Compound

Spectral Data

2a

IR, v (cm−1): 3433, 3240 and 3154 (NH, stretching), 2990, 2850 (=CH, stretching), 1522 (C=N, imine), 1595 (C=C, aromatic), 1114 (C=S). 1H-NMR (DMSO-d6, 400 M Hz, δ ppm): δH = 11.77 (s, 2H-N), 8.45 - 8.30 (m, 6H, pyridine ring and imine protons), 8.27 (s, 2N-H), 8.18 (s, 2N-H), 8.01 (t, J1 = J2 = 7.6 Hz, 2H, pyridine ring protons). 13C-NMR (DMSO-d6, 100 M Hz, δ ppm): δC = 178, 154, 153, 152, 138, 121.2, 121.1. LC-MS (m/z): 359 (M+H), 381 (M + Na) (100%).

2b

IR, v (cm−1): 3314 and 3155 (NH, stretching), 2960 and 2810 (>CH, stretching), 1515 (C=N, imine), 1573 (C=C, aromatic), 1076 (C=S). 1H-NMR (DMSO-d6, 400 M Hz, δ ppm): δH = 11.80 (s, 2N-H), 8.79 (t, J1 = J2 = 4 Hz, 2H, pyridine ring protons), 8.40 - 8.3 (m, 4H, pyridine ring and imine protons), 8.20 (s, 2N-H), 8.03 (t, J1 = J2 = 8 Hz, 2H, pyridine ring protons), 3.65 (m, 4H, methylene bridge), 1.2 (t, J1 = J2 = 7 Hz, 6H, methyl group). 13C-NMR (DMSO-d6, 100 M Hz, δ ppm): δC = 177, 155,153, 142, 138, 121.1, 121.0, 49, 14. LC-MS (m/z): 415 (M + H), 437 (M+Na) (100%).

2c

IR, v (cm−1): 3415, 3345 and 3220 (N-H, stretching), 2910 and 2870 (CH, stretching), 1470 (C=N, imine), 1557 (C=C, aromatic), 911 (C=S). 1H-NMR (DMSO-d6, 400 M Hz, δ ppm): δH = 11.40 (s, 2N-H), 8.40 - 8.3 (m, 4H, pyridine ring and imine protons), 8.10 - 7.90 (m, 4H, pyridine ring protons), 3.35 (s, 12H, methyl protons). 13C-NMR (DMSO-d6, 100 M Hz, δ ppm): δC = 180, 155, 153, 144,138, 120.9, 120.4, 42. LC-MS (m/z): 415 (M + H), 437 (M + Na) (100%).

2d

IR, v (cm−1): 3115 (NH, stretching), 2988 and 2849 (CH, stretching), 1510 (C=N, imine), 1580 (C=C, aromatic), 1041 (C=S). 1H-NMR (DMSO-d6, 400 M Hz, δppm): δH = 13.70 (s, 2N-H), 8.40 (d, J = 8 Hz, 2H), 8.35 (s, 2H, imine proton), 8.03 (t, J1 = J2 = 8 Hz, 2H, pyridine ring protons), 7.98 (d, J = 8 Hz, 2H, pyridine ring protons), 7.45 (d, J = 8 Hz, 2H, benzene ring protons), 7.35 (t, J1 = J2 = 8 Hz, 4H, benzene ring protons), 7.30 (t, J1 = J2 = 8 Hz, 4H, benzene ring protons). 13C-NMR (DMSO-d6, 100 M Hz, δ ppm): δC = 198, 155, 152, 146,138,136, 129.7, 129.0, 127, 122, 121, 38. LC-MS (m/z): 572.92 (M + H), 594.83 (M + Na) (100%).

2e

IR, v (cm−1): 3334 and 3089 (NH, stretching), 2940 (CH, stretching), 1505 (C=N, imine), 1615 (C=C, aromatic). 1H-NMR (DMSO-d6, 400 M Hz, δ ppm): δH = 11.20 (s, 2N-H), 8.35 (d, J = 6 Hz, 2H, pyridine ring protons), 8.11 - 8.05 (m, 4H, pyridine ring protons), 8.02 (t, J1 = J2 = 6 Hz, 2H, pyridine ring protons), 7.60 (d, J1 = 6 Hz, 4H, benzene ring protons), 7.30 (d, J = 6 Hz, 4H, benzene ring protons). 13C-NMR (DMSO-d6, 100 M Hz, δ ppm): δC = 154.4, 154.1, 148,139,138, 127, 126, 124, 120.3, 120.1, 112. LC-MS (m/z): 529.01 (M + H), (100%).

2f

IR, v (cm−1): 3290, 3149 and 3000 (NH, stretching), 2940 (CH, stretching), 1550 (C=N, imine), 1595 (C=C, aromatic), 1163 (C=S). 1H-NMR (DMSO-d6, 400 M Hz, δ ppm): δH = 12.20 (s, 2N-H), 10.30(s, 2N-H), 8.55 (d, J = 8 Hz, 2H, pyridine ring protons), 8.40 (d, J = 8 Hz, 2H, pyridine ring protons), 8.3 (d, J1 = 8 Hz, 2H, imine protons), 8.11 (t, J1 = J2 = 8 Hz, 2H, pyridine ring proton), 7.55 (d, J1 = J2 = 8 Hz, 4H, benzene ring protons), 7.40 (t, J1 = J2 = 8 Hz, 4H, benzene ring protons), 7.25 (t, J1 = J2 = 8 Hz, 2H, benzene ring protons). 13C-NMR (DMSO-d6, 100 M Hz, δ ppm): δC = 176, 155, 153, 143, 139, 138, 128, 126.6, 126.1, 121.5, 121.4. LC-MS (m/z): 533 (M + Na), 551(M + K) (100%).

2g

IR, v (cm−1): 3264, 3120 (NH, stretching), 2946 (CH, stretching), 1505 (C=N, imine), 1556 (C=C, aromatic), 1042 (C=S). 1H-NMR (DMSO-d6, 400 M Hz, δ ppm): δH = 11.80 (s, 2N-H), 10.10 (s, 2N-H), 8.48 (d, J = 8 Hz, 2H, pyridine ring protons), 8.33 (d, J = 8 Hz, 2H, imine protons), 8.14 (d, J = 8 Hz, 2H, pyridine ring protons), 8.00 (t, J1 = J2 = 8 Hz, 2H, pyridine ring protons), 5.10 (s, broad, 4H, NH2 group). 13C-NMR (DMSO-d6, 100 M Hz, δ ppm): δC = 176, 154, 153, 142, 138, 126.2, 121. LC-MS (m/z): 389 (M+H).

2h

IR, v (cm−1): 3360, 3053 (NH, stretching), 2920 (CH, stretching), 1562 (C=C, aromatic). 1H-NMR (DMSO-d6, 400 M Hz, δ ppm): δH = 8.52 (d, J = 4 Hz, 1H, pyridine ring proton), 8.38 - 8.5 (m, 2H, pyridine ring protons), 8.32 (s, 1H, thiazolyl C-H proton), 8.30 - 8.08 (m, 3H, pyridine ring and thiazolyl C-H proton protons), 7.50 (d, J = 4 Hz, 1H, benzene ring proton), 7.65 - 7.40 (m, 3H, benzene ring),7.25 (s, broad, 1 N-H thiazolyl ring proton), 7.10 (d, J = 4 Hz, 1H, benzene ring proton), 6.90 (t, J1 = J2 = 4 Hz, 1H, benzene ring proton), 6.75 (d, J = 4 Hz, 1H, benzene ring proton), 6.67 (t, J1 = J2 = 4 Hz, 1H, benzene ring proton), 6.5 (s, 1H, N-H proton). 13C-NMR (DMSO-d6, 100 M Hz, δppm): δC = 169, 162, 155, 154, 153, 150, 148, 139.7, 139.3, 135, 127, 126.6, 126.0, 124, 123.8, 123.1, 121.7, 121.2, 121.1, 120, 119, 109. LC-MS (m/z): 449 (M + Na).