Paper
CDCl
RSC Advances
3
) (d, ppm): 161.59, 161.09, 151.10, 146.59, 146.27, 141.99,
Ethyl 3-((1-(3-methoxyphenyl)-1H-1,2,3-triazol-4-yl)methyl)-4-
1
1
34.74, 130.19, 128.42, 128.17, 126.94, 126.09, 125.48, 121.89, oxo-3,4-dihydroquinazoline-2-carboxylate (5j). White solid, Rf
21.13, 121.15, 63.67, 55.93, 39.22, 13.93. IR nmax(neat): 3075 (] (5% methanol in DCM): 0.44, anal (C H N O ) calc. C 62.22 H
21
19 5 4
ꢀ1
1
CH), 1739 (C]O, ester) and 1678 (C]O, amide) cm . LC-MS: 4.72 N 17.27, found: C 62.17 H 4.66 N 17.25. H-NMR (300 MHz,
+
(m/z) [M + H] 406.2.
CDCl ) (d, ppm): 8.31 (d, J ¼ 8.1 Hz, 1H, Ar–H), 8.12 (s, 1H, ]CH),
3
Ethyl 3-((1-(2-nitrophenyl)-1H-1,2,3-triazol-4-yl)methyl)-4-oxo- 7.80–7.75 (m, 2H, Ar–H), 7.61–7.54 (m, 2H, Ar–H), 7.46–7.37 (m,
3
,4-dihydroquinazoline-2-carboxylate (5f). Yellow solid, R
f
(5% 2H, Ar–H), 7.19–7.12 (m, 1H, Ar–H), 5.66 (s, 2H, CH ), 4.60 (q, J ¼
2
methanol in DCM): 0.69, anal (C20
H
16
N
6
O
5
) calc. C 57.14 H 21.3 Hz, 2H, OCH ), 3.86 (s, 3H, CH ), 1.48 (t, J ¼ 14.4 Hz, 3H,
2
3
1
13
3.84 N 19.99, found: C 57.11 H 3.82 N 19.93. H-NMR (300 MHz, CH ). C-NMR (75 MHz, CDCl ) (d, ppm): 161.49, 161.16, 160.56,
3
3
CDCl ) (d, ppm): 8.29 (d, J ¼ 8.1 Hz, 1H, Ar–H), 8.08–8.05 (m, 1H, 146.42, 146.28, 143.29, 137.85, 134.86, 130.49, 128.53, 128.21,
3
Ar–H), 8.00 (s, 1H, ]CH), 7.81–7.66 (m, 4H, Ar–H), 7.61–7.54 (m, 127.66, 126.91, 121.80, 114.83, 112.45, 106.28, 63.74, 55.62, 39.52,
2
H, Ar–H), 5.68 (s, 2H, CH ), 4.59 (q, J ¼ 9.9 Hz, 2H, OCH ), 1.49 13.97. IR nmax(neat): 3090 (]CH), 1743 (C]O, ester) and 1663
2
2
13
ꢀ1
+
(
t, J ¼ 7.2 Hz, 3H, CH
3
). C-NMR (75 MHz, CDCl
3
) (d, ppm): (C]O, amide) cm . LC-MS: (m/z) [M + H] 406.1.
Ethyl 3-((1-(3-nitrophenyl)-1H-1,2,3-triazol-4-yl)methyl)-4-oxo-
1
1
1
1
61.48, 161.14, 146.36, 146.28, 144.39, 143.20, 134.88, 133.80,
30.88, 130.08, 128.55, 128.25, 128.12, 127.90, 126.91, 125.63, 3,4-dihydroquinazoline-2-carboxylate (5k). White solid, R (5%
f
25.13, 121.82, 63.83, 39.42, 13.93. IR nmax(neat): 3045 (]CH), methanol in DCM): 0.72, anal (C H N O ) calc. C 57.14 H
2
0
16 6 5
ꢀ1
1
739 (C]O, ester) and 1670 (C]O, amide) cm . LC-MS: (m/z) 3.84 N 19.99, found: C 57.10 H 3.82 N 19.95. H-NMR (300 MHz,
+
[M + H] 421.3.
CDCl ) (d, ppm): 8.58 (d, J ¼ 1.5 Hz, 1H, Ar–H), 8.34–8.27 (m, 2H,
3
Ethyl 3-((1-(3-chlorophenyl)-1H-1,2,3-triazol-4-yl)methyl)-4-oxo- Ar–H), 8.25 (s, 1H, ]CH), 8.15–8.11 (m, 1H, Ar–H), 7.82–7.56 (m,
3
,4-dihydroquinazoline-2-carboxylate (5g). White solid, R (5% 4H, Ar–H), 5.67 (s, 2H, CH ), 4.61 (q, J ¼ 21.3 Hz, 2H, OCH ), 1.49
f
2
2
1
3
m ethanol in DCM): 0.86, anal (C20
H
16ClN
5
O
3
) calc. C 58.61 H (t, J ¼ 14.1 Hz, 3H, CH ). C-NMR (75 MHz, CDCl ) (d, ppm):
3
3
1
3.94 Cl 8.65 N 17.09, found: C 58.58 H 3.90 Cl 8.61 N 17.06. H- 161.44, 161.19, 148.91, 146.24, 144.15, 137.56, 134.96, 130.95,
NMR (300 MHz, CDCl
3
) (d, ppm): 8.31 (d, J ¼ 7.8 Hz, 1H, Ar–H), 128.66, 128.25, 126.89, 125.89, 123.28, 121.77, 63.78, 39.67,
8.12 (s, 1H, ]CH), 7.83–7.74 (m, 3H, Ar–H), 7.61–7.54 (m, 1H, 13.98. IR nmax(neat): 3105 (]CH), 1736 (C]O, ester) and 1678
ꢀ1
+
Ar–H), 7.46–7.37 (m, 2H, Ar–H), 7.19–7.12 (m, 1H, Ar–H), 5.65 (s, (C]O, amide) cm . LC-MS: (m/z) [M + H] 421.2.
H, CH ), 4.59 (q, J ¼ 21.6 Hz, 2H, OCH ), 1.49 (t, J ¼ 7.2 Hz, 3H,
Ethyl 3-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methyl)-4-oxo-
CH ). C-NMR (75 MHz, CDCl ) (d, ppm): 161.47, 161.18, 3,4-dihydroquinazoline-2-carboxylate (5l). Light yellow solid, Rf
2
2
2
1
3
3
3
1
1
1
46.26, 143.65, 137.67, 135.58, 134.91, 130.81, 128.93, 128.58, (5% methanol in DCM): 0.76, anal (C H ClN O ) calc. C 58.61
20 16 5 3
28.23, 128.12, 127.66, 126.90, 125.66, 121.79, 63.78, 39.58, H 3.94 Cl 8.65 N 17.09, found: C 58.56 H 3.91 Cl 8.63 N 17.05.
1
3.97. IR nmax(neat): 3091 (]CH), 1739 (C]O, ester) and 1663
H-NMR (300 MHz, CDCl ) (d, ppm): 8.31 (d, J ¼ 7.8 Hz, 1H, Ar–
3
ꢀ1
+
(C]O, amide) cm . LC-MS: (m/z) [M + H] 410.1.
H), 8.11 (s, 1H, ]CH), 7.79 (d, J ¼ 3.6 Hz, 2H, Ar–H), 7.65 (d, J ¼
Ethyl 3-((1-(3-uorophenyl)-1H-1,2,3-triazol-4-yl)methyl)-4-oxo- 8.7 Hz, 2H, Ar–H), 7.60–7.54 (m, 1H, Ar–H), 7.48–7.45 (m, 2H,
3
,4-dihydroquinazoline-2-carboxylate (5h). White solid, R
f
(5% Ar–H), 5.65 (s, 2H, CH ), 4.60 (q, J ¼ 20.7 Hz, 2H, OCH ), 1.48 (t, J
2
3
2
1
methanol in DCM): 0.52, anal (C H FN O ) calc. C 61.07 H ¼ 14.1 Hz, 3H, CH ). C-NMR (75 MHz, CDCl ) (d, ppm): 161.47,
2
0
16
5
3
3
3
1
4.10 F 4.83 N 17.80, found: C 61.05 H 4.08 F 4.77 N 17.76. H- 161.18, 146.26, 135.34, 134.91, 134.67, 129.92, 128.58, 128.23,
NMR (300 MHz, CDCl ) (d, ppm): 8.31 (d, J ¼ 7.8 Hz, 1H, Ar– 126.89, 121.70, 63.77, 39.59, 13.97. IR nmax(neat): 3052 (]CH),
3
ꢀ1
H), 8.11 (s, 1H, ]CH), 7.79 (d, J ¼ 3.9 Hz, 1H, Ar–H), 7.59–7.42 1739 (C]O, ester) and 1657 (C]O, amide) cm . LC-MS: (m/z)
+
(
(
m, 4H, Ar–H), 7.19–7.10 (m, 2H, Ar–H), 5.66 (s, 2H, CH
q, J ¼ 21.3 Hz, 2H, OCH ), 1.48 (t, J ¼ 14.1 Hz, 3H, CH
) (d, ppm): 161.48, 161.39, 146.33, 3,4-dihydroquinazoline-2-carboxylate (5m). White crystalline
46.28, 143.62, 137.92, 134.89, 130.23, 131.11, 128.57, 128.24, solid, R (5% methanol in DCM): 0.69, anal (C H FN O ) calc.
2
), 4.59 [M + H] 410.1.
1
3
2
3
). C-
Ethyl 3-((1-(4-uorophenyl)-1H-1,2,3-triazol-4-yl)methyl)-4-oxo-
NMR (75 MHz, CDCl
3
1
1
1
f
20 16
5 3
28.11, 127.66, 126.90, 121.81, 121.70, 115.93, 63.76, 39.57, C 61.07 H 4.10 F 4.83 N 17.80, found: C 61.06 H 4.07 F 4.80 N
1
3.96.IR nmax(neat): 3069 (]CH), 1737 (C]O, ester) and 1657 17.75. H-NMR (300 MHz, CDCl ) (d, ppm): 8.31 (d, J ¼ 7.8 Hz,
3
ꢀ1
+
(
C]O, amide) cm . LC-MS: (m/z) [M + H] 394.2.
1H, Ar–H), 8.06 (s, 1H, ]CH), 7.79 (d, J ¼ 3.9 Hz, 2H, Ar–H),
Ethyl
dihydroquinazoline-2-carboxylate (5i). White solid,
methanol in DCM): 0.67, anal (C21
4-oxo-3-((1-m-tolyl-1H-1,2,3-triazol-4-yl)methyl)-3,4- 7.68–7.64 (m, 2H, Ar–H), 7.61–7.53 (m, 1H, Ar–H), 7.29–7.12 (m,
R
f
(5% 2H, Ar–H), 5.66 (s, 2H, CH ), 4.59 (q, J ¼ 21.6 Hz, 2H, OCH ), 1.48
2
2
1
3
H
19
N
5
O
3
) calc. C 64.77 H (t, J ¼ 14.1 Hz, 3H, CH ). C-NMR (75 MHz, CDCl ) (d, ppm):
3
3
1
4
.92 N 17.98, found: C 64.74 H 4.87 N 17.96. H-NMR (300 MHz, 161.48, 161.18, 146.38, 146.29, 143.50, 134.88, 133.17, 128.55,
CDCl
3
) (d, ppm): 8.32 (d, J ¼ 8.1 Hz, 1H, Ar–H), 8.07 (s, 1H, ] 128.23, 128.11, 127.66, 121.82, 63.75, 39.57, 13.96. IR nmax(neat):
ꢀ1
CH), 7.79 (d, J ¼ 3.6 Hz, 2H, Ar–H), 7.59–7.44 (m, 3H, Ar–H), 3067 (]CH), 1739 (C]O, ester) and 1657 (C]O, amide) cm
.
+
7
2
.38–7.11 (m, 2H, Ar–H), 5.66 (s, 2H, CH ), 4.59 (q, J ¼ 21.3 Hz, LC-MS: (m/z) [M + H] 394.3.
2
13
H, OCH ), 2.41 (s, 3H, CH ), 1.47 (t, J ¼ 14.1 Hz, 3H, CH ). C-
Ethyl
4-oxo-3-((1-p-tolyl-1H-1,2,3-triazol-4-yl)methyl)-3,4-
2
3
3
NMR (75 MHz, CDCl
3
) (d, ppm): 161.50, 161.16, 146.47, 146.30, dihydroquinazoline-2-carboxylate (5n). Off-white solid, R (5%
f
1
1
1
43.25, 139.96, 136.80, 134.83, 129.60, 128.20, 128.11, 127.66, methanol in DCM): 0.86, anal (C H N O ) calc. C 64.77 H
26.91, 125.65, 121.84, 121.72, 121.19, 63.73, 39.54, 22.64, 4.92 N 17.98, found: C 64.76 H 4.89 N 17.96. H-NMR (300 MHz,
2
1
19
5
3
1
3.96. IR nmax(neat): 3060 (]CH), 1737 (C]O, ester) and 1657 CDCl ) (d, ppm): 8.31 (d, J ¼ 7.8 Hz, 1H, Ar–H), 8.06 (s, 1H, ]
3
ꢀ1
+
(C]O, amide) cm . LC-MS: (m/z) [M + H] 390.2.
This journal is © The Royal Society of Chemistry 2018
RSC Adv., 2018, 8, 39611–39625 | 39619