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K. K. Roy et al. / Bioorg. Med. Chem. 20 (2012) 6313–6320
s, 1H), 7.49 (s, 1H), 7.26–7.24 (d, J = 7.71 Hz, 2H), 7.21–7.19 (d,
J = 5.94 Hz, 2H), 7.09–7.04 (t, J = 7.30 Hz, 1H), 6.88–6.87 (d,
J = 2.21 Hz, 1H), 6.81–6.77 (m, 1H), 6.71–6.68 (d, J = 8.88 Hz, 1H),
6.27–6.25 (d, J = 8.82 Hz, 1H), 4.47 (s, 2H), 3.42–3.38 (t, J = 5.55 Hz,
2H), 2.89–2.85 (t, J = 6.18 Hz, 2H), 2.33 (s, 3H), 2.11–2.03 (m, 2H).
13C NMR (CDCl3, 200 MHz). d ppm 155.12, 143.32, 140.19, 135.47,
134.68, 133.88, 132.51, 131.74, 130.26, 129.12, 127.52, 126.67,
125.58, 122.49, 120.45, 119.37, 114.44, 110.59, 59.83, 50.12, 27.34,
22.11, 20.84. FTIR (KBr): cmÀ1 3405, 2945, 2819, 2366, 1713, 1598,
1441, 1351, 1246, 1157, 972, 771, 692. ESMS: m/z 442 (M+1)+; HRMS
calcd for C24H22Cl2N2O2 (M+1)+ 441.1058; found 441.1153.
4.1.1.5.
1-(2,4-Dichlorobenzyl)-1,2,3,4-tetrahydroquinolin-6-yl
This compound was synthe-
3-chlorophenylcarbamate (6e).
sized using the general carbamoylation method by taking a solution
of 1-(2,4-dichlorobenzyl)-1,2,3,4-tetrahydroquinolin-6-ol (5, 1 mM)
and triethylamine (1.2 mM) in dry THF, and 3-chlorophenyl isocya-
nate (1.2 mM). % Yield: 80%; mp 125 °C, 1H NMR (CDCl3 + CD3OD,
300 MHz). d ppm 7.60 (s, 1H), 7.45–7.36 (m, 3H), 7.33–7.31 (m,
3H), 7.29–7.26 (m, 2H), 7.06–7.02 (m, 1H), 6.89–6.86 (m, 1H), 4.61
(s, 2H), 3.54–3.50 (t, J = 5.610 Hz, 2H), 2.98–2.93 (t, J = 6.375 Hz,
2H), 2.22–2.18 (m, 2H). 13C NMR (CDCl3, CD3OD, 200 MHz). d ppm
153.06, 142.61, 140.64, 139.40, 134.20, 133.94, 133.18, 132.71,
129.56, 129.01, 128.30, 126.86, 122.86, 121.78, 119.64, 118.41,
116.44, 110.66, 59.95, 53.11, 49.82, 27.77, 21.97. FTIR (KBr): cmÀ1
3677, 3287, 2931, 2365, 2334, 1714, 1615, 1593, 1478, 1299,
1231, 1195, 1055, 757. ESMS: m/z: 461 (M+); HRMS calcd for
4.1.1.2. 1-(2,4-Dichlorobenzyl)-1,2,3,4-tetrahydroquinolin-6-yl
m-tolylcarbamate (6b).
This compound was synthesized
using the general carbamoylation method by taking a solution of
1-(2,4-dichlorobenzyl)-1,2,3,4-tetrahydroquinolin-6-ol (5, 1 mM)
and triethylamine (1.2 mM) in dry THF, and m-tolyl isocyanate
(1.2 mM). % Yield: 81%; 1H NMR (CDCl3, 300 MHz). d ppm 8.17
(br s, 1H), 7.40–7.34 (m, 3H), 7.28–7.23 (m, 1H), 7.16 (s, 1H),
7.02–6.97 (m, 1H), 6.85–6.84 (d, J = 2.35 Hz, 1H), 6.78–6.74 (d,
J = 9.98 Hz, 2H), 6.24–6.21 (d, J = 8.78 Hz, 1H), 4.44 (s, 2H), 3.38–
3.34 (t, J = 5.535 Hz, 2H), 2.86–2.83 (t, J = 6.105 Hz, 2H), 2.30 (s,
3H), 2.09–2.02 (m, 2H). 13C NMR (CDCl3, 200 MHz). d ppm
154.82, 143.44, 141.20, 138.72, 136.00, 135.45, 134.81, 133.91,
131.23, 130.12, 128.25, 126.76, 125.30, 124.48, 123.15, 121.56,
120.44, 119.53, 118.49, 110.51, 60.12, 49.99, 27.52, 22.83, 21.24,
20.76. FTIR (Neat): cmÀ1 3410, 2948, 2823, 2387, 1714, 1598,
1348, 1254, 1157, 975, 771. ESMS: m/z: 442 (M+1)+; HRMS calcd
for C24H22Cl2N2O2 (M+1)+ 441.1058; found 441.1156.
C
23H19Cl3N2O2 (M+) 461.0512; found 461.0573.
4.1.1.6. 1-(2,4-Dichlorobenzyl)-1,2,3,4-tetrahydroquinolin-6-yl 4-
chlorophenylcarbamate (6f). This compound was synthesized
using the general carbamoylation method by taking a solution of 1-
(2,4-dichlorobenzyl)-1,2,3,4-tetrahydroquinolin-6-ol (5, 1 mM) and
triethylamine (1.2 mM) in dry THF, and 4-chlorophenyl isocyanate
(1.2 mM).
%
Yield: 82%; mp 158 °C, 1H NMR NMR (CD3OD,
300 MHz). d ppm 7.89 (br s, 1H), 7.47–7.46 (d, J = 4.62 Hz, 1H),
7.43–7.40 (m, 2H), 7.37 (s, 1H), 7.27–7.24 (m, 2H), 7.18–7.17 (d,
J = 1.5 Hz, 2H), 6.83–6.82 (d, J = 2.76 Hz, 1H), 6.25–6.22 (d,
J = 8.82 Hz, 1H), 4.47 (s, 2H), 3.42–3.38 (t, J = 5.640 Hz, 2H), 2.87–
2.83 (t, J = 6.225 Hz, 2H), 2.09–2.02 (m, 2H). 13C NMR (CDCl3, CD3OD,
200 MHz). d ppm 153.21, 142.43, 140.58, 136.76, 134.52, 133.86,
133.04, 132.57, 128.83, 128.27, 127.64, 126.68, 122.72, 121.64,
119.89, 119.50, 110.50, 59.65, 52.91, 49.67, 48.92, 27.60, 21.82. FTIR
(KBr): cmÀ1 3332, 3106, 3033, 2929, 2844, 2367, 1713, 1601, 1542,
1507, 1349, 1220, 1195, 1012, 826, 691, 560. ESMS: m/z 461 (M+);
HRMS calcd for C23H19Cl3N2O2 (M+) 461.0512; found 461.0533.
4.1.1.3. 1-(2,4-Dichlorobenzyl)-1,2,3,4-tetrahydroquinolin-6-yl
p-tolylcarbamate (6c).
This compound was synthesized
using the general carbamoylation method by taking a solution of
1-(2,4-dichlorobenzyl)-1,2,3,4-tetrahydroquinolin-6-ol (5, 1 mM)
and triethylamine (1.2 mM) in dry THF, and p-tolyl isocyanate
(1.2 mM). % Yield: 78%; mp 130 °C, 1H NMR (CDCl3, 300 MHz). d
ppm 7.40–7.38 (d, J = 6.33 Hz, 1H), 7.31–7.28 (d, J = 8.18 Hz, 1H),
7.26–7.25 (d, J = 4.95 Hz, 2H), 7.22–7.15 (m, 2H), 7.12–7.09 (m,
2H), 6.83–6.82 (d, J = 2.64 Hz, 1H), 6.76–6.69 (m, 1H), 6.23–6.16
(m, 1H), 4.44 (s, 2H), 3.38–3.34 (t, J = 5.565 Hz, 2H), 2.85–2.81 (t,
J = 6.375 Hz, 2H), 2.30 (s, 3H), 2.05–1.99 (m, 2H). 13C NMR (CDCl3,
200 MHz). d ppm 155.96, 143.37, 142.93, 135.07, 134.25, 133.93,
133.52, 133.05, 129.58, 128.62, 128.41, 127.23, 123.09, 122.19,
121.53, 120.72, 120.05, 119.81, 118.81, 111.05, 50.17, 28.14,
22.33, 21.20. FTIR (KBr): cmÀ1 3403, 2965, 2839, 2366, 1713,
1600, 1496, 1348, 1239, 1157, 998, 762, 686. ESMS: m/z 442
(M+1)+; HRMS calcd for C24H22Cl2N2O2 (M+1)+ 441.1058; found
441.1154.
4.1.1.7. 1-(2,4-Dichlorobenzyl)-1,2,3,4-tetrahydroquinolin-6-yl 3-
bromophenylcarbamate(6g).
Thiscompoundwassynthesized
using the general carbamoylation method by taking a solution of 1-
(2,4-dichlorobenzyl)-1,2,3,4-tetrahydroquinolin-6-ol (5, 1 mM) and
triethylamine (1.2 mM) in dry THF, and 3-bromophenyl isocyanate
(1.2 mM). % Yield: 80%; mp: 132 °C; 1H NMR (CDCl3, 300 MHz). d
ppm 7.59 (s, 1H), 7.44–7.35 (m, 3H), 7.33–7.31 (m, 3H), 7.27–7.24
(d, J = 2.58 Hz, 1H), 7.01–6.98 (m, 1H), 6.85–6.81 (m, 1H), 4.52 (s,
2H), 3.53–3.50 (t, J = 5.613 Hz, 2H), 2.97–2.93 (t, J = 6.372 Hz, 2H),
2.25–2.14 (m, 2H). 13C NMR (CDCl3, 200 MHz). d ppm 153.16,
142.71, 140.73, 139.49, 134.29, 134.04, 133.28, 132.81, 129.65,
129.11, 128.39, 126.96, 122.96, 121.88, 119.74, 118.51, 116.54,
110.75, 58.98, 53.65, 49.92, 27.87, 22.07. FTIR (KBr) cmÀ1 3316,
3039, 2936, 2844, 2368, 1712, 1605, 1505, 1359, 1021, 828, 771,
666. ESMS: m/z 505 (M+1)+; HRMS calcd for C23H19BrCl2N2O2
(M+1)+ 505.0007; found 505.0023.
4.1.1.4. 1-(2,4-Dichlorobenzyl)-1,2,3,4-tetrahydroquinolin-6-yl 2-
chlorophenylcarbamate (6d).
Thiscompoundwas synthesized
using the general carbamoylation method bytaking a solution of 1-(2,
4-dichlorobenzyl)-1,2,3,4-tetrahydroquinolin-6-ol (5, 1 mM) and tri-
ethylamine (1.2 mM) in dry THF, and 2-chlorophenyl isocyanate
(1.2 mM). % Yield: 81%; mp 222 °C, 1H NMR (CDCl3, 300 MHz). d
ppm 8.17 (br s, 1H), 7.40–7.34 (m, 3H), 7.28–7.23 (m, 2H), 7.16 (s,
1H), 7.02–6.97 (m, 1H), 6.85–6.84 (d, J = 2.28 Hz, 1H), 6.78–6.74 (d,
J = 2.61 Hz, 1H), 6.24–6.21 (d, J = 8.82 Hz, 1H), 4.44 (s, 2H), 3.38–
3.34 (t, J = 5.535 Hz, 2H), 2.86–2.83 (t, J = 6.105 Hz, 2H), 2.09–2.02
(m, 2H). 13C NMR (CDCl3, CD3OD 200 MHz). d ppm 153.14, 140.58,
134.20, 134.00, 133.32, 132.88, 129.19, 128.98, 128.40, 127.57,
127.20, 127.03, 124.07, 123.77, 122.42, 121.84, 119.74, 110.84,
60.19, 53.28, 49.96, 27.93, 22.09. FTIR (KBr): cmÀ1 3677, 3291, 2928,
2364, 2340, 1713, 1591, 1476, 1386, 1294, 1232, 1197, 1054, 752.
ESMS: m/z 461 (M+); HRMS calcd for C23H19Cl3N2O2 (M+) 461.0512;
found 461.0578.
4.1.1.8. 1-(2,4-Dichlorobenzyl)-1,2,3,4-tetrahydroquinolin-6-yl 2-
methoxyphenylcarbamate (6h).
This compound was synthe-
sized using the general carbamoylation method by taking a solution
of 1-(2,4-dichlorobenzyl)-1,2,3,4-tetrahydroquinolin-6-ol (5, 1 mM)
and triethylamine (1.2 mM) in dry THF, and 2-methoxyphenyl isocy-
anate (1.2 mM). % Yield:81%; mp158 °C; 1H NMR (CDCl3, 300 MHz). d
ppm 8.15 (br s, 1H), 7.42–7.34 (m, 3H), 7.27–7.21 (m, 1H), 7.17 (s, 1H),
7.00–6.95 (m, 2H), 6.87–6.75 (m, 2H), 6.22–6.19 (d, J = 8.84 Hz, 1H),
4.44 (s, 2H), 4.32 (s, 3H), 3.38–3.33 (t, J = 5.537 Hz, 2H), 2.86–2.82 (t,
J = 6.111 Hz, 2H), 2.07–2.01 (m, 2H). 13C NMR (CDCl3, 200 MHz). d
ppm 153.21, 141.08, 134.32, 134.11, 133.33, 133.00, 129.22, 128.52,
127.64, 127.27, 124.13, 124.03, 122.93, 122.34, 121.88, 120.31,
119.44, 110.64, 60.04, 58.65, 53.35, 49.98, 27.87, 22.04. FTIR (KBr):
cmÀ1 3676, 3290, 2928, 2364, 2340, 1712, 1647, 1591, 1476, 1386,