Journal of Chemistry

Research Article

Synthesis of Novel 1,2,4-Triazole Derivatives as Antimicrobial Agents via the Japp-Klingemann Reaction: Investigation of Antimicrobial Activities

Table 2

Spectral data of synthesized compounds.
Comp.IR cm−1 1H-NMR δ ppm 13C-NMRMS m/e
2a3449–3348 (NH), 1709 and 1657 (C=O), 1603 (C=N)2.20 (s, 3H, acetyl CH3), 2.45 (s, 3H, CH3), 3.67 (dd, 1H, [HA] CH2, J = 10.12 Hz), 4.25 (dd, 1H, [HB] CH2, J = 12.25 Hz), 4.89 (m, 1H, [HX] CH, = 4 Hz, = 7 Hz), 5.93 (s, 2H, NH2), 6.61–8.64 (m, 13H, Ar-H), 9.99 (s, 1H, N=CH) 479
2b3450–3348 (NH), 1710, 1654 (C=O), 1605 (C=N)2.24 (s, 3H, acetyl CH3), 2.40 (s, 3H, CH3), 3.70 (dd, 1H, [HA] CH2, J = 13.05 Hz), 4.23 (dd, 1H, [HB] CH2, J = 12.05 Hz), 4.90 (m, 1H, [HX] CH, = 4.80 Hz, = 8.43 Hz), 7.21–8.67 (m, 12H, Ar-H), 9.60 (s, 2H, NH2, D2O exchangeable), 9.109 (s, 1H, N=CH) 513 (M+), 515 (M+2)
2c3444–3339 (NH), 1705 and 1650 (C=O), 1600 (C=N)2.20 (s, 3H, acetyl CH3), 2.43 (s, 3H, CH3), 3.68 (dd, 1H, [HA] CH2, J = 11.05 Hz), 4.20 (dd, 1H, [HB] CH2, J = 13.05 Hz), 4.2 (m, 1H, [HX] CH, = 4.45 Hz, = 7.75 Hz), 7.25–8.70 (m, 12H, Ar-H), 9.55 (s, 2H, NH2, D2O exchangeable), 9.68 (s, 1H, N=CH) 513 (M+), 515 (M+2)
2d3434–3324 (NH), 1701, 1652 (C=O), 1604 (C=N)2.22 (s, 3H, acetyl CH3), 2.45 (s, 3H, CH3), 3.62 (dd, 1H, [HA] CH2, J = 12.03 Hz), 4.15 (dd, 1H, [HB] CH2, J = 11.1 Hz), 4.89 (m, 1H, [HX] CH, = 7 Hz, = 4 Hz), 7.15–8.68 (m, 12H, Ar-H), 9.45 (s, 2H, NH2, D2O exchangeable), 9.70 (s, 1H, N=CH) 513 (M+), 515 (M+2)
2e3455–3335 (NH), 1705, 1654 (C=O), 1600 (C=N)2.25 (s, 3H, acetyl CH3), 2.30 (s, 3H, CH3), 2.50 (s, 3H, CH3), 3.60 (dd, 1H, [HA] CH2, J = 11.80 Hz), 4.20 (dd, 1H, [HB] CH2, J = 11.1 Hz), 4.89 (m, 1H, [HX] CH, = 7 Hz, = 4 Hz), 6.50–7.108 (m, 12H, Ar-H), 7.1 (s, 2H, NH2, D2O exchangeable), 8.11 (s, 1H, N=CH) 493
2f3460 (OH), 3449–3348 (NH), 1712, 1657 (C=O), 1603 (C=N)2.22 (s, 3H, acetyl CH3), 2.47 (s, 3H, CH3), 3.65 (dd, 1H, [HA] CH2, J = 12.10 Hz), 4.25 (dd, 1H, [HB] CH2, J = 12.06 Hz), 4.109 (m, 1H, [HX] CH, = 3.32 Hz, = 4.32 Hz), 5.15 (s, 1H, OH, D2O exchangeable), 7.25–8.65 (m, 12H, Ar-H), 9.50 (s, 2H, NH2, D2O exchangeable), 9.69 (s, 1H, N=CH) 495
2g3439–3325 (NH), 1715, 1654 (C=O), 1605 (C=N)2.30 (s, 3H, acetyl CH3), 3.72 (s, 3H, –OCH3), 2.47 (s, 3H, CH3), 3.65 (dd, 1H, [HA] CH2, J = 10.10 Hz), 4.26 (dd, 1H, [HB] CH2, J = 12.06 Hz), 4.79 (m, 1H, [HX] CH, = 4 Hz, = 7 Hz), 6.50-7.50 (m, 12H, Ar-H), 8.23 (s, 2H, NH2, D2O exchangeable), 8.55 (s, 1H, N=CH) 586
3a1711, 1658, 1605 (C=O), 1519 (C=N)1.97 (s, 3H, acetyl CH3), 2.37 (s, 6H, CH3), 2.46 (s, 3H, C5–CH3), 3.31 (dd, 1H, [HA] CH2, J = 11.05 Hz), 3.69 (dd, 1H, [HB] CH2, J = 12.06 Hz), 4.63 (m, 1H, [HX] CH, = 4.55 Hz, = 8.43 Hz), 5.53 (s, 1H, NH (D2O exchangeable)), 7.19–8.24 (m, 13H, Ar-H), 9.99 (s, 1H, N=CH) 590
3b3455 (NH), 1710, 1658, 1604 (C=O), 1532 (C=N)1.72 (s, 3H, acetyl CH3), 2.30 (s, 6H, CH3), 2.40 (s, 3H, C5–CH3), 3.20–3.25 (dd, 1H, [HA] CH2, J = 12.03 Hz), 3.71 (dd, 1H, [HB] CH2, J = 12.05 Hz), 4.79 (m, 1H, [HX] CH, = 3.34 Hz, = 10.11 Hz), 5.55 (s, 1H, NH (D2O exchangeable)), 7.25–8.30 (m, 12H, Ar-H), 8.64 (s, 1H, N=CH) 624 (M+), 626 (M+2)
3c3445 (NH), 1715, 1656, 1600 (C=O), 1524 (C=N)1.69 (s, 3H, acetyl CH3), 2.30 (s, 6H, CH3), 2.45 (s, 3H, C5–CH3), 3.24–3.27 (dd, 1H, [HA] CH2, J = 12.00 Hz), 3.71 (dd, 1H, [HB] CH2, J = 12.05 Hz), 4.79 (m, 1H, [HX] CH, = 7 Hz, = 4 Hz), 5.58 (s, 1H, NH (D2O exchangeable)), 6.50–7.108 (m, 13H, Ar-H), 8.00 (s, 1H, N=CH) 624 (M+), 626 (M+2)
3d3455 (NH), 1708, 1654, 1604 (C=O), 1530 (C=N)1.75 (s, 3H, acetyl CH3), 2.35 (s, 6H, CH3), 2.49 (s, 3H, C5–CH3), 3.27–3.29 (dd, 1H, [HA] CH2, J = 11.05 Hz), 3.75 (dd, 1H, [HB] CH2, J = 12.07 Hz), 4.80 (m, 1H, [HX] CH, = 7.73 Hz, = 4.47 Hz), 5.57 (s, 1H, NH (D2O exchangeable)), 6.55–7.75 (m, 13H, Ar-H), 8.13 (s, 1H, N=CH) 624 (M+), 626 (M+2)
3e3455 (NH), 1710, 1658, 1604 (C=O), 1532 (C=N)1.68 (s, 3H, acetyl CH3), 2.36 (s, 6H, CH3), 2.40 (s, 3H, C5–CH3), 2.54 (s, 3H, CH3), 3.25–3.28 (dd, 1H, [HA] CH2, J = 13.00 Hz), 3.107 (dd, 1H, [HB] CH2, J = 12.07 Hz), 4.89 (m, 1H, [HX] CH, = 5.54 Hz, = 8.44 Hz), 5.56 (s, 1H, NH (D2O exchangeable)), 6.50–7.109 (m, 13H, Ar-H), 8.15 (s, 1H, N=CH) 604
3f3550 (OH), 3457 (NH), 1713, 1658, 1604 (C=O), 1530 (C=N)1.72 (s, 3H, acetyl CH3), 2.37 (s, 6H, CH3), 2.45 (s, 3H, C5–CH3), 3.14–3.31 (dd, 1H, [HA] CH2, J = 10.05 Hz), 3.72 (dd, 1H, [HB] CH2, J = 13.06 Hz), 4.75 (m, 1H, [HX] CH, = 4.43 Hz, = 8.88 Hz), 5.53 (s, 1H, NH (D2O exchangeable)), 5.60 (s, 1H, OH) (D2O exchangeable), 7.20–8.25 (m, 13H, Ar-H), 9.00 (s, 1H, N=CH) 606
3g3455 (NH), 1708, 1654, 1604 (C=O), 1532 (C=N)1.75 (s, 3H, acetyl CH3), 2.35 (s, 6H, CH3), 2.49 (s, 3H, C5–CH3), 3.75 (s, 3H, –OCH3), 3.27–3.29 (dd, 1H, [HA] CH2, J = 12.05 Hz), 3.75 (dd, 1H, [HB] CH2, J = 12.07 Hz), 4.80 (m, 1H, [HX] CH, = 4.80 Hz, = 8.48 Hz), 5.55 (s, 1H, NH (D2O exchangeable)), 6.55–7.75 (m, 13H, Ar-H), 8.15 (s, 1H, N=CH) 620
4a3426 (NH), 1704, 1617 (C=O), 1519 (C=N)1.18 (s, 1H, NH), 1.58 (s, 3H, acetyl CH3), 2.29 (s, 3H, CH3), 2.36 (s, 3H, CH3), 2.45 (s, 3H, C5–CH3), 3.63 (dd, 1H, [HA] CH2, J = 11.03 Hz), 3.73 (dd, 1H, [HB] CH2, J = 12.00 Hz), 4.24 (s, 6H, CH3), 5.51 (m, 1H, [HX] CH, = 4.40 Hz, = 11.00 Hz), 7.19–7.96 (m, 13H, Ar-H), 7.99 (s, 1H, C=NH)10.73, 12.63, 21.95, 44.51, 60.57, 107.83, 119.80, 126.39, 129.60, 129.06, 130.12, 130.82, 139.46, 142.53, 151.29, 154.32, 155.87, 169.21 586
4b3430 (NH), 1707, 1620 (C=O), 1594 (C=N)1.16 (s, 1H, NH), 2.00 (s, 3H, acetyl CH3), 2.31 (s, 3H, CH3), 2.40 (s, 3H, CH3), 2.50 (s, 3H, C5–CH3), 3.70 (dd, 1H, [HA] CH2, J = 12.03 Hz), 3.107 (dd, 1H, [HB] CH2, J = 11.00 Hz), 4.30 (s, 6H, CH3), 5.55 (m, 1H, [HX] CH, = 4.80 Hz, = 11.42 Hz), 7.25–8.00 (m, 12H, Ar-H), 8.05 (s, 1H, C=NH)10.56, 11.72, 21.44, 45.81, 60.51, 107.69, 119.03, 127.73, 29.72, 130.01, 131.12, 131.82, 139.92, 142.35, 150.58, 154.43, 155.62, 169.39 622 (M+), 624 (M+2)
4c3420 (NH), 1710, 1625 (C=O), 1593 (C=N)1.19 (s, 1H, NH), 2.05 (s, 3H, acetyl CH3), 2.34 (s, 3H, CH3), 2.43 (s, 3H, CH3), 2.52 (s, 3H, C5–CH3), 3.71 (dd, 1H, [HA] CH2, J = 14.03 Hz), 3.107 (dd, 1H, [HB] CH2, J = 12.05 Hz), 4.30 (s, 6H, CH3), 5.30 (m, 1H, [HX] CH, = 4.5 Hz, = 11.00 Hz), 7.30–7.12 (m, 12H, Ar-H) 8.00 (s, 1H, C=NH)9.13, 11.79, 21.69, 42.11, 59.48, 105.39, 117.51, 125.39, 127.16, 127.76, 128.23, 128.62, 137.03, 142.35, 150.48, 153.32, 154.69, 167.36 622 (M+), 624 (M+2)
4d3435 (NH), 1710, 1627 (C=O), 1560 (C=N)1.16 (s, 1H, NH), 2.07 (s, 3H, acetyl CH3), 2.32 (s, 3H, CH3), 2.42 (s, 3H, CH3), 2.51 (s, 3H, C5–CH3), 3.109 (dd, 1H, [HA] CH2, J = 11.03 Hz), 3.80 (dd, 1H, [HB] CH2, J = 12.00 Hz), 4.35 (s, 6H, CH3), 5.56 (m, 1H, [HX] CH, = 3.33 Hz, = 9.89 Hz), 7.24–8.05 (m, 12H, Ar-H) 8.10 (s, 1H, C=NH)8.79, 11.63, 22.41, 41.14, 58.44, 106. 43, 118.51, 124.82, 126.82, 127.62, 128.88, 128.96, 142.71, 151.51, 153.53, 154.46, 167.91 622 (M+), 624 (M+2)
4e3420 (NH), 1710, 1625 (C=O), 1593 (C=N)1.19 (s, 1H, NH), 2.05 (s, 3H, acetyl CH3), 2.30 (s, 3H, CH3), 2.43 (s, 3H, CH3), 2.47 (s, 3H, C5–CH3), 3.71 (dd, 1H, [HA] CH2, J = 14.03 Hz), 3.107 (dd, 1H, [HB] CH2, J = 13.05 Hz), 4.30 (s, 6H, CH3), 5.30 (m, 1H, [HX] CH, = 4.00 Hz, = 9 Hz), 7.30–7.92 (m, 12H, Ar-H), 7.99 (s, 1H, C=NH)9.12, 11.81, 22.59, 41.12, 58.91, 106.34, 118.51, 124.32, 126.93, 127.71, 128.42, 128.69, 143.01, 151.01, 153.35, 154.79, 167.66 602
4f3510 (OH), 3420 (NH), 1715, 1623 (C=O), 152 (C=N)1.71 (s, 1H, NH), 2.10 (s, 3H, acetyl CH3), 2.35 (s, 3H, CH3), 2.45 (s, 3H, CH3), 2.49 (s, 3H, C5–CH3), 3.71 (dd, 1H, [HA] CH2, J = 12.05 Hz), 3.108 (dd, 1H, [HB] CH2, J = 15.05 Hz), 4.35 (s, 6H, CH3), 5.32 (m, 1H, [HX] CH, = 4.43 Hz, = 8.50 Hz), 5.50 (s, 1H, OH), 7.35–7.1 (m, 12H, Ar-H), 8.11 (s, 1H, C=NH)9.15, 11.83, 22.58,14.12, 59.96, 107.39, 118.75, 125.39, 126.83, 127.91, 128.42, 128.84, 144.61, 151.48, 153.84, 154.86, 168.69 604
4g3437 (NH), 1708, 1627 (C=O), 1567 (C=N)1.67 (s, 1H, NH), 2.08 (s, 3H, acetyl CH3), 2.35 (s, 3H, CH3), 2.47 (s, 3H, CH3), 2.52 (s, 3H, C5–CH3), 3.73 (s, 3H, –OCH3), 3.80 (dd, 1H, [HA] CH2, J = 14.03 Hz), 3.2 (dd, 1H, [HB] CH2, J = 10.00 Hz), 4.37 (s, 6H, CH3), 5.56 (m, 1H, [HX] CH, = 4.00 Hz, = 11.00 Hz), 7.25–8.07 (m, 12H, Ar-H) 8.10 (s, 1H, C=NH)8.47, 12.38, 23.82, 42.85, 59.36, 106.28, 118.84, 126.92, 127.84, 128.47, 129.02, 129.96, 143.44, 151.86, 154.95, 155.79, 169.61 618