R.P. Modh et al.: Coumarinyl-triazine derivatives as antimicrobial agentꢀꢂꢁꢁꢁꢀ5
(
1C, s-triazine C-S mercapto oxadiazole), 116.4, 116.5, 128.4, 129.2, 135.5, 3-(5-(4-Morpholino-6-(p - to lylamino)-1,3,5-triazin-2-ylthio)-
143.6 (6C, aromatic amine), 48.2, 54.3, 62.6, 63.4 (4C, morpholine); MS: 1,3,4-oxadiazole-2-yl)-2H-chromene-2-one (6g)ꢁYield 59%; mp
+
-
1
m/z 535 (M ); mp 141–143°C, Anal. Calcd for C H N O SCl (535.96): C, 131–133°C (from ethanol); IR (cm ): 1705 (C=O), 1559 (C=N-), 825
5
24
18
7
4
3.78; H, 3.39; N, 18.29. Found: C, 53.76; H, 3.37; N, 18.28.
(C=N), 1210 (C-O-C), 3410, 1675 (NH), 1032 (C-O-C), 2955 (CH), 1470
1
(
CH); H NMR: δ 9.18 (s, 1H, NH), 8.42 (s, 1H, Ar-H), 6.8–8.04 (m, 4H,
Ar-H), 7.24 (d, 2H, J = 7.5 Hz, Ar-H), 7.09 (d, 2H, J = 7.5 Hz, Ar-H), 3.32
3
1
-(5-(4-(3-Chloroanilino)-6-morpholino-1,3,5-triazin-2-ylthio)-
(
t, 4H, J = 7.1 Hz, -CH ), 3.10 (t, 4H, J = 7.1 Hz, CH ), 1.90 (s, 3H, CH );
,3,4-oxadiazole-2-yl)-2H-chromene-2-one (6c)ꢁYield 55%; mp
2 2 3
C NMR: δ 161.2 (C=O), 146 (CH=C, coumarin), 116, 124.9, 126, 127, 128,
1
3
-1
1
30–134°C (from ethanol); IR (cm ): 1705 (C=O), 1520 (C=N), 825
1
29.2, 153.6 (7C, coumarin), 161.4, 163.2 (2C, C-O-C), 178.4 (C-N, mor-
(
C=N), 1215 (C-O-C, oxadiazole), 3410, 1675 (NH), 1002 (C-O-C, ether),
1
pholine), 166.8 (C-NH, amino linkage), 182.2 (C-S), 117.4, 117.6, 122.3,
2
955 (CH), 1470 (CH); H NMR: δ 9.18 (s, 1H, NH), 8.42 (s, 1H, Ar-H),
1
26.4, 126.5, 138.6 (6C, aromatic amine), 47.2, 52.4, 60.6, 62.1 (4C, mor-
6
.81–7.90 (m, 8H, Ar-H), 3.11 (t, 4H, J = 7.1 Hz, CH ), 3.32 (t, 4H, J =
2
+
1
3
pholine), 23.4 (CH ); MS: m/z 515 (M ). Anal. Calcd for C H N O S
7
.1 Hz, CH ); C NMR: δ 161.2 (C=O, coumarin), 146 (CH=C, coumarin),
3
25 21
7
4
2
(
515.94): C, 58.24; H, 4.11; N, 19.02. Found: C, 58.24; H, 4.10; N, 18.89.
1
16, 125, 126, 127, 128.2, 129.1, 152.6 (7C, coumarin), 161.4, 164.2 (2C, C-
O-C, oxadiazole), 178.4 (C-N, morpholine), 166.7 (C-NH, amino linka-
ge), 182.2 (C-S), 117.4, 117.6, 129.4, 130.3, 135.5, 143.6 (6C, aromatic ami- 3-(5-(4-(2-Methoxyanilino)-6-morpholino-1,3,5-triazin-2-ylthio)-
+
ne), 48.4, 54.5, 62.2, 63.7 (4C, morpholine); MS: m/z 535 (M ). Anal. 1,3,4-oxadiazole-2-yl)-2H-chromene-2-one (6h)ꢁYield 59%; mp
-1
Calcd for C H N O SCl (535.96): C, 53.78; H, 3.39; N, 18.29. Found: C, 132–134°C (from ethanol); IR (cm ): 1710 (C=O), 1540 (C=N), 825 (C=N),
24
18
7
4
1
5
3.76; H, 3.37; N, 18.27.
1210 (C-O-C), 3410, 1675 (NH), 1032 (C-O-C), 2955 (CH), 1470 (CH); H
NMR: δ 9.18 (s, 1H, NH), 8.42 (s, 1H, Ar-H), 7.42–7.84 (m, 4H, Ar-H),
6
.52–6.85 (m, 4H, Ar-H), 3.34 (s, 3H of OCH ), 3.32 (t, 4H, J = 7.1 Hz,
3
1
-(5-(4-(4-Chloroanilino)-6-morpholino-1,3,5-triazin-2-ylthio)-
3
13
CH ), 3.12 (t, 4H, J = 7.1 Hz, CH ); C NMR: δ 161.2 (C=O, coumarin),
,3,4-oxadiazole-2-yl)-2H-chromene-2-one (6d)ꢁYield 64%; mp
2
2
-1
146 (CH=C, coumarin), 116, 125.2, 126, 127, 128.6, 129.5, 153.6 (7C, cou-
marin), 161.4, 163.2 (2C, C-O-C oxadiazole), 178.4 (C-N, morpholine),
167 (C-NH, amino linkage), 182.2 (C-S), 117.4, 117.6, 122.3, 126.4, 126.5,
1
60–164°C (from ethanol); IR (cm ): 1700 (C=O), 1500 (C=N), 825
(
C=N), 1210 (C-O-C oxadiazole), 3406 (NH), 1671 (NH), 1032 (C-O-C,
1
ether), 2960 (CH), 1475 (CH); H NMR: δ 9.10 (s, 1H, NH), 8.20 (s, 1H, Ar-
1
38.6 (6C, aromatic amine) 45.3, 50.2, 54.8, 64.7 (4C, morpholine), 58.2
(OCH ); MS: m/z 531 (M ). Anal. Calcd for C H N O S (515.94): C, 58.24;
H), 7.45–8.04 (m, 4H, Ar-H), 7.42 (d, 2H, J = 7.5 Hz, Ar-H), 7.24 (d, 2H, J =
+
13
7.5 Hz, Ar-H), 3.32 (t, 4H, J = 7.1 Hz, -CH ), 3.11 (t, 4H, J = 7.1 Hz, CH ); C
3
25 21
7
4
2
2
H, 4.11; N, 19.02; S, 6.03. Found: C, 58.24; H, 4.10; N, 18.99; S, 6.06.
NMR: δ 161.2 (C=O), 146 (CH=C, coumarin), 116, 124.9, 126, 127, 128.1,
29.4, 153.6 (7C, coumarin), 161.4, 163.2 (2C, C-O-C oxadiazole), 178.4
C-N, morpholine), 166.5 (C-NH, amino linkage), 182.2 (C-S), 117.4, 3-(5-(4-(4-Methoxyanilino)-6-morpholino-1,3,5-triazin-2-ylthio)-
17.6, 122.3, 127.5, 127.4, 139.6 (6C, aromatic amine), 47, 48.4, 59.4, 63.5 1,3,4-oxadiazole-2-yl)-2H-chromene-2-one (6i)ꢁYield 62%; mp
1
(
1
+
-1
(
(
4C, morpholine); MS: m/z 535 (M ). Anal. Calcd for C H ClN O S 154–157°C (from ethanol); IR (cm ): 1725 (C=O), 1540 (C=N), 825 (C=N),
24
18
7
4
1
535.96): C, 53.78; H, 3.39; N, 18.29. Found: C, 53.77; H, 3.41; N, 18.26.
1210 (C-O-C), 3410, 1675 (NH), 1032 (C-O-C), 2955 (CH), 1470 (CH); H
NMR: δ 9.21 (s, 1H, NH), 8.39 (s, 1H, Ar-H), 7.42–8.04 (m, 4H, Ar-H), 7.24
(
7
d, 2H, J = 7.5 Hz, Ar-H), 7.09 (d, 2H, J = 7.5 Hz, Ar-H), 3.09 (t, 4H, J =
3
1
-(5-(4-Morpholino-6-(o-tolylamino)-1,3,5-triazin-2-ylthio)-
13
.1 Hz, -CH ), 3.30 (t, 4H, J = 7.1 Hz, CH ), 3.83 (s, 3H, OCH ); C NMR:
,3,4-oxadiazole-2-yl)-2H-chromene-2-one (6e)ꢁYield 62%; mp
2
2
3
-
1
δ 161.2 (C=O, coumarin), 146 (CH=C), 116, 124.8, 126, 127, 128.6, 129.4,
53.6 (7C, coumarin), 161.4, 163.2 (2C, C-O-C), 178.4 (C-N, morpholine),
1
81–185°C (from ethanol); IR (cm ): 1725 (C=O), 1500 (C=N), 825
1
(
C=N), 1210 (C-O-C), 3410, 1675 (NH), 1122 (C-O-C), 2955 (CH), 1470
1
166.6 (C-NH, amino linkage), 182.2 (C-S), 117.4, 117.6, 122.3, 126.4, 126.5,
(
CH); H NMR: δ 9.05 (s, 1H, NH), 8.42 (s, 1H, Ar-H), 6.70–7.79 (m, 8H,
1
38.6 (6C, aromatic amine), 45.6, 50.6, 54.2, 64.4 (4C, morpholine),
Ar-H), 3.11 (t, 4H, J = 7.1 Hz, CH ), 3.29 (t, 4H, J = 7.1 Hz, CH ), 1.93 (s,
2
2
+
1
3
58.23 (OCH ); MS: m/z 501 (M ). Anal. Calcd for C H N O S: C, 56.49;
3
H, CH ); C NMR: δ 161.2 (C=O), 146 (CH=C), 116, 125.3, 126, 127, 128.6,
29.8, 153.6 (7C, coumarin), 161.4, 163.2 (2C, C-O-C oxadiazole), 178.4
3
25 21
7
5
3
H, 3.98; N, 18.45; S, 6.03. Found: C, 56.44; H, 3.99; N, 18.40; S, 6.00.
1
(
C-N, morpholine), 166.1 (C-NH, amino linkage), 182.2 (C-S),114.4,
1
14.3, 122.3, 126.4, 126.5, 139.3 (6C, aromatic amine), 46.4, 49.3, 58.4, 3-(5-(4-(2-Chloro-4-nitroanilino)-6-morpholino-1,3,5-triazin-
+
6
3.3 (4C, morpholine), 23.2 (CH ); MS: m/z 515 (M ). Anal. Calcd for 2-ylthio)-1,3,4-oxadiazole-2-yl)-2H-chromene-2-one (6j)ꢁYield
3
-1
C H N O S (515.54): C, 58.24; H, 4.11; N, 19.02. Found: C, 58.21; H, 43%; mp 152–156°C (from ethanol); IR (cm ): 1700 (C=O), 1549 (C=N),
4
2
5
21
7
4
.09; N, 19.04.
820 (C=N), 1210 (C-O-C), 3400, 1670 (NH), 1232 (C-O-C), 2895 (CH),
1
1
470 (CH); H NMR: δ 9.05 (s, 1H, NH), 6.83 (s, 1H, Ar-H), 7.2–8.05
(
m, 5H, Ar-H), 8.10 (d, 2H, J = 7.1 Hz, Ar-H), 3.20 (t, 4H, J = 7.1 Hz,
3
1
-(5-(4-Morpholino-6-(m - to lylamino)-1,3,5-triazin-2-ylthio)-
1
3
CH ), 3.32 (t, 4H, J = 7.1 Hz, CH ); C NMR: δ 161.2 (C=O, coumarin),
,3,4-oxadiazole-2-yl)-2H-chromene-2-one (6f)ꢁYield 68%; mp
2
2
-1
146 (CH=C, coumarin), 116, 125.2, 126, 127, 128.1, 129.6, 153.6 (7C, cou-
marin), 161.4, 163.2 (2C, C-O-C), 178.4 (C-N, morpholine), 166.6 (C-NH,
amino linkage), 182.2 (C-S), 117.4, 120.6, 122.3, 126.4, 126.5, 138.6 (6C,
1
42–144°C (from ethanol); IR (cm ): 1725 (C=O), 1540 (C=N), 825
(
C=N), 1210 (C-O-C), 3410, 1675 (NH), 1032 (C-O-C), 2955 (CH), 1470
1
(
CH); H NMR: δ 9.18 (s, 1H, NH), 8.42 (s, 1H, Ar-H), 6.59–7.85 (m, 8H,
aromatic amine), 48.3, 50.2, 60.2, 63.4 (4C, morpholine); MS: m/z 580
Ar-H), 3.12 (t, 4H, J = 7.1 Hz, CH ), 3.32 (t, 4H, J = 7.1 Hz, CH ), 1.90 (s,
2
2
+
1
3
(M ). Anal. Calcd for C H ClN O S (580.96): C, 49.62; H, 2.95; N, 19.29.
3
H, CH ); C NMR: δ 161.2 (C=O), 146 (CH=C), 116, 125.2, 126, 127, 128.4,
24 17
8
6
3
Found: C, 49.65; H, 2.93; N, 19.32.
1
29.1, 153.6 (7C, coumarin), 161.4, 163.2 (2C, C-O-C), 178.4 (C-N, mor-
pholine), 166.4 (C-NH, amino linkage), 182.2 (C-S), 117.4, 117.6, 122.3,
1
26.4, 126.5, 138.6 (6C, aromatic amine), 48.3, 54.3, 58.5, 64.2 (4C, 3-(5-(4-Morpholino-6-(3-nitroanilino)-1,3,5-triazin-2-ylthio)-
+
morpholine), 23.4 (CH ); MS: m/z 515 (M ). Anal. Calcd for C H N O S 1,3,4-oxadiazole-2-yl)-2H-chromene-2-one (6k)ꢁYield 61%; mp
3
25 21
7
4
-1
(
515.54): C, 58.24; H, 4.11; N, 19.02. Found: C, 58.26; H, 4.13; N, 19.1.
152–154°C (from ethanol); IR (cm ): 1705 (C=O), 1510 (C=N-), 820
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