CH), 1721, 1670 (2 C=O), 2210 (CN). 1H NMR (DMSO-d6) δ ppm: 1.26 (t, 3H, CH₂-CH₃), 4.23 (q, 2H, CH₂-CH₃), 7.22 - 8.225 (m, 12 H, Ar-H and 2 NH₂), 8.25 (s, 1H, N= CH), 12.91 (s, 1H, NH exchanged by D₂O), 12.45 (s, 1H, NH exchanged by D₂O).

16

FT-IR (KBr, υ_max cm⁻¹): 3395, 3269, 3164 (NH₂, NH), 3049, 2974, 2866 (CH), 1665 (C=O), 1237 (C=S). 1H NMR (DMSO-d6) δ ppm: 7.16 - 8.48 (m, 15 H, Ar-H and NH₂), 8.90(s, 1H, N=CH), 11.00 (s, 1H, NH exchanged by D₂O), 12.43 (s, 1H, NH exchanged by D₂O). ¹³C NMR (DMSO-d6) δ ppm: 147.39 (C=N), 153 (C-NH₂), 161.36 (CO), 183.91 (CS), 112.10, 113.61, 121.01, 122.38, 123.44, 125.7, 126.93, 130.7, 131.14, 131.87, 135.88, 136.51, 136.51, 141.72.

17

FT-IR (KBr, υ_max, cm⁻¹): 3129 (NH), 3091, 3052, 2947, 2860 (CH), 1681 (C=O), 1239 (C=S). 1H NMR (DMSO-d6) δ ppm: 2.25 (s, 3H, CH₃), 7.05-7.81(m, 13 H, Ar-H), 8.22(s, 1H, =CH), 12.40 (s, 1H, NH exchanged by D₂O).

18

FT-IR (KBr, υ_max cm⁻¹): 3269 (NH), 3090, 2970, 2869 (CH). 1H NMR (DMSO-d6) δ ppm: 6.85 (s, 1H, N=CH), 6.98-7.32 (m, 10 H, Ar-H and H-5 thiazole ring), 7.50 (d, 1H, indole proton), 7.65 - 7.82 (m, 2H, indole proton), 8.20 - 8.22 (d, 1H, indole proton), 12.43 (s, 1H, NH exchanged by D₂O).

19

FT-IR (KBr, υ_max cm⁻¹): 3127 (NH), 3084, 2967, 2862 (CH), 1671, 1718 (2C=O). 1H NMR (DMSO-d6) δ ppm: 7.22 - 7.32 (m, 5 H, Ar-H and H-4 chromene), 7.44 (d, 2H, indole and chromene), 7.70 - 7.92 (m, 4H, indole and chromene), 7.93 - 7.97 (m, 2H, CH= CH), 8.00 - 8.22 (d, 2H, indole and chromene), 12.43 (s, 1H, NH exchanged by D₂O).

20a

FT-IR (KBr, υ_max cm⁻¹): 3466, 3310, 3149 (NH₂, NH), 3048, 2970, 2865 (CH), 1688 (C=O) and 2203 (CN). 1H NMR (DMSO-d6) δ ppm: 7.22 - 7.32 (m, 6 H, Ar-H and NH₂ proton), 7.47 - 7.83 (m, 3H, indole proton), 7.96 (d, 1H, indole proton), 8.22 (s, 1H, C=CH), 12.43 (s, 1H, NH exchanged by D₂O).

20b

FT-IR (KBr, υ_max cm⁻¹): 3269 (NH), 3047, 2973, 2861 (CH), 2208 (CN), 1708 (C=O). 1H NMR (DMSO-d6) δ ppm: 1.03 (t, 3H, CH₂CH₃), 4.23 (q, 2H, CH₂ CH₃), 7.29 - 7.35 (m, 4H, Ar-H), 7.56 - 7.86 (m, 3H, indole proton), 8.15 - 8.17 (d, 1H, indole proton), 8.25 (s, 1H, =CH); 4.34 (s, 1H, NH exchanged by D₂O). MS. m/z (%): 395 (M⁺, 11.8), 321 (44.6), 242 (100), 215 (17.6), 214 (32.8).

21

FT-IR (KBr, υ_max cm⁻¹): 3303 (NH), 2203(CN), 3052, 2961, 2921, 2859 (CH), 1672 (C=O). 1H NMR (DMSO-d6) δ ppm: 4.20 (d, 1H, pyrazoline), 6.11 (d, 1H, pyrazoline), 6.97 - 7.00 (m, 4H, Ar-H), 7.02 - 7.87 (m, 3H, indole proton), 7.97 (d, IH, indole proton), 10.18 (s, 1H, NH exchanged by D₂O), 11.41 (s, 1H, NH exchanged by D₂O), 12.22 (s, 1H, NH exchanged by D₂O).

22

FT-IR (KBr, υ_max cm ⁻¹): 3384 (NH), 2212 (CN), 3054, 2957, 2852 (CH). 1H NMR (DMSO-d6) δ ppm: 7.21 - 7.32 (m, 4H, Ar-H), 7.57 - 7.95 (m, 8H, indole and benzimidazole proton), 8.31 (s, 1H, =CH), 12.57 (s, 1H, NH exchanged by D₂O), 12.88 (s, 1H, NH exchanged by D₂O).

23

FT-IR (KBr, υ_max cm⁻¹): 3355 (OH), 3179 (NH), 1623, 1707 (2C=O), 3095, 2974, 2865 (CH), 1242 (C=S). 1H NMR (DMSO-d6) δ ppm: 4.71 (s, 2H, CH₂), 7.32 - 7.33 (m, 4H, Ar-H), 7.50 (d, 1H, indole proton), 7.66 - 7.79 (m, 2H, indole proton), 7.99 (s, 1H, CH=C), 8.19 (d, 1 H, indole proton), 12.43 (s, 1H, NH exchanged by D₂O), 12.60 (s, 1H, OH exchanged by D₂O). MS. m/z (%): 473 (M⁺, 1.4), 472 (M⁺-1, 4.1), 456 (0.2), 382 (0.7), 327 (15.6), 271 (100), 202 (4.9).