I. Cikotiene et al. / Tetrahedron 67 (2011) 706e717
715
36 have been deposited at the Cambridge Crystallographic Data
Centre (CCDC number 703429).
127.8, 128.0, 129.5, 132.2 (q, J¼35.75 Hz), 139.7, 140.2, 145.7, 153.1,
157.9, 158.5167.7, 171.8 ppm. Anal. Calcd for C27H23F3N4O3: C, 63.77;
H, 4.56; N, 11.02. Found: C, 63.89; H, 4.62; N, 10.95.
4.4.7. 6-Methoxycarbonyl-2-methylthio-4-morpholino-7-phenyl-
4.4.12. 2-Methoxycarbonylacridine 42. Yellowish crystals, yield 76%
mp 82e83 ꢂC. IR (KBr): nmax¼1732 (C]O) cmꢃ1. 1H NMR (300 MHz,
quinazoline 37. White crystals, yield 90% mp 154e156 ꢂC (from
octane). IR (KBr): nmax¼1717 (C]O) cmꢃ1
.
1H NMR (300 MHz,
¼2.64 (3H, s, SCH3), 3.68 (3H, s, OCH3), 3.93 (8H, s, N
CDCl3):
d
¼4.00 (3H, s, OCH3), 7.57 (1H, ddd, J¼8.1, 7.2, 1.5 Hz, ArH),
CDCl3):
d
7.85 (1H, ddd, J¼8.4, 7.2, 1.5 Hz, ArH), 8.04 (1H, dd, J¼8,4, 0.6 Hz,
C3eH), 8.27e8.32 (3H, m, ArH) 8.79 (1H, d, J¼0.6 Hz, C1eH), 8.92
(CH2)4O), 7.39e7.45 (5H, m, ArH), 7.74 (1H, s, CH), 8.37 (1H, s, CH)
ppm. 13C NMR (75 Hz, CDCl3):
d¼14.2, 49.9, 52.2, 66.6, 112.0, 126.3,
(1H, s, C9eH) ppm. 13C NMR (75 Hz, CDCl3):
126.8, 127.4, 128.5, 128.9, 129.2, 129.5, 131.9, 132.2, 138.8, 149.4,
166.5, 169.8 ppm. Anal. Calcd for C15H11NO2: C, 75.94; H, 4.67; N,
5.90. Found: C, 76.00; H, 4.65; N, 6.00.
d
¼52.6, 125.3, 126.4,
127.7, 128.0, 128.1, 128.4, 128.8, 140.3, 146.2, 153.9, 163.1, 168.1,
169.7 ppm. Anal. Calcd for C21H21N3O3S: C, 63.78; H, 5.35; N, 10.63.
Found: C, 63.75; H, 5.34; N, 10.77.
4.4.8. 4-(3-Bromomethylanilino)-6-methoxycarbonyl-7-phenyl-2-
(2-propenylamino)quinazoline 38. White crystals, yield 65% mp
215e217 ꢂC (from methanol). IR (KBr): nmax¼3370, 3079 (NH), 1706
4.4.13. 2-Methoxycarbonyl-3-phenylacridine 43. Yellow crystals,
yield 90%, mp 156e157 ꢂC (from MeOH). IR (KBr): nmax 1724 (C]O)
cmꢃ1. 1H NMR (300 MHz, CDCl3):
d¼3.94 (3H, s, OCH3); 7.37 (1H, t,
(C]O) cmꢃ1. 1H NMR (300 MHz, CDCl3):
d¼2.61 (1H, br s, NH), 3.67
J¼7.5 Hz, ArH), 7.47e7.58 (3H, m, ArH), 7.70 (1H, s, C(9)eH),
7.72e7.78 (3H, m, ArH), 7.82 (1H, d, J¼8.7 Hz, ArH), 8.00 (1H, s, C
(1)eH), 8.12 (1H, d, J¼8.7 Hz, ArH), 8.16 (1H, s, C(4)eH). 13C NMR
(3H, s, OCH3), 4.17e4.20 (2H, m, CH2), 5.20 (1H, dd, J¼10.2,1.2 Hz, ]
CH), 5.32 (1H, dd, J¼17.1, 1.2 Hz, ]CH), 5.98e6.10 (1H, m, ]CH),
7.27e7.35 (5H, m, ArH), 7.40e7.46 (3H, m, ArH), 7.41 (1H, s, CH), 7.61
(1H, d, J¼7.5 Hz, ArH), 8.19 (1H, br s, NH), 8.39 (1H, s, CH) ppm. 13C
(75 Hz, CDCl3):
d
¼52.9, 124.5, 126.0, 126.7, 127.3, 127.7, 127.8, 128.0,
128.3, 128.7, 129.6, 129.7, 129.8, 130.2, 130.8, 135.8, 137.4, 149.0,
149.2, 163.7 ppm. Anal. Calcd for C21H15NO2: C, 80.49; H, 4.82; N,
4.47. Found: C, 80.54; H, 4.92; N, 4.41.
NMR (75 Hz, CDCl3):
d
¼43.9, 52.0, 116.0, 119.8, 122.5, 123.8, 124.5,
124.9,127.2,127.6,127.9,128.1,128.4,129.0,130.1,134.8,139.4,140.7,
147.2,157.9,159.7,161.4,168.3 ppm. Anal. Calcd for C25H21BrN4O2: C,
61.36; H, 4.33; N, 11.45. Found: C, 61.58; H, 4.31; N, 11.55.
4.4.14. 2-Methoxycarbonyl-7-methoxy-3-phenylacridine
44. Brownish crystals, yield 75% mp 122e123 ꢂC. IR (KBr):
nmax¼1726 (C]O) cmꢃ1. 1H NMR (300 MHz, CDCl3):
¼3.75 (3H, s,
d
4.4.9. 6-Methoxycarbonyl-7-phenyl-2-(2-propenylamino)-4-(3-tri-
fluoromethylanilino)-quinazoline 39. White crystals, yield 71% mp
229e230 ꢂC (from methanol). IR (KBr): nmax¼3362, 3076 (NH),
OCH3), 4.03 (3H, s, OCH3), 7.23 (1H, d, J¼2.7 Hz, C8eH), 7.43e7.50
(5H, m, ArH), 7.57 (1H, dd, J¼9.4, 2.7 Hz, ArH), 8.23 (1H, d, J¼9.4 Hz,
ArH), 8.29 (1H, s, C1eH), 8.54 (1H, s, C9eH), 8.77 (1H, s, C4eH) ppm.
1700 (C]O) cmꢃ1
.
1H NMR (300 MHz, DMSO-d6):
d
¼3.62 (3H, s,
13C NMR (75 Hz, CDCl3):
127.6,128.2,128.3,129.7,129.9,130.0,131.1,135.6,140.5,142.1,146.4,
146.6,157.5,168.6 ppm. Anal. Calcd for C22H17NO3: C, 76.95; H, 4.99;
N, 4.08. Found: C, 77.00; H, 5.04; N, 3.99.
d
¼52.2, 56.6, 103.2, 124.7, 127.3, 127.6,
OCH3), 4.01e4.03 (2H, m, CH2), 5.07 (1H, dd, J¼10.2, 1.2 Hz, ]CH),
5.19 (1H, dd, J¼17.1, 1.2 Hz, ]CH), 5.92e6.02 (1H, m, ]CH),
7.35e7.46 (7H, m, ArH), 7.24 (1H, s, CH), 7.62 (1H, t, J¼8.1 Hz,
ArH), 8.18 (1H, br s, NH), 8.51e8.62 (1H, m, ArH), 8.88 (1H, s, CH),
10.08 (1H, br s, NH) ppm. 13C NMR (75 Hz, DMSO-d6):
d¼43.0,
51.7, 109.6, 119.4 (q, J¼3 Hz), 122.4, 122.9, 125.2, 125.9, 126.6 (q,
J¼3 Hz), 127.4, 127.8, 128.1, 128.9, 129.3, 129.4, 130.2 (q, J¼38.0 Hz),
135.9, 140.2, 140.4, 145.5, 145.6, 153.7, 167.8, 171.9 ppm. Anal. Calcd
for C26H21F3N4O2: C, 65.27; H, 4.42; N, 11.71. Found: C, 65.33; H,
4.39; N, 11.66.
4.4.15. 7-Ethoxy-2-methoxycarbonyl-3-phenylacridine
45. Brownish crystals, yield 51% mp 120e121 ꢂC. IR (KBr):
nmax¼1724 (C]O) cmꢃ1. 1H NMR (300 MHz, CDCl3):
¼1.53 (3H, t,
d
J¼6.9 Hz, OCH2CH3), 3.77 (3H, s, OCH3), 4.19 (3H, q, J¼6.9 Hz,
OCH2CH3), 7.13 (1H, d, J¼2.7 Hz, C8eH), 7.41e7.52 (6H, m, ArH), 8.12
(1H, d, J¼9.6 Hz, ArH), 8.21(1H, s, C1eH), 8.48 (1H, s, C9eH), 8.64 (1H,
s, C4eH) ppm. 13C NMR (75 Hz, CDCl3):
125.0,127.3,128.2,128.4,128.6,129.9,130.8,130.9,131.4,134.9,141.0,
141.7,147.4,147.7,156.9,168.9,170.0 ppm. Anal. Calcd for C23H19NO3:
C, 77.29; H, 5.36; N, 3.92. Found: C, 77.33; H, 5.19; N, 3.95.
d
¼14.9, 52.8, 64.2, 104.0,
4.4.10. Methyl (Z)-2-[5-formyl-2-morpholino-6-(3-trifluoromethyl-
anilino)-4-pyrimidinyl-1-phenyl-ethenyl]thioacetate
40. Yellow
ꢂ
crystals, yield 48% mp 181e182 C (from methanol). IR (KBr):
nmax¼3369 (NH),1723,1641 (C]O) cmꢃ1. 1H NMR (300 MHz, CDCl3):
d
¼3.14e3.18 and 3.38e3.41 (4H, 2 m, N(CH2)2), 3.54 (2H, s, SCH2),
3.64e3.66 and 3.74e3.75 (4H, 2 m, O(CH2)2), 3.79 (3H, s, OCH3), 7.06
(1H, s, CH), 7.31e7.36 (6H, m, ArH), 7.45 (1H, t, J¼8.4 Hz, ArH), 7.54
(1H, d, J¼8.1 Hz, ArH), 8.36 (1H, br s, ArH), 10.16 (1H, s, CHO), 11.40
4.4.16. 3-Methoxycarbonyl-2-phenyl-9H-carbazole
46. Yellowish
crystals, yield 80% mp 165e167 ꢂC. IR (KBr): nmax¼3388 (NH), 1732
(C]O) cmꢃ1
.
1H NMR (300 MHz, CDCl3):
d
¼3.69 (3H, s, OCH3),
(1H, br s, NH) ppm. 13C NMR (75 Hz, CDCl3):
d¼34.5, 43.8, 44.3, 52.8,
7.31e7.46 (8H, m, ArH), 8.11 (1H, d, J¼7.8 Hz, ArH), 8.39 (1H, br s, NH),
8.67 (1H, s, C4eH) ppm. 13C NMR (75 Hz, CDCl3):
d¼51.8,110.9,112.6,
66.5, 66.7, 102.9, 118.3, 118.6 (q, J¼4.5 Hz), 120.0 (q, J¼3.75 Hz), 124.3,
128.4, 128.6, 129.0, 129.1, 129.8 (q, J¼40 Hz), 130.6, 131.0, 137.5, 138.9,
150.2, 159.9, 167.9, 169.3, 188.1 ppm. Anal. Calcd for C27H25F3N4O4S:
C, 58.06; H, 4.51; N, 10.03. Found: C, 58.13; H, 4.66; N, 9.96.
120.3,120.6,121.9,122.0,123.0,123.4,126.5,126.9,127.8,128.6,140.2,
141.0,141.2,142.5,169.3 ppm. Anal. Calcd for C20H15NO2: C, 79.72; H,
5.02; N, 4.65. Found: C, 79.77; H, 4.95; N, 4.58. Data for compound 46
are in agreement with published previosly.23
4.4.11. 6-Methoxycarbonyl-2-morpholino-7-phenyl-4-(3-tri-
fluoromethylanilino)quinazoline 41. White crystals, yield 86% mp
179e180 ꢂC (from methanol). IR (KBr): nmax¼3369 (NH), 1711 (C]
4.4.17. 2-(4-Methylphenyl)-3-methoxycarbonyl-9H-carbazole
47. Yellowish crystals, yield 62% mp 183e185 ꢂC (from octane). IR
O) cmꢃ1
.
1H NMR (300 MHz, DMSO-d6):
d¼3.63 (3H, s, OCH3),
(KBr): nmax¼3395 (NH), 1730 (C]O) cmꢃ1
.
1H NMR (300 MHz,
¼2.43 (3H, s, CH3), 3.80 (3H, s, OCH3), 7.21e7.24 (2H, m,
3.67e3.70 (4H, m, N(CH2)2), 3.78e3.80 (4H, m, O(CH2)2), 7.35e7.49
(6H, m, ArH), 7.32 (1H, s, CH), 7.65 (1H, t, J¼8.1 Hz, ArH), 8.06 (1H, d,
J¼8.1 Hz, ArH), 8.38 (1H, br s, ArH), 8.89 (1H, s, CH), 10.29 (1H, br s,
CDCl3):
d
ArH), 7.28e7.34 (4H, m, ArH), 7.46e7.49 (2H, m, ArH), 8.14 (1H, dt,
J¼7.8, 0.9 Hz, ArH), 8.43 (1H, br s, NH), 8.68 (1H, d, J¼0.6 Hz, C4eH)
NH) ppm. 13C NMR (75 Hz, DMSO-d6):
(q, J¼3.75 Hz), 119.6 (q, J¼3 Hz), 123.7, 125.4, 126.1, 126.5, 127.5,
d
¼44.1, 51.7, 65.8,108.8,118.4
ppm. 13C NMR (75 Hz, CDCl3):
d
¼21.5, 52.1, 111.2, 112.9, 120.5, 120.9,
122.1, 122.2, 123.4, 123.6, 126.7, 128.7, 128.9, 136.8, 139.8, 140.5,