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NCH2), 3.84 (s, 3H, OCH3), 1.98 (m, 2H, CH2), 1.37 (m, 2H, CH2), 1H, J ¼ 1 Hz), 8.25 (d, 1H, J ¼ 9 Hz), 7.80 (dd, 1H, J ¼ 10/2 Hz),
0.95 (t, 3H, CH3). 13C NMR (100 MHz, DMSO-d6): d (ppm) 7.75 (dd, 1H, J ¼ 10/3 Hz), 7.68 (d, 1H, J ¼ 9 Hz), 6.69 (d, 1H, J ¼
159.47, 147.13, 146.49, 139.23, 132.10, 130.77, 130.05, 129.65, 3 Hz), 4.46 (t, 2H, NCH2), 3.89 (s, 3H, OCH3), 2.02 (m, 2H, CH2),
126.99, 125.62, 124.54, 123.39, 122.45, 121.94, 121.95, 97.79, 1.42 (m, 2H, CH2), 0.99 (t, 3H, CH3). 13C NMR (100 MHz, DMSO-
56.40, 50.05, 31.39, 19.49, 13.93. Anal. calcd for C21H22ClN3O: C d6): d (ppm) 159.47, 147.30, 146.99, 139.23, 135.49, 134.10,
68.56, H 6.03, N 11.42%; found: C 68.62, H 6.08, N 11.32%. 131.99, 130.15, 128.23, 127.71, 125.59, 124.59, 124.49, 123.60,
HRMS (ESI+) m/z calcd for C21H22N3O [M ꢁ Cl]+: 332.1763 121.13, 98.00, 56.48, 50.10, 31.36, 19.50, 13.92. Anal. calcd for
(100%), 333.1796 (23%); found: 332.1790 (100%), 333.1803
(37%).
C21H21Cl2N3O: C 62.69, H 5.26, N 10.44%; found: C 62.51, H
5.25, N 10.31%. HRMS (ESI+) m/z calcd for C21H21ClN3O [M ꢁ
Cl]+: 366.1373 (100%), 367.1407 (23%), 368.1344 (35%),
369.1378 (8%); found: 366.1418 (100%), 367.1409 (53%),
368.1361 (66%), 369.1374 (19%).
1-(6-Chloro-2-methoxyacridin-9-yl)-3-methylimidazolium
chloride (10)
1-Methylimidazole (441 mg, 5.4 mmol) and 3c (1.31 g, 4.7
mmol) were reacted according to general procedure A to give 10
(1.44 g, 85%) as greenish solid. Mp 240–245 ꢀC. FTIR: n
1-(6-Chloro-2-methoxyacridin-9-yl)-3-octylimidazolium
chloride (13)
(ATR, cmꢁ1) 3053 (C–H), 1631 (C]N), 1564, 1476, 1423 (C]C), 1-Octylimidazole (324 mg, 1.8 mmol) and 3c (439 mg, 1.6 mmol)
1216 (C–O), 832 (C–Cl). 1H NMR (400 MHz, DMSO-d6): d (ppm) were reacted according to general method A to give 13 (545 mg,
9.77 (bs, 1H, NCHN), 8.35 (dd z bd, 2H, J ¼ 5 Hz), 8.27 (bs, 1H), 75%) as yellow solid. Mp 320–330 ꢀC. FTIR: n (ATR, cmꢁ1) 3069,
8.22 (d, 1H, J ¼ 9 Hz), 7.75 (dd, 1H, J ¼ 9/3 Hz), 7.71–7.67 (m, 2954, 2924, 2854 (C–H), 1631 (C]N), 1595, 1561, 1476 (C]C),
2H), 6.80 (d, 1H, J ¼ 3 Hz), 4.07 (s, 3H, NCH3), 3.86 (s, 3H, 1281, 1233, 1154, 1030 (C–O), 818, 747 (C–Cl). 1H NMR (400
OCH3). 13C NMR (100 MHz, DMSO-d6): d(ppm) 159.67, 147.30, MHz, DMSO-d6): d (ppm) 9.86 (s, 1H, NCHN), 8.33 (bs, 1H), 8.31
146.93, 139.38, 135.93, 135.43, 134.17, 131.89, 129.98, 128.14, (s, 1H), 8.28 (d, 1H, J ¼ 10 Hz), 7.95 (dt, 1H, Jt ¼ 7 Hz, Jd ¼ 2 Hz),
127.66, 125.47, 124.59, 123.67, 121.24, 98.35, 56.69, 37.24. Anal. 7.77 (dt, 1H, Jt ¼ 7 Hz, Jd ¼ 1 Hz), 7.71 (dd, 1H, J ¼ 9/3 Hz), 7.56
calcd for C18H15Cl2N3O: C 60.01, H 4.20, N 11.66%; found: C (d, 1H, J ¼ 9 Hz), 6.69 (d, 1H, J ¼ 3 Hz), 4.42 (t, 2H, NCH2), 3.87
59.98,
C
H 4.35, N
11.61%. HRMS (ESI+) m/z calcd for (s, 3H, OCH3), 2.00 (m, 2H, CH2), 1.36–1.26 (m, 10H, CH2), 0.85
18H15ClN3O [MꢁCl]+: 324.0904 (100%), 325.0937 (20%), (t, 3H, CH3). 13C NMR (100 MHz, DMSO-d6): d (ppm) 159.47,
326.0875 (34%), 327.0908 (7%); found: 324.0898 (100%), 147.14, 146.50, 139.22, 133.58, 132.11, 130.76, 130.08, 129.61,
325.0938 (35%), 326.0886 (52%), 327.0906 (10%).
126.96, 125.62, 124.53, 123.40, 122.47, 121.91, 97.86, 56.39,
50.32, 31.70, 29.39, 29.07, 28.91, 26.15, 22.62, 14.49. Anal. calcd
for C25H29Cl2N3O: C 65.50, H 6.38, N 9.17%; found: C 65.52, H
6.35, N 9.19%. HRMS (ESI+) m/z calcd for C25H29ClN3O [M ꢁ
Cl]+: 422.1999 (100%), 423.2033 (28%), 424.1970 (34%),
425.2004 (10%); found: 422.1992 (100%), 423.2543 (%),
424.1968 (46%).
1-(6-Chloro-2-methoxyacridin-9-yl)-3-ethylimidazolium
chloride (11)
1-Ethylimidazole (519 mg, 5.4 mmol) and 3c (1.3 g, 4.7 mmol)
were reacted according to general method A to give 11 (1.41 g,
81%) as greenish solid. Mp 214–216 ꢀC. FTIR: n (ATR, cmꢁ1
)
3053, 2988 (C–H), 1629 (C]N), 1547, 1432, 1408 (C]C), 1268,
1140 (C–O), 758 (C–Cl). 1H NMR (400 MHz, DMSO-d6): d (ppm)
1-(Acridin-9-yl)-3-(4-methylbenzyl)-imidazolium chloride (14)
9.88 (s, 1H, NCHN), 8.35 (d, 2H, J ¼ 2 Hz), 8.30 (bs, 1H), 8.27 (d, 1-(4-Methylbenzyl)-imidazole (310 mg, 1.8 mmol) and 3a
2H, 10 Hz), 7.78–7.66 (m, 3H), 6.73 (d, 1H, 2 Hz), 4.42 (t, 2H, (337 mg, 1.6 mmol) were reacted according to general method A
NCH2), 3.86 (s, 3H, OCH3), 1.60 (t, 3H, CH3). 13C NMR (100 MHz, to give 14 (520 mg, 85%) as white solid. Mp 205–210 ꢀC. FTIR: n
DMSO-d6): d (ppm) 159.69, 147.32, 146.98, 138.98, 135.46, (ATR, cmꢁ1) 3020, 2946 (C–H), 1626 (C]N), 1536, 1520, 1439
134.72, 131.94, 130.07, 128.18, 127.66, 125.40, 124.66, 124.33, (C]C), 1259, 1132 (C–C), 770 (C–Cl). 1H NMR (400 MHz, DMSO-
123.63, 121.19, 98.36, 56.62, 45.80, 15.02. Anal. calcd for d6): d (ppm) 9.95 (s, 1H, NCHN), 8.34–8.28 (m, 4H), 7.99 (bt, 2H,
C
19H17Cl2N3O: C 60.97, H 4.58, N 11.23%; found: C 60.93, H J ¼ 8 Hz), 7.77 (dt, 2H, Jt ¼ 6 Hz, Jd ¼ 1 Hz), 7.60 (d, 2H, J ¼ 9 Hz),
4.55, N 11.30%. HRMS (ESI+) m/z calcd for C19H17ClN3O [M ꢁ 7.48 (d, 2H, J ¼ 8 Hz), 7.27 (d, 2H, J ¼ 8 Hz), 5.59 (s, 2H), 2.30 (s,
Cl]+: 338.1060 (100%), 339.1094 (21%), 340.1031 (34%), CH3). 13C NMR (100 MHz, DMSO-d6): d (ppm) 149.06, 139.46,
341.1065 (7%); found: 338.1064 (100%), 339.1095 (44%), 139.04, 136.02, 132.05, 131.65, 130.25, 130.01, 129.57, 129.39,
340.1045 (56%), 341.1062 (10%).
126.18, 124.39, 122.51, 122.08, 53.26, 21.32. Anal. calcd for
C
24H20ClN3: C 74.70, H 5.22, N 10.89%; found: C 74.80, H
1-(6-Chloro-2-methoxyacridin-9-yl)-3-butylimidazolium
chloride (12)
5.20, N 10.90%. HRMS (ESI+) m/z calcd for C24H20N3 [M ꢁ Cl]+:
350.1657 (100%), 351.1691 (27%); found: 350.1650 (100%),
351.1682 (74%).
1-Butylimidazole (672 mg, 5.4 mmol) and 3c (1.3 g, 4.7 mmol)
were reacted according to general method A to give 12 (1.52 g,
1-(Acridin-9-yl)-3-(4-bromobenzyl)-imidazolium bromide (15)
80%) as greenish solid. Mp 220–225 ꢀC. FTIR: n (ATR, cmꢁ1
)
3079, 2956 (C–H), 1631 (C]N), 1542, 1480, 1426 (C]C), 1238, 4-Bromobenzyl bromide (748 mg, 3.0 mmol) and 6a (244 mg, 1.0
1127 (C–O), 830 (C–Cl). 1H NMR (400 MHz, DMSO-d6): d (ppm) mmol) were reacted according to general method B to give 15
10.00 (s, 1H, NCHN), 8.42 (bs, 1H), 8.38 (d, 1H, J ¼ 2 Hz), 8.33 (d, (445 mg, 90%) as yellow solid. Mp 280–290 ꢀC. FTIR: n
39000 | RSC Adv., 2018, 8, 38995–39004
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