Mol Divers
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1H, H4), 7.78 (t, J = 7.5 Hz, 1H, H6), 7.67 (dd, J = 8.8,
1.8 Hz, 1H, H3), 7.32 (t, J = 7.5 Hz, 1H, H7), 7.25 (d,
H2, H7), 6.56 (s, 2H, H2 , H6 ), 5.81 (s, 2H, CH2), 5.45 (s,
2H, CH2), 3.70 (s, 6H, OCH3), 3.69 (s, 3H, OCH3). Anal.
Calcd for C26H24N4O4: C, 68.41; H, 5.30; N, 12.27. Found:
C, 68.59; H, 5.18; N, 12.13.
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J = 7.7Hz, 2H, H2 , H6 ), 6.86(d, J = 7.7Hz, 2H, H3 , H5 ),
5.75 (s, 2H, CH2), 5.45 (s, 2H, CH2), 3.72 (s, 3H, OCH3),
2.73 (q, J = 7.5 Hz, 2H, CH2), 1.30 (t, J = 7.5 Hz, 3H,
CH3).13C NMR (125 MHz, DMSO-d6): 176.4, 159.1, 142.8,
141.6, 140.1, 136.9, 134.4, 133.9, 131.2, 129.5, 127.8, 126.6,
124.5, 123.0, 121.6, 121.2, 116.4, 116.1, 114.0, 55.1, 52.3,
41.5, 27.3, 15.5. Anal. Calcd for C26H24N4O2: C, 73.56; H,
5.70; N, 13.20. Found: C, 73.74; H, 5.58; N, 13.03.
2-Chloro-10-((1-(3,4,5-trimethoxybenzyl)-1H-1,2,3-triazol-
4-yl)methyl)acridin-9(10H)-one (8i)
Yellow crystals; yield: 63 %, mp 244–245 ◦C. IR (KBr):
3114, 2953, 1787, 16031, 1594 cm−1. 1H NMR (500 MHz,
DMSO-d6): 8.35 (d, J = 7.5 Hz, 1H, H8), 8.26 (d, J =
2.3 Hz, 1H, H1), 8.22 (s, 1H, triazole), 8.01 (d, J = 9.0 Hz,
1H, H3), 7.96 (d, J = 9.0 Hz, 1H, H4), 7.83 (m, 2H, H5, H6),
4-Fluoro-10-((1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-
yl)methyl)acridin-9(10H)-one (8f)
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7.37 (t, J = 7.5 Hz, 1H, H7), 6.56 (s, 2H, H2 , H6 ), 5.82 (s,
2H, CH2), 5.45 (s, 2H, CH2), 3.66 (s, 6H, OCH3), 3.61(s,
3H, OCH3). 13C NMR (125 MHz, DMSO-d6): 175.6, 152.9,
142.5, 141.6, 140.4, 137.2, 134.5, 133.8, 131.3, 126.5, 126.1,
125.2, 123.5, 122.6, 121.9, 121.6, 119.1, 116.4, 105.3, 59.9,
55.7, 53.0, 41.7. Anal. Calcd for C26H23ClN4O4: C, 63.61;
H, 4.72; N, 11.41. Found: C, 63.77; H, 4.58; N, 11.58.
White crystals; yield: 71 %, mp 132–133 ◦C. IR (KBr):
1
3150, 2937, 1738, 1638, 1608 cm−1. H NMR (500 MHz,
DMSO-d6): 8.29 (d, J = 7.3 Hz, 1H, H8), 8.18–8.16
(m, 2H, H1, triazole), 7.81–7.76 (m, 2H, H5, H6), 7.67
(ddd, J = 15.2, 7.6, 1.3‘Hz, 1H, H3), 7.36–7.29 (m, 2H,
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H2, H7), 7.24 (d, J = 8.6 Hz, 2H, H2 , H6 ), 6.89 (d,
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J = 8.6 Hz, 2H, H3 , H5 ), 5.69 (s, 2H, CH2), 5.47(s,
2H, CH2), 3.66 (s, 3H, OCH3). 13C NMR (125 MHz,
DMSO-d6): 176.0, 159.0, 151.3 (d, JC−F = 243.9 Hz),
144.2, 143.5, 134.5, 132.2, 129.4, 127.8, 126.4, 124.9,
122.9, 122.7, 122.2, 121.9 (d, JC−F = 7.6 Hz), 121.8,
121.1 (d, JC−F = 23.4 Hz), 116.6, 114.0, 55.1, 52.3, 47.1
(d, JC−F = 14.8 Hz). Anal. Calcd for C24H19F N4O2: C,
69.55; H, 4.62; N, 13.52. Found: C, 69.73; H, 4.51; N,
13.35.
2-Methoxy-10-((1-(3,4,5-trimethoxybenzyl)-1H-1,2,3-
triazol-4-yl)methyl)acridin-9(10H)-one (8j)
Yellow crystals; yield: 64 %, mp 193–194 ◦C. IR (KBr):
3112, 2931, 1735, 1631, 1594 cm−1. H NMR (500 MHz,
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DMSO-d6): 8.36 (d, J = 7.5 Hz, 1H, H8), 8.19 (s, 1H, tri-
azole), 7.96–7.93 (m, 2H, H4, H5), 7.79–7.77 (m, 2H, H1,
H6), 7.46 (dd, J = 9.2, 3.0 Hz, 1H, H3), 7.32 (t, J = 7.5 Hz,
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1H, H7), 6.59 (s, 2H, H2 , H6 ), 5.82 (s, 2H, CH2), 5.44 (s,
2H, CH2), 3.88 (s, 3H, OCH3), 3.65 (s, 6H, OCH3), 3.61
(s, 3H, OCH3). 13C NMR (125 MHz, DMSO-d6): 176.0,
154.1, 152.9, 142.8, 141.3, 137.1, 136.5, 133.8, 131.4, 126.6,
123.9, 123.4, 122.4, 121.1, 120.9, 118.3, 116.1, 106.2, 105.2,
59.9, 55.7, 55.4, 52.9, 41.6. Anal. Calcd for C27H26N4O5: C,
66.66; H, 5.39; N, 11.52. Found: C, 66.83; H, 5.21; N, 11.35.
4-Methoxy-10-((1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-
yl)methyl)acridin-9(10H)-one (8g)
Pale yellow crystals; yield: 69 %, mp 134–135 ◦C. IR (KBr):
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3120, 2922, 1735, 1629, 1598 cm−1. H NMR (500 MHz,
DMSO-d6): 8.24 (dd, J = 8.0, 1.4 Hz, 1H, H8), 8.03 (s,
1H, triazole), 7.92 (dd, J = 7.6, 1.0 Hz, 1H, H1), 7.79–
7.72 (m, 2H, H5, H6), 7.43 (dd, J = 7.6, 1.0 Hz, 1H,
H3), 7.32–7.29 (m, 2H, H2, H7), 7.18 (d, J = 7.8 Hz,
2-Bromo-10-((1-(3,4,5-trimethoxybenzyl)-1H-1,2,3-triazol-
4-yl)methyl)acridin-9(10H)-one (8k)
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2H, H2 , H6 ), 6.80 (d, J = 7.8 Hz, 2H, H3 , H5 ), 5.73
(s, 2H, CH2), 5.51 (s, 2H, CH2), 3.75 (s, 3H, OCH3),
3.69 (s, 3H, OCH3). Anal. Calcd for C25H22N4O3: C,
70.41; H, 5.20; N, 13.14. Found: C, 70.68; H, 5.04; N,
12.94.
Pale yellow crystals; yield: 62 %, mp 246–248 ◦C . IR (KBr):
3115, 2931, 1751, 1627, 1595 cm−1. H NMR (500 MHz,
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DMSO-d6): 8.41 (s, 1H, H1), 8.35 (d, J = 7.8 Hz, 1H, H8),
8.22 (s, 1H, triazole), 7.97–7.95 (m, 3H, H3, H4, H5), 7.84–
7.81 (t, J = 7.8 Hz, 1H, H6), 7.38 (t, J = 7.8 Hz, 1H, H7),
10-((1-(3,4,5-Trimethoxybenzyl)-1H-1,2,3-triazol-4-
yl)methyl)acridin-9(10H)-one (8h)
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6.56 (s, 2H, H2 , H6 ), 5.82 (s, 2H, CH2), 5.44 (s, 2H, CH2),
3.66 (s, 6H, OCH3), 3.61 (s, 3H, OCH3). MS m/z (%) 537
([M+. + 2], 10), 535 (M+.10), 534 (29), 274 (13), 244 (25),
228 (32), 203 (19), 181 (100), 165 (27), 148 (29), 135 (26),
121 (50), 106 (94), 91 (51), 77 (46), 51 (23). Anal. Calcd
for C26H23 Br N4O4: C, 58.33; H, 4.33; N, 10.46. Found: C,
58.51; H, 4.18; N, 10.29.
White crystals; yield: 68 %, mp 232–234 ◦C . IR (KBr): 3114,
2937, 1745, 1631, 1603 cm−1. 1H NMR (500 MHz, DMSO-
d6): 8.24 (dd, J = 7.5 Hz, 1.3 Hz, 2H, H1, H8), 8.22 (s, 1H,
triazole), 7.94 (d, J = 7.5 Hz, 2H, H4, H5), 7.82–7.78 (t,
J = 7.5 Hz, 2H, 2H, H3, H6), 7.35 (t, J = 7.5 Hz, 2H,
123