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574
Can. J. Chem. Vol. 85, 2007
Scheme 2.
C21H22N2O3 (%): C 71.98, H 6.33, N 7.99; found: C 72.01,
H 6.38, N 8.03.
Table 2. Comparative results for the synthesis of acridinediones
6a–6e.
Reaction
time
Yield
(%)
10-(4-Methoxybenzoylamino)-3,4,6,7,9,10-hexahydro-
1,8(2H,5H)acridinedione (3d)
5, 6
a
R′
Method
A
Solvent
Ethanol
2-Cl-C6H4
35 h
80
Pale brown solid; yield 81%; mp 228–230 °C. IR
(KBr, cm–1) 3471, 1654, 1614, 1585, 1388. 1H NMR
(90 MHz, CDCl3) δ: 2.01 (m, 4H, C3 and C6-CH2), 2.33 (m,
8H, C2, C4, C5, and C7- CH2), 3.11 (m, 2H, C9-CH2), 3.86 (s,
3H, OCH3), 7.01 (d, 2H, J = 8 Hz, Ar-H), 7.90 (d, 2H, J =
8 Hz, Ar-H). 13C NMR (50 MHz, CDCl3-DMSO-d6) δ: 18.7,
20.8, 24.53, 36.0, 55.6, 111.2, 114.2, 122.5, 129.7, 155.8,
163.4, 166.6, 197.7. MS m/z (%): 216 (0.32), 215 (1.9), 187
(9.8), 159 (3.2), 151 (8.1), 135 (29.6), 107 (9.4), 104 (10),
103 (16.8), 77 (76.5). Anal. calcd. for C21H22N2O4 (%): C
68.84, H 6.05, N 7.64; found: C 68.88, H 6.07, N 7.67.
B
C
A
Ethanol
—
Ethanol
5 min
17 min
32 h
85
93
81
b
c
2,4-Cl2-C6H3
2-CH3-C6H4
2-HO-C6H4
C6H5CH2
B
C
A
Ethanol
—
Ethanol
4 min
17 min
35 h
86
92
86
B
C
A
Ethanol
—
Ethanol
5 min
15 min
35 h
84
90
81
d
e
B
C
A
Ethanol
—
Ethanol
5 min
15 min
35 h
84
90
76
10-(2-Chlorobenzoylamino)-3,3,6,6-tetramethyl-
3,4,6,7,9,10-hexahydro-1,8(2H,5H)acridinedione (6a)
Yellow solid; yield 76%; mp 228–230 °C. IR (KBr, cm–1)
B
C
Ethanol
—
5 min
16 min
80
82
1
3410, 1680, 1640, 1550, 1380. H NMR (400 MHz, CDCl3-
DMSO-d6) δ: 1.05 and 1.08 (2s, 12H, gem-dimethyl), 2.18–
2.33 (2d, 4H, J = 16 Hz, C2 and C7-CH2), 2.33–2.48 (2d, 4H,
J = 16.6Hz, C4 and C5-CH2), 3.00–3.25 (2d, 2H, J = 20 Hz,
C9-CH2), 7.31–7.52 (m, 4H, ArH), 10.41 (s, 1H, NH). 13C
NMR (100.4 MHz, CDCl3-DMSO-d6) δ: 18.2, 28.1, 28.9,
31.7, 38.22, 49.5, 110.2, 125.7, 126.9, 129.0, 130.2, 131.0,
137.4, 152.1, 169.1, 196.4. MS m/z (%): 425 (M+, 1.5), 411
(2), 398 (2), 397 (3), 396 (19), 395 (20), 273 (32), 272 (37),
271 (40), 256 (1.1), 243 (21), 216 (19), 215 (100), 155 (36),
141 (20), 139 (61), 111 (24). Anal. calcd. for C24H27N2O3Cl
(%): C 67.51, H 6.37, N 6.56; found: C 67.65, H 6.47, N
6.69.
10-(4-Hydroxybenzoylamino)-3,4,6,7,9,10-hexahydro-
1,8(2H,5H)acridinedione (3b)
Pale yellow solid; yield 81%; mp 268–270 °C. IR
1
(KBr, cm–1) 3519, 3159, 1640, 1622, 1579, 1386. H NMR
(400 MHz, CDCl3-DMSO-d6) δ: 1.80–1.95 (m, 4H, C3 and
C6-CH2), 2.19–2.60 (m, 8H, C2, C4, C5, and C7- CH2), 2.85
and 2.98 (2d, 2H, J = 20 Hz, C9-CH2), 6.90 (d, 2H, J =
8 Hz, Ar-H), 7.80 (d, 2H, J = 8 Hz, Ar-H), 10.30 (br s, 1H,
Ar-OH), 11.00 (s, 1H, NH). MS m/z (%): 352 (M+, 15), 306
(2), 216 (6), 215 (8), 198 (4), 187 (97), 159 (16), 137 (34),
121 (51), 93 (18). Anal. calcd. for C20H20N2O4 (%): C
68.17, H 5.72, N 7.95; found: C 68.22, H 5.77, N 7.96.
10-(2,4-Dichlorobenzoylamino)-3,3,6,6-tetramethyl-
3,4,6,7,9,10-hexahydro-1,8(2H,5H)acridinedione (6b)
Yellow solid; yield 83%; mp 212–214 °C. IR (KBr, cm–1)
1
10-(4-Methylbenzoylamino)-3,4,6,7,9,10-hexahydro-
1,8(2H,5H)acridinedione (3c)
3440, 1700, 1640, 1590, 1390. H NMR (400 MHz, CDCl3-
DMSO-d6) δ: 1.07 and 1.12 (2s, 12H, gem-dimethyl), 2.19–
2.30 (2d, 4H, J = 16 Hz, C2 and C7-CH2), 2.35–2.49 (2d, 4H,
J = 16 Hz, C4 and C5-CH2), 3.11 (bs, 2H, C9-CH2), 7.43–
7.66 (m, 3H, Ar-H), 10.89 (s, 1H, NH). 13C NMR
(100.4 MHz, CDCl3-DMSO-d6) δ: 17.6, 27.2, 28.1, 31.1,
37.5, 48.9, 109.5, 126.8, 129.5, 129.6, 130.7, 131.7, 136.5,
151.5, 165.2, 195.7. MS m/z (%): 460 [(M+, 12), 462 (10),
464 (1)], 459 (2), 272 (92), 271 (50), 243 (2), 216 (20), 215
(100), 189 (21), 173 (47), 145 (16). Anal. calcd. for
C24H26N2O3Cl2 (%): C 62.50, H 5.63, N 6.07; found: C
62.24, H 5.89, N 6.09.
Greenish yellow solid; yield 86%; mp 148–150 °C. IR
(KBr, cm–1) 3450, 1681, 1624, 1577, 1384. 1H NMR
(90 MHz, CDCl3-DMSO-d6) δ: 1.80–2.10 (m, 7H, C3, C6-
CH2 and Ar-CH3), 2.20–2.40 (m, 8H, C2, C4, C5 and C7-
CH2), 3.00 (br s, 2H, C9-CH2), 7.30 (d, 2H, J = 8 Hz, Ar-H),
7.80 (d, 2H, J = 8 Hz, Ar-H), 9.50 (s, 1H, NH). 13C NMR
(100.4 MHz, CDCl3-DMSO-d6) δ: 18.3, 20.7, 21.3, 24.2,
35.8, 111.2, 127.5, 129.1, 154.3, 166.7, 196.5. MS m/z (%):
350 (M+, 18.3), 293 (6.1), 216 (100), 215 (97.9), 214 (90.4),
187 (93.5), 135 (51.8), 119 (100), 91 (73.4). Anal. calcd. for
© 2007 NRC Canada