LUCESCU ET AL.
7 of 11
|
7.41–7.47 (m, 1 H, ArH), 7.52 (s, 1 H, ArH), 7.76 (d, J = 8.0, 1.6 Hz, 1 H,
ArH), 8.16 (d, J = 7.2 Hz, 1 H, ArH), 7.89 (s, 1 H, ArH). 13C NMR
(100 MHz, CDCl3): δ = 55.8 (2 CH3), 106.3 (CH), 125.0 (CH), 127.0
(CH), 130.1 (C), 130.4 (CH), 130.5 (CH), 135.2 (C), 162.1 (C), 165.1
(C), 166.6 (C), 173.0 (2 C). Anal. calcd. for C14H11ClN4O3: C, 52.76; H,
3.48; N, 17.58. Found: C, 53.01; H, 3.62; N, 17.77%.
(100 MHz, CDCl3): 19.8 (2 CH3), 55.7 (2 CH3), 106.5 (CH), 124.3 (CH),
125.8 (C), 127.9 (CH), 130.3 (CH), 137.4 (C), 139.3 (C), 163.2 (C),
165.3 (C), 165.9 (C), 173.0 (2 C). Anal. calcd. for C16H16N4O3: C,
61.53; H, 5.16; N, 17.94. Found: C, 61.82; H, 5.50; N, 18.11%.
2‐[3‐(3‐Fluoro‐4‐methoxyphenyl)isoxazol‐5‐yl]‐4,6‐
dimethoxy‐1,3,5‐triazine (3g)
The general procedure was followed using 2‐ethynyl‐4,6‐dimethoxy‐
1,3,5‐triazine 1 (0.7 g, 4.24 mmol, 1 equiv), 3‐fluoro‐4‐methoxybenz‐
aldoxime 5g (0.8 g, 4.72 mmol, 1.1 equiv), N‐chlorosuccinimide
(0.68 g, 5.1 mmol, 1.2 equiv), KHCO3 (2.12 g, 20.12 mmol, 5 equiv),
and ethyl acetate (50 ml). Yield: 0.75 g (56%); white solid, mp (EtOH)
160–163°C; Rf = 0.6 (EtOAc/n‐hexane, 1:1). IR (neat): 1619, 1549,
1509, 1460, 1389, 1355, 1317, 1280, 1130, 1104, 1017, 934, 870,
762 cm−1. 1H NMR (400 MHz, CDCl3): δ = 3.96 (s, 3 H, OCH3), 4.16 (s,
6 H, 2 OCH3), 7.06 (t, J = 8.6 Hz, 1 H, ArH), 7.47 (s, 1 H, ArH), 7.60 (dt,
J = 8.6, 1.2 Hz, 1 H, ArH), 7.64 (dd, J = 11.8 Hz, 1 H, ArH).
13C NMR (100 MHz, CDCl3): 55.8 (2 CH3), 56.3 (CH3), 106.2 (CH),
113.5 (d, J = 2.3 Hz, CH), 114.7 (d, J = 20.2 Hz, CH), 121.2
(d, J = 7.2 Hz, C), 123.2 (d, J = 3.1 Hz, CH), 149.5 (d, J = 10.3 Hz, C),
152.5 (d, J = 246.7 Hz, CF), 162.0 (d, J = 2.6 Hz, C), 165.1 (C), 166.3
(C), 173.0 (2 C). Anal. calcd. for C15H13FN4O4: C, 54.22; H, 3.94;
N, 16.86. Found: C, 54.46; H, 4.14; N, 17.07%.
N‐{4‐[5‐(4,6‐Dimethoxy‐1,3,5‐triazine‐2‐yl)isoxazol‐3‐yl]‐
phenyl}‐N,N‐dimethylamine (3d)
The general procedure was followed using 2‐ethynyl‐4,6‐dimethoxy‐
1,3,5‐triazine 1 (0.9 g, 5.46 mmol, 1 equiv), 4‐dimethylaminobenzaldox-
ime 5d (1.0 g, 6.06 mmol, 1.1 equiv), N‐chlorosuccinimide (0.86 g,
6.44 mmol, 1.2 equiv), KHCO3 (2.72 g, 27.2 mmol, 5 equiv), and ethyl
acetate (40 ml). Yield: 0.12 g (10%); yellow solid, mp (EtOH) 180–184°C;
Rf = 0.75 (EtOAc/n‐hexane, 1:1). IR (neat): 1611, 1539, 1504, 1457,
1434, 1387, 1357, 1228, 1196, 1174, 1036, 981, 815, 796, 757 cm−1
.
1H NMR (400 MHz, CDCl3): δ = 3.05 (s, 6 H, 2CH3), 4.15
(s, 6 H, 2 OCH3), 6.88 (s, 2 H, ArH), 7.47 (s, 1 H, ArH), 7.77 (d,
J = 8.4 Hz, 2 H, ArH). 13C NMR (100 MHz, CDCl3): 40.3 (2 CH3), 55.7
(2 CH3), 98.4 (CH), 114.8 (2 CH), 122.6 (C), 128.2 (2 CH), 149.6 (C),
165.3 (C), 165.9 (C), 173.0 (2 C), 173.1 (C). Anal. calcd. for C16H17N5O3:
C, 58.71; H, 5.23; N, 21.39. Found: C, 59.04; H, 5.50; N, 21.62%.
2‐[3‐(2,5‐Dimethoxyphenyl)isoxazol‐5‐yl]‐4,6‐dimethoxy‐
1,3,5‐triazine (3e)
2‐[3‐(2,6‐Dichlorophenyl)isoxazol‐5‐yl]‐4,6‐dimethoxy‐1,3,5‐
triazine (3h)
The general procedure was followed using 2‐ethynyl‐4,6‐dimethoxy‐
1,3,5‐triazine 1 (0.30 g, 1.82 mmol, 1 equiv), 2,5‐dimethoxybenzaldox-
ime 5e (0.36 g, 4.02 mmol, 1.1 equiv), N‐chlorosuccinimide (0.29 g,
2.18 mmol, 1.2 equiv), KHCO3 (0.9 g, 9.08 mmol, 5 equiv), and ethyl
acetate (30 ml). Yield: 0.26 g (42%); beige solid, mp (EtOH) 177–179°C;
Rf = 0.45 (EtOAc/n‐hexane, 1:1). IR (neat): 1541, 1512, 1460, 1421,
1376, 1301, 1263, 1116, 1029, 983, 807, 739 cm−1. 1H NMR (400 MHz,
CDCl3): δ = 3.84 (s, 3 H, OCH3), 3.88 (s, 3 H, OCH3), 4.16
(s, 6 H, 2 OCH3), 6.97 (s, 1 H, ArH), 6.99 (d, J = 3.2 Hz, 1 H, ArH), 7.55
(d, J = 2.8 Hz, 1 H, ArH), 7.99 (s, 1 H, ArH). 13C NMR (100 MHz, CDCl3):
55.7 (2 CH3), 55.9 (CH3), 56.1 (CH3), 110.2 (CH), 112.9 (CH), 113.5 (CH),
117.5 (C), 117.8 (CH), 151.7 (C), 153.6 (C), 160.7 (C), 165.1 (C), 165.5
(C), 173.0 (2 C). Anal. calcd. for C16H16N4O5: C, 55.81; H, 4.68; N, 16.27.
Found: C, 56.11; H, 4.90; N, 16.54%.
The general procedure was followed using 2‐ethynyl‐4,6‐dimethoxy‐
1,3,5‐triazine 1 (0.3 g, 1.82 mmol, 1 equiv), 2,6‐dichlorobenzaldoxime 5h
(0.38 g, 2.0 mmol, 1.1 equiv), N‐chlorosuccinimide (0.3 g, 2.18 mmol, 1.2
equiv), KHCO3 (0.9 g, 8.9 mmol, 5 equiv), and ethyl acetate (30 ml).
Yield: 0.46 g (71%); beige solid, mp (EtOH) 150–152°C; Rf = 0.66
(EtOAc/n‐hexane, 1:1). IR (neat): 1546, 1514, 1493, 1453, 1386, 1233,
1105, 1046, 940, 851, 731 cm−1. 1H NMR (500 MHz, CDCl3): δ = 4.16 (s,
6 H, 2 OCH3), 7.33 (s, 1 H, ArH), 7.35–7.39 (m, 1 H, ArH), 7.45 (d,
J = 8.0 Hz, 2 H, ArH). 13C NMR (125 MHz, CDCl3): 55.9 (2 CH3), 110.3
(CH), 127.7 (C), 128.4 (2 CH), 131.6 (CH), 135.7 (2 C), 159.7 (C), 165.2
(C), 166.1 (C), 173.1 (2 C). MS (EI) m/z (%): 352 (44) [M+], 317 (36), 214
(62), 212 (100), 184 (25), 157 (10). Anal. calcd. for C14H10Cl2N4O3: C,
47.61; H, 2.85; N, 15.86. Found: C, 47.80; H, 3.20; N, 16.00%.
2,4‐Dimethoxy‐6‐[3‐(3,4,5‐trimethoxyphenyl)‐
2‐[3‐(3,4‐Dimethylphenyl)isoxazol‐5‐yl]‐4,6‐dimethoxy‐1,3,5‐
triazine (3f)
isoxazol‐5‐yl]‐1,3,5‐triazine (3i)
The general procedure was followed using 2‐ethynyl‐4,6‐dimethoxy‐
1,3,5‐triazine 1 (0.44 g, 2.66 mmol, 1 equiv), 3,4,5‐trimethoxybenzaldox-
ime 5i (0.62 g, 2.94 mmol, 1.1 equiv), N‐chlorosuccinimide (0.42 g,
3.2 mmol, 1.2 equiv), KHCO3 (1.34 g, 13.34 mmol, 5 equiv), and ethyl
acetate (20 ml). Yield: 0.40 g (41%); white solid, mp (EtOH) 176–179°C;
Rf = 0.72 (EtOAc/n‐hexane, 1:1). IR (neat): 1587, 1502, 1461, 1418,
The general procedure was followed using 2‐ethynyl‐4,6‐dimethoxy‐
1,3,5‐triazine 1 (0.60 g, 3.64 mmol, 1 equiv), 3,4‐dimethylbenzaldox-
ime 5f (0.6 g, 4.02 mmol, 1.1 equiv), N‐chlorosuccinimide (0.58 g,
4.38 mmol, 1.2 equiv), KHCO3 (1.82 g, 18.18 mmol,
5 equiv),
and ethyl acetate (40 ml). Yield: 0.43 g (38%); beige solid, mp (EtOH)
171–174°C; Rf = 0.74 (EtOAc/n‐hexane, 1:1). IR (neat): 1615, 1541,
1503, 1467, 1446, 1396, 1377, 1343, 1228, 1197, 1148, 1074, 943,
865, 718 cm−1. 1H NMR (400 MHz, CDCl3): δ = 2.36 (s, 3 H, CH3), 2.37
(s, 3 H, CH3), 4.19 (s, 6 H, 2 OCH3), 7.29 (t, J = 6.8 Hz, 1 H, ArH), 7.55
(s, 1 H, ArH), 7.62 (d, J = 7.6 Hz, 1 H, ArH), 7.72 (s, 1 H, ArH). 13C NMR
1388, 1351, 1309, 1236, 1204, 1125, 1041, 1032, 944, 854, 766 cm−1
.
1H NMR (500 MHz, CDCl3): δ = 3.91 (s, 3 H, OCH3), 3.95 (s, 6 H, 2
OCH3), 4.16 (s, 6 H, 2 OCH3), 7.10 (s, 2 H, ArH), 7.51 (s, 1 H, ArH). 13C
NMR (125 MHz, CDCl3): 55.8 (2 CH3), 56.3 (2 CH3), 61.0 (CH3), 104.1
(2 CH), 106.6 (CH), 123.6 (C), 140.0 (C), 153.7 (2 C), 163.0 (C), 165.2 (C),