11 of 14
ASGARI ET AL.
|
DMSO‐d6) δ 3.59 (s, 3H, OCH3), 5.01 (s, 2H, N–CH2), 5.81 (s, 2H,
O–CH2), 5.92 (s, 1H, alkene), 6.53 (d, J = 8.3 Hz, 1H, Ar), 6.59 (s, 1H,
Ar), 6.89 (d, J = 8.4 Hz, 1H, Ar), 7.06 (s, 1H, Ar), 7.39 (d, J = 8.7 Hz, 1H,
Ar), 7.48 (t, J = 8.0 Hz, 2H, Ar), 8.18 (s, 1H, triazole), 9.86 (s, 2H, NH).
13C NMR (126 MHz, DMSO) δ 44.07, 48.02, 54.95, 112.16, 113.17,
118.30, 120.30, 120.32, 124.28, 124.86, 125.22, 128.42, 129.83,
131.07, 131.15, 135.39, 136.38, 142.26, 144.55, 148.00, 172.27,
173.62 ppm. Anal. calcd. for C22H18FN5O5: C, 58.54; H, 4.02; N,
15.51. Found: C, 58.39; H, 4.15; N, 15.68.
DMSO‐d6) δ 3.60 (s, 3H, OCH3), 5.04 (s, 2H, N–CH2), 5.62 (s, 2H,
O–CH2), 5.92 (s, 1H, alkene), 6.56 (s, 1H, Ar), 6.64 (s, 1H, Ar), 6.87 (s,
1H, Ar), 7.30 (s, 1H, Ar), 7.32 (d, J = 7.7 Hz, 1H, Ar), 7.55 (s, 2H, Ar),
8.28 (s, 1H, triazole), 10.13 (s, 2H, NH). 13C NMR (126 MHz, DMSO) δ
51.4, 54.9, 61.5, 111.1, 113.2, 121.3, 124.3, 126.5, 130.2, 130.4,
137.7, 138.1, 142.9, 144.3, 147.9, 150.2, 163.0, 165.9 ppm. Anal.
calcd. for C22H18BrN5O5: C, 51.58; H, 3.54; N, 13.67. Found: C,
51.41; H, 3.67; N, 13.84.
5‐(4‐{[1‐(4‐Bromobenzyl)‐1H‐1,2,3‐triazol‐5‐yl]methoxy}‐3‐
methoxybenzylidene)pyrimidine‐2,4,6(1H,3H,5H)‐trione (8h)
White solid; yield: 78%, mp: 211–213°C. IR (KBr): 1,688 (C═O), 1,639
5‐(4‐{[1‐(2‐Chlorobenzyl)‐1H‐1,2,3‐triazol‐5‐yl]methoxy}‐3‐
methoxybenzylidene)pyrimidine‐2,4,6(1H,3H,5H)‐trione (8d)
White solid; yield: 76%, mp: 196–200°C. IR (KBr): 1,680 (C═O), 1,645
(C═C alkene), 2,922 (C–H aromatic) cm−1 1H NMR (500 MHz,
.
(C═C alkene), 2,926 (C–H aromatic) cm−1
.
1H NMR (500 MHz,
DMSO‐d6) δ 3.59 (s, 3H, OCH3), 5.02 (s, 2H, N–CH2), 5.59 (s, 2H,
O–CH2), 5.92 (s, 1H, alkene), 6.56 (s, 1H, Ar), 6.64 (s, 1H, Ar), 6.89 (d,
J = 8.2 Hz, 1H, Ar), 7.28 (d, J = 8.1 Hz, 2H, Ar), 7.57 (d, J = 8.1 Hz, 2H,
Ar), 8.25 (s, 1H, triazole), 10.10 (s, 2H, NH). 13C NMR (126 MHz,
DMSO) δ 51.4, 55.4, 61.7, 111.8, 113.4, 118.8, 121.4, 124.0, 129.7,
131.1, 134.9, 137.7, 142.9, 144.3, 147.9, 150.2, 163.3, 165.5 ppm.
Anal. calcd. for C22H18BrN5O5: C, 51.58; H, 3.54; N, 13.67. Found: C,
51.33; H, 3.39; N, 13.51.
DMSO‐d6) δ 3.60 (s, 3H, OCH3), 5.05 (s, 2H, N–CH2), 5.72 (s, 2H,
O–CH2), 5.92 (s, 1H, alkene), 6.57 (d, J = 8.3 Hz, 1H, Ar), 6.64 (s, 1H,
Ar), 6.89 (d, J = 8.4 Hz, 1H, Ar), 7.19 (d, J = 8.6 Hz, 1H, Ar), 7.38 (dt,
J = 19.7, 7.1 Hz, 2H, Ar), 7.52 (d, J = 7.7 Hz, 1H, Ar), 8.22 (s, 1H,
triazole), 10.06 (s, 2H, NH). 13C NMR (126 MHz, DMSO) δ 43.3, 50.0,
54.9, 61.4, 90.5, 111.0, 111.1, 113.1, 113.2, 118.3, 124.5, 127.2,
129.0, 132.0, 133.0, 137.8, 142.9, 144.5, 147.9, 150.2, 163.2, 163.7,
165.3 ppm. Anal. calcd. for C22H18ClN5O5: C, 56.48; H, 3.88; N,
14.97. Found: C, 56.57; H, 3.74; N, 14.86.
5‐(3‐Methoxy‐4‐{[1‐(4‐nitrobenzyl)‐1H‐1,2,3‐triazol‐5‐yl)methoxy}‐
benzylidene}pyrimidine‐2,4,6(1H,3H,5H)‐trione (8i)
5‐(4‐{[1‐(4‐Chlorobenzyl)‐1H‐1,2,3‐triazol‐5‐yl]methoxy}‐3‐
methoxybenzylidene)pyrimidine‐2,4,6(1H,3H,5H)‐trione (8e)
White solid; yield: 70%, mp: 189–194°C. IR (KBr): 1,705 (C═O), 1,597
White solid; yield: 70%, mp: 201–207°C. IR (KBr): 1,336–1,352
(NO2), 1,678 (C═O), 1,605 (C═C alkene), 3,035 (C–H aromatic) cm−1. 1H
NMR (500 MHz, DMSO‐d6) δ 3.60 (s, 3H, OCH3), 5.13 (s, 2H, N–CH2),
5.99–5.72 (m, 3H), 7.09 (s, 1H, Ar), 7.45–7.29 (m, 1H, Ar), 7.56 (d,
J = 8.2 Hz, 2H, Ar), 8.48–8.17 (m, 4H), 10.02–9.52 (m, 2H, NH). 13C NMR
(126 MHz, DMSO) δ 47.6, 51.1, 55.0, 61.6, 112.5, 113.0, 118.7, 123.4,
124.0, 125.4, 128.5, 130.8, 137.8, 138.5, 139.2, 143.4, 149.8, 150.3,
163.9, 165.3, 167.4 ppm. Anal. calcd. for C22H18N6O7: C, 55.23; H, 3.79;
N, 17.57. Found; C, 55.37; H, 3.84; N, 17.65.
(C═C alkene), 2,966 (C–H aromatic) cm−1 1H NMR (500 MHz,
.
DMSO‐d6) δ 3.60 (s, 3H, OCH3), 5.04 (s, 2H, N–CH2), 5.70 (s, 2H,
O–CH2), 5.91 (s, 1H, alkene), 6.88 (s, 1H, Ar), 7.29 (s, 2H, Ar), 7.47 (s,
2H, Ar), 7.69 (s, 1H, Ar), 8.24 (s, 1H, triazole), 9.86 (s, 1H, NH), 10.06
(s, 1H, NH). 13C NMR (126 MHz, DMSO) δ 49.5, 54.9, 60.9, 109.2,
111.1, 112.2, 113.2, 118.3, 124.5, 125.8, 127.3, 128.5, 130.9, 133.0,
137.6, 142.5, 144.9, 147.4, 150.3, 162.1, 165.3 ppm. Anal. calcd. for
C22H18ClN5O5: C, 56.48; H, 3.88; N, 14.97. Found: C, 56.31; H, 3.71;
N, 15.08.
5‐(3‐Methoxy‐4‐{[1‐(2‐methylbenzyl)‐1H‐1,2,3‐triazol‐5‐yl]methoxy}‐
benzylidene)‐2‐thioxodihydropyrimidine‐4,6(1H,5H)‐dione (8j)
White solid; yield: 86%, mp: 96–98°C. IR (KBr): 1,715
5‐(4‐{[1‐(2,4‐Dichlorobenzyl)‐1H‐1,2,3‐triazol‐5‐yl]methoxy}‐3‐
methoxybenzylidene)pyrimidine‐2,4,6(1H,3H,5H)‐trione (8f)
White solid; yield: 74%, mp: 200–203°C. IR (KBr): 1,700 (C═O), 1,626
(C═C alkene), 2,926 (C–H aromatic) cm−1. 1H NMR (500 MHz, DMSO‐d6)
δ 3.81 (s, 3H, OCH3), 5.27 (s, 2H, N–CH2), 5.73 (s, 2H, O–CH2), 5.99 (s,
1H, alkene), 7.32 (s, 1H, Ar), 7.40 (s, 2H, Ar), 7.48 (s, 1H, Ar), 7.56 (s, 1H,
Ar), 7.72 (s, 1H, Ar), 8.32 (s, 1H, triazole), 9.65–10.00 (m, 2H, NH). 13C
NMR (126 MHz, DMSO) δ 49.6, 54.9, 61.1, 109.7, 112.2, 125.0, 125.2,
127.4, 128.6, 129.4, 131.5, 133.5, 141.6, 146.2, 152.2, 166.8, 168.7 ppm.
Anal. calcd. for C22H17Cl2N5O5: C, 52.61; H, 3.41; N, 13.94. Found: C,
52.75; H, 3.62; N, 14.05.
(C═O), 1,646 (C═C alkene), 2,928 (C–H aromatic) cm−1 1H NMR
.
(500 MHz, DMSO‐d6) δ 2.30 (CH3, s, 3H), 3.59 (s, 3H, OCH3),
5.03 (s, 2H, N–CH2), 5.61 (s, 2H, O–CH2), 5.93 (s, 1H, alkene), 6.89 (d,
J = 8.4 Hz, 1H, Ar), 7.06 (s, 2H, Ar), 7.18 (s, 1H, Ar), 7.23 (s, 2H, Ar), 7.32 (s,
1H, Ar), 8.12 (s, 1H, triazole), 10.04 (s, 2H, NH) ppm. 13C NMR (126 MHz,
DMSO) δ 18.07, 43.92, 50.36, 54.95, 113.04, 118.28, 120.33, 122.44,
124.12, 125.70, 127.74, 128.07, 128.17, 129.85, 129.91, 129.95, 133.60,
133.71, 135.71, 142.62, 154.63, 161.75 ppm. Anal. calcd. for
C23H21N5O4S: C, 59.60; H, 4.57; N, 15.11. Found: C, 59.74; H, 4.68;
N, 15.01.
5‐(4‐{[1‐(2‐Fluorobenzyl)‐1H‐1,2,3‐triazol‐5‐yl]methoxy}‐3‐
methoxybenzylidene)‐2‐thioxodihydropyrimidine‐4,6(1H,5H)‐
dione (8k)
5‐(4‐{[1‐(3‐Bromobenzyl)‐1H‐1,2,3‐triazol‐5‐yl]methoxy}‐3‐
methoxybenzylidene)pyrimidine‐2,4,6(1H,3H,5H)‐trione (8g)
White solid; yield: 75%, mp: 212–214°C. IR (KBr): 1,692 (C═O), 1,646
White solid; yield: 87%; mp: 108–110°C. IR (KBr): 1,713 (C═O),
(C═C alkene), 1,156, 2,925 (C–H aromatic) cm−1
.
1H NMR (500 MHz,
1,653 (C═C alkene), 2,919 (C–H aromatic) cm−1 1H NMR (500 MHz,
.