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. 2020 Oct 29;25(21):5013. doi: 10.3390/molecules25215013
graphic file with name molecules-25-05013-i001.jpg 1. White solid (69%), mp 118 °C. 1H NMR (300 MHz, DMSO-d6) δ 10.46 (s, 1H, NH), 7.85 (s, 1H, CH), 7.66 (d, J = 8.4 Hz, 2H, arom), 7.43 (d, J = 8.4 Hz, 2H, arom), 7.23 (t, J = 7.7 Hz, 2H, arom), 7.09 (d, J = 7.9 Hz, 2H, arom), 6.76 (t, J = 7.2 Hz, 1H, arom). 13C NMR (75 MHz, DMSO-d6) δ 145.5, 135.4, 135.2, 132.5, 129.5, 129.1, 127.5, 119.41, 112.5.
graphic file with name molecules-25-05013-i002.jpg 2. White solid (92%), mp 151 °C. 1H NMR (300 MHz, DMSO-d6) δ 10.33 (s, 1H, NH), 7.80 (s, 1H, CH), 7.66 (s, 1H, arom), 7.42 (d, J = 8.4 Hz, 2H, arom), 7.00 (q, J = 8.4 Hz, 5H, arom), 2.09 (s, 3H, CH3). 13C NMR (75 MHz, DMSO-d6) δ 138.6, 130.8, 130.1, 127.7, 125.4, 124.5, 123.3, 122.8, 107.92, 16.1.
graphic file with name molecules-25-05013-i003.jpg 3. White solid (87%), mp 141 °C. 1H NMR (300 MHz, DMSO-d6) δ 10.24 (s, 1H, NH), 7.78 (s, 1H, CH), 7.63 (d, J = 8.5 Hz, 2H, arom), 7.41 (d, J = 8.5 Hz, 2H, arom), 7.01 (d, J = 8.9 Hz, 2H, arom), 6.84 (d, J = 8.9 Hz, 2H, arom), 3.69 (s, 3H, OCH3). 13C NMR (75 MHz, DMSO-d6) δ 153.2, 139.5, 135.5, 134.2, 132.1, 129.0, 127.3, 115.0, 113.5, 55.7.
graphic file with name molecules-25-05013-i004.jpg 4. White solid (77%), mp 135 °C. 1H NMR (300 MHz, DMSO-d6) δ 7.02 (d, 2H, J = 6.0 Hz), 7.22 (t, 2H, J = 9.1 Hz), 7.37 (d, 2H, J = 9.1 Hz), 7.68–7.73(m, 2H), 7.87(s, 1H), 10.49 (s, 1H). 13C NMR (75 MHz, DMSO-d6) δ 114.3, 115.9, 116.2, 128.0, 132.1, 132,63, 136,7, 145.0, 109.9.
graphic file with name molecules-25-05013-i005.jpg 5. White solid (76%), mp 153 °C. 1H NMR (300 MHz, DMSO-d6) δ 10.58 (s, 1H, NH), 7.85 (s, 1H, CH), 7.67 (d, J = 8.3 Hz, 2H, arom), 7.48–7.38 (m, 2H, arom), 7.25 (d, J = 8.7 Hz, 2H, arom), 7.07 (d, J = 8.7 Hz, 2H, arom). 13C NMR (75 MHz, DMSO-d6) δ 144.4, 136.3, 135.0, 132.8, 129.3, 129.1, 127.7, 122.6, 113.9.
graphic file with name molecules-25-05013-i006.jpg 6. White solid (94%), mp 131 °C. 1H NMR (300 MHz, DMSO-d6) δ 10.59 (s, 1H, NH), 7.85 (s, 1H, CH), 7.67 (d, J = 8.5 Hz, 2H, arom), 7.43 (d, J = 8.5 Hz, 2H, arom), 7.37 (d, J = 8.8 Hz, 2H, arom), 7.03 (d, J = 8.8 Hz, 2H, arom). 13C NMR (75 MHz, DMSO-d6) δ 144.8, 136.4, 134.9, 132.8, 132.2, 129.1, 127.7, 114.4, 110.2, 39.9.
graphic file with name molecules-25-05013-i007.jpg 7. White solid (72%), mp 119 °C. 1H NMR (300 MHz, DMSO-d6) δ 10.30 (s, 1H, NH), 7.81 (s, 1H, CH), 7.65 (d, J = 8.5 Hz, 2H, arom), 7.42 (d, J = 8.5 Hz, 2H, arom), 6.69 (s, 2H, arom), 6.41 (s, 1H, arom), 2.22 (s, 6H, CH3). 13C NMR (75 MHz, DMSO-d6) δ 145.3, 138.5, 135.3, 135.0, 132.3, 129.1, 127.5, 121.3, 110.3, 21.7.
graphic file with name molecules-25-05013-i008.jpg 8. White solid (88%), mp 114 °C. 1H NMR (300 MHz, DMSO-d6) δ 10.16 (s, 1H, NH), 8.28 (s, 1H, CH), 7.69 (d, J = 8.7 Hz, 2H, arom), 7.56 (d, J = 8.7 Hz, 1H, arom), 7.51–7.43 (m, 3H, arom), 7.35–7.17 (m, 1H, arom). 13C NMR (75 MHz, DMSO-d6) δ 162.3, 140.9, 140.1, 134.6, 133.4, 129.2, 129.0, 128.5, 128.1, 122.8, 117.1, 115.5.
graphic file with name molecules-25-05013-i009.jpg 9. White solid (92%), mp 112 °C. 1H NMR (300 MHz, DMSO-d6) δ 10.74 (s, 1H, NH), 7.90 (d, J = 14.3 Hz, 1H), 7.69 (d, J = 8.3 Hz, 2H, arom), 7.44 (q, J = 8.3, 7.5 Hz, 3H, arom), 7.26 (s, 1H, CH), 7.00 (d, J = 8.4 Hz, 1H, arom). 13C NMR (75 MHz, DMSO-d6) δ 145.6, 137.6, 134.6, 133.2, 132.1, 131.5, 131.3, 130.2, 129.8, 129.1, 128.0, 120.1, 113.3, 112.8.