754
S. Kumar and D. P. Sahu
Vol 46
(m, 1H), 7.26–7.28 (m, 1H), 7.79–7.64 (m, 1H), 7.83–7.88 (m,
1H), 7.92 (dd, 4H, J ¼ 8.3, 0.9 Hz), 8.53 (d, 1H, J ¼ 8.5 Hz),
10.13 (s, NH); 13C NMR (75 MHz, CDCl3): d 112.59, 117.33,
119.68, 123.99, 126.21, 127.85, 127.97, 128.34, 134.47,
153.26, 156.75, 159.41; ES-MS (m/z): [MþH]þ 230; HRMS-
EI: found: 229.0357, calculated: 229.0407. Anal. Calcd. for
C12H8ClN3: C, 62.76; H, 3.51; N, 18.30. Found: C, 62.41; H,
3.67; N, 18.54.
4-(2-Chloroquinazolin-4-yl)naphthalene-1,7-diol (3fY).ield
60%; m.p.: >250ꢀC; IR (potassium bromide): 3452, 1585,
1
1352, 761 cmꢂ1; H NMR (200 MHz, DMSO-d6): d 6.77–6.86
(m, 2H), 7.10 (d, 1H, J ¼ 7.7 Hz), 7.27 (d, 1H, J ¼ 9.1 Hz),
7.35 (d, 1H, J ¼ 2.3 Hz), 7.45–7.58 (m, 2H), 7.88–7.89 (m,
2H), 9.6 (brs, 1H), 10.39 (brs, 1H); 13C NMR (50 MHz,
DMSO-d6): d 104.43, 107.64, 119.96, 123.45, 123.63, 126.57,
127.09, 127.72, 128.12, 128.73, 135.90, 152.52, 154.39,
155.24, 156.35, 172.96, 175.22; ES-MS (m/z): [MþH]þ 323;
HRMS-EI: found: 322.0507, calculated: 322.0509. Anal.
Calcd. for C18H11ClN2O2: C, 66.99; H, 3.44; N, 8.68. Found:
C, 66.79; H, 3.41; N, 8.61.
2-Chloro-4-(2-phenylindolizin-3-yl)quinazoline (3l). Yield
80%; m.p.: 192–194ꢀC; IR (potassium bromide): 2366, 1598,
;
1350, 767 cmꢂ1 1H NMR (300 MHz, CDCl3): d 6.72–6.77
(m, 1H), 6.78 (s, 1H), 6.98–7.08 (m, 2H), 7.10–7.15 (m, 5H),
7.53–7.59 (m, 2H), 7.63–7.68 (m, 1H), 7.87 (d, 1H, J ¼ 8.49
Hz), 8.99 (d, 1H, J ¼ 7.2 Hz); 13C NMR (75 MHz, CDCl3): d
101.55, 111.23, 114.25, 117.69, 119.95, 120.45, 123.43,
125.49, 125.70, 125.90, 127.24, 127.76, 133.15, 134.13,
134.22, 135.39, 151.99, 155.59, 161.36; ES-MS (m/z):
[MþH]þ 356; HRMS-EI: found: 355.0876, calculated:
355.0876. Anal. Calcd. for C22H14ClN3: C, 74.26; H, 3.97; N,
11.81. Found: C, 73.95; H, 4.13; N, 11.49.
2-Chloro-4-(1H-indol-3-yl)quinazoline (3g). Yield 77%;
m.p.: 175–177ꢀC; IR (potassium bromide): 1521, 1487, 1340
cmꢂ1
;
1H NMR (300 MHz, CDCl3þDMSO-d6): d 7.27–7.30
(m, 2H), 7.54–7.57 (m, 1H), 7.61–7.67 (m, 1H), 7.88–7.94 (m,
1H), 7.97–8.02 (m, 2H), 8.26–8.29 (m, 1H), 8.45 (dd, 1H, J ¼
8.1, 0.6 Hz), 11.57 (NH); 13C NMR (75 MHz,
CDCl3þDMSO-d6): d 111.91, 112.23, 121.12, 121.27, 121.40,
122.94, 126.03, 127.05, 127.25, 130.80, 133.98, 136.81,
152.17, 156.63, 166.35; FAB (m/z): 279, [MþH]þ 280;
HRMS-EI: found: 279.0494, calculated: 279.0485. Anal.
Calcd. for C16H10ClN3: C, 68.70; H, 3.60; N, 15.02. Found: C,
68.79; H, 3.68; N, 15.21.
2-Chloro-4-[2-(4-chlorophenyl)indolizin-3-yl]quinazoline (3m).
Yield 85%; m.p.: 218–220ꢀC; IR (potassium bromide): 1597,
1
1349, 773 cmꢂ1; H NMR (300 MHz, CDCl3): d 6.69–6.74 (m,
2H), 6.96–7.13 (m, 6H), 7.51 (d, 1H, J ¼ 8.9 Hz), 7.53 (dd, 1H,
J ¼ 8.6, 0.6 Hz), 7.66–7.71 (m, 1H), 7.87 (d, 1H J ¼ 8.5 Hz),
8.91 (dd, 1H, J ¼ 7.2, 0.6 Hz); 13C NMR (75 MHz, CDCl3): d
102.87, 112.90, 115.55, 119.18, 121.32, 122.07, 124.86, 127.29,
127.56, 128.41, 128.91, 130.32, 133.22, 134.04, 134.21, 134.89,
136.81, 153.53, 157.09, 162.54; ES-MS (m/z): [MþH]þ 390;
HRMS-EI: found: 389.0492, calcuated: 389.0487. Anal. Calcd.
for C22H13Cl2N3: C, 67.71; H, 3.36; N, 10.77. Found: C, 67.46;
H, 3.42; N, 10.63.
2-Chloro-4-(1-methyl-1H-indol-3-yl)quinazoline (3h). Yield
80%; m.p.: 142–144ꢀC; IR (potassium bromide): 1563, 1347,
1
735 cmꢂ1; H NMR (300 MHz, CDCl3): d 3.93 (s, 3H), 7.28–
7.36 (m, 2H), 7.38–7.43 (m, 1H), 7.55–7.61 (m, 1H), 7.78 (s,
1H), 7.84–7.89 (m, 1H), 7.97 (dd, 1H, J ¼ 8.3, 0.7 Hz), 8.17–
8.20 (m, 1H), 8.41 (dd, 1H, J ¼ 8.6, 0.7 Hz); 13C NMR (75
MHz, CDCl3): d 33.68 (CH3), 109.96 (CH), 112.19 (C),
121.53 (C), 122.04 (CH), 122.12 (CH), 123.52 (CH), 127.00
(C), 127.29 (CH), 127.46 (CH), 128.05 (CH), 133.93 (CH),
134.33 (CH), 137.65 (C), 152.90 (C), 157.37 (C), 166.15 (C);
ES-MS (m/z): [MþH]þ 294; HRMS-EI: found: 293.0689, calc-
uated: 293.0719. Anal. Calcd. for C17H12ClN3: C, 69.51; H,
4.12; N, 14.30. Found: C, 69.45; H, 4.10; N, 14.19.
4-[2-(4-Bromophenyl)indolizin-3-yl]-2-chloroquinazoline
(3n). Yield 85%; m.p.: 190–192ꢀC; IR (potassium bromide):
1597, 1348, 772cmꢂ1 1H NMR (300 MHz, CDCl3): d 6.70–
;
6.75 (m, 2H), 6.97–7.02 (m, 3H), 7.09–7.15 (m, 1H), 7.22–
7.25 (m, 2H), 7.50–7.55 (m, 2H), 7.67–7.73 (m, 1H), 7.88 (d,
1H, J ¼ 8.3 Hz), 8.91 (dd, 1H, J ¼ 7.1, 0.5 Hz); 13C NMR
(75 MHz, CDCl3): d 102.83, 112.94, 115.55, 119.22, 121.38,
121.45, 122.08, 124.90, 127.35, 127.64, 128.42, 130.66,
131.90, 134.05, 134.72, 134.94, 136.85, 157.15, 162.58; ES-
MS (m/z): [MþH]þ 434 (Br78), 436(Br80); HRMS-EI: found:
2-Chloro-4-(2-methyl-1H-indol-3-yl)quinazoline (3i). Yield
57%; m.p.: >250ꢀC; IR (potassium bromide): 1519, 1485,
1352 cmꢂ1
;
1H NMR (200 MHz, CDCl3þDMSO-d6): d 2.60
(s, 3H), 7.05–7.21 (m, 2H), 7.42–7.45 (m, 2H), 7.51–7.58 (m,
1H), 7.87–8.01 (m, 2H), 8.12 (d, 1H, J ¼ 8.3 Hz), 10.95 (brs,
1H); 13C NMR (50 MHz, CDCl3þDMSO-d6): d 13.67, 111.52,
119.62, 120.96, 122.18, 122.79, 127.26, 127.91, 128.18,
128.93, 134.88, 136.06, 139.67, 153.01, 157.41, 168.56; ES-
MS (m/z): [MþH]þ 294; HRMS-EI: found: 293.0718, calcu-
lated: 293.0719. Anal. Calcd. for C17H12ClN3: C, 69.51; H,
4.12; N, 14.30. Found: C, 69.35; H, 4.22; N, 14.22.
432.9950,
calcuated:
432.9981.
Anal.
Calcd.
for
C22H13BrClN3: C, 60.78; H, 3.01; N, 9.67. Found: C, 60.59;
H, 3.29; N, 9.43.
4-(2-Benzofuran-2-yl-indolizin-3-yl)-2-chloroquinazoline
(3o). Yield 80%; m.p.: 146–148ꢀC; IR (potassium bromide):
1596, 1350 1172, 765 cmꢂ1 1H NMR (300 MHz, CDCl3): d
;
2-Chloro-4-(2-phenyl-1H-indol-3-yl)quinazoline (3j). Yield
50%; m.p.: 260–262ꢀC; IR (potassium bromide): 3223, 1598,
6.49 (s, 1H), 6.67–6.71 (m, 1H), 6.94–6.99 (m, 1H), 7.02–7.12
(m, 4H), 7.17–7.22 (m, 1H), 7.36–7.39 (m, 1H), 7.52 (d, 1H,
J ¼ 8.9 Hz), 7.72–7.79 (m, 2H), 7.99 (d, 1H, J ¼ 8.3 Hz), 8.68
(d, 1H, J ¼ 7.2 Hz); 13C NMR (75 MHz, CDCl3): d 99.79,
103.04, 109.49, 111.60, 113.77, 117.96, 119.38, 120.36, 121.16,
121.49, 122.17, 122.87, 123.14, 126.27, 126.35, 127.39, 133.58,
135.01, 149.88, 151.95, 153.21, 155.61, 161.43; ES-MS (m/z):
[MþH]þ 396; HRMS-EI: found: 395.0831, calculated:
395.0825. Anal. Calcd. for C24H14ClN3O: C, 72.82; H, 3.56; N,
10.62. Found: C, 72.53; H, 3.70; N, 10.45.
1345, 747 cmꢂ1
;
1H NMR (300 MHz, CDCl3þDMSO-d6): d
7.09–7.15 (m, 1H), 7.23–7.28 (m, 4H), 7.32–7.39 (m, 3H),
7.55–7.82 (m, 2H), 7.73 (d, 1H, J ¼ 8.2 Hz), 7.84–7.93 (m,
2H); 13C NMR (75 MHz, CDCl3þDMSO-d6): d 106.57,
110.20, 117.70, 119.13, 120.14, 121.12, 125.47, 125.71,
126.32, 126.69, 126.96, 129.81, 133.24, 134.71, 138.15,
150.58, 154.79, 166.49; FAB (m/z): 355, [MþH]þ 356. Anal.
Calcd. for C22H14ClN3: C, 74.26; H, 3.97; N, 11.81. Found: C,
74.59; H, 3.89; N, 11.75.
General method for the preparation of 4-(hetero)aryl
quinolines 5a-c. 4-Chloro-2,8-bis(trifluoromethyl)quinoline 4
(1 mmol, 0.299 g) was added in 10 mL of dichloroethane.
Under stirring, to it was added AlCl3 (1.2 mmol, 0.158 g) and
2-Chloro-4-(1H-pyrrol-2-yl)quinazoline (3k). Yield 85ꢂ%1;
m.p.: 107–109ꢀC; IR (potassium bromide): 3220, 1550 cm
;
1H NMR (300 MHz, CDCl3): d 6.46–6.49 (m, 1H), 7.14–7.16
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet