6-(Furan-2-ylmethylene)-4-phenyl-2-phenylaminocarbonyl-1,3,4-thiadiazin-5-one (5j). IR spectrum, ν,
1
cm-1: 3260 (N–H), 1676 (lactam C=O), 1650 (amide C=O), 1208 (C–S). H NMR spectrum, δ, ppm: 9.15 (1H, s,
NH); 7.72-7.16 (13H, m, H Ar); 6.13 (1H, s, CH). 13C NMR spectrum, δ, ppm: 160.6 (lactam C=O); 158.2 (amide
C=O); 144.7 (C=N); 141.3; 138.9; 137.9; 135.2; 134.8; 130.4; 128.7; 128.5; 127.6; 126.5; 124.3; 123.3; 114.4 (12
arom. carbons and C-6); 110.9 (=CH).
4-Phenyl-2-phenylaminocarbonyl-6-(thiophen-2-ylmethylene)-1,3,4-thiadiazin-5-one (5k). IR spectrum,
ν, cm–1: 3255 (N−H), 1678 (lactam C=O), 1652 (amide C=O), 1202 (C−S). 1H NMR spectrum, δ, ppm: 9.17 (1H, s,
NH); 7.76-7.20 (13H, m, H Ar); 6.10 (1H, s, CH). 13C NMR spectrum, δ, ppm: 160.8 (lactam C=O); 158.5 (amide
C=O); 145.1 (C=N); 141.5; 138.2; 134.7; 131.4; 129.1; 128.8; 128.0; 127.8; 127.2; 124.5; 121.8; 114.7 (12 arom.
carbons and C-6); 110.3 (=CH).
6-Benzylidene-4-(4-chlorophenyl)-2-phenylaminocarbonyl-1,3,4-thiadiazin-5-one (5l). IR spectrum, ν,
1
cm–1: 3257 (N−H), 1680 (lactam C=O), 1660 (amide C=O), 1207 (C−S). H NMR spectrum, δ, ppm: 9.33 (1H, s,
NH); 7.50-7.05 (14H, m, H Ar); 6.12 (1H, s, CH). 13C NMR spectrum, δ, ppm: 160.7 (lactam C=O); 157.9 (amide
C=O); 143.9 (C=N); 141.0; 139.0; 138.6; 135.0; 130.4; 129.1; 128.6; 128.3; 126.4; 124.2; 123.3; 120.1; 115.8 (12
arom. carbons and C-6); 111.3 (=CH).
4-(4-Chlorophenyl)-6-(furan-2-ylmethylene)-2-phenylaminocarbonyl-1,3,4-thia- diazin-5-one (5m). IR
1
spectrum, ν, cm–1: 3265 (N−H), 1682 (lactam C=O), 1665 (amide C=O), 1205 (C−S). H NMR spectrum, δ, ppm:
13
9.25 (1H, s, NH); 7.64-7.13 (12H, m, H Ar); 6.16 (1H, s, CH). C NMR spectrum, δ, ppm: 160.1 (lactam C=O);
157.7 (amide C=O); 144.5 (C=N); 140.2; 139.5; 138.9; 135.2; 130.5; 128.7; 128.5; 127.7; 125.8; 124.4; 123.2;
120.2; 116.5 (12 arom. carbons and C-6); 110.9 (=CH).
4-(4-Chlorophenyl)-2-phenylaminocarbonyl-6-(thiophen-2-ylmethylene)-1,3,4-thiadiazin-5-one (5n).
IR spectrum, ν, cm–1: 3258 (N−H), 1679 (lactam C=O), 1660 (amide C=O), 1204 (C−S). 1H NMR spectrum, δ, ppm:
13
9.23 (1H, s, NH); 7.68-7.20 (12H, m, H Ar); 6.14 (1H, s, CH). C NMR spectrum, δ, ppm: 160.2 (lactam C=O);
158.1 (amide C=O); 144.1 (C=N); 140.6; 139.6; 138.6; 135.0; 130.2; 129.6; 128.9; 128.2; 127.9; 124.2; 123.0;
120.8; 116.8 (arom. carbons and C-6); 110.5 (=CH).
6-Benzylidene-4-(4-bromophenyl)-2-phenylaminocarbonyl-1,3,4-thiadiazin-5-one (5o). IR spectrum, ν,
1
cm–1: 3246 (N−H), 1682 (lactam C=O), 1650 (amide C=O), 1211 (C−S). H NMR spectrum, δ, ppm: 9.19 (1H, s,
NH); 7.49-7.11 (14H, m, H Ar); 6.16 (1H, s, CH). 13C NMR spectrum, δ, ppm: 160.8 (lactam C=O); 158.0 (amide
C=O); 144.7 (C=N); 141.0; 139.9; 138.4; 137.5; 135.1; 131.4; 128.8; 127.8; 127.6; 125.8; 124.5; 121.1; 118.5 (12
arom. carbons and C-6); 111.1 (=CH).
4-(4-Bromophenyl)-2-phenylaminocarbonyl-6-(thiophen-2-ylmethylene)-1,3,4-thiadiazin-5-one (5p).
IR spectrum, ν, cm–1: 3249 (N−H), 1683 (lactam C=O), 1655 (amide C=O), 1210 (C−S). 1H NMR spectrum, δ, ppm:
13
9.26 (1H, s, NH); 7.51-7.13 (12H, m, H Ar); 6.15 (1H, s, CH). C NMR spectrum, δ, ppm: 160.9 (lactam C=O);
158.2 (amide C=O); 144.3 (C=N); 141.3; 139.1; 138.6; 137.7; 135.3; 131.2; 129.1; 128.4; 127.1; 126.6; 124.1;
120.9; 118.4 (12 arom. carbons and C-6); 110.3 (=CH).
4-(4-Fluorophenyl)-6-(furan-2-ylmethylene)-2-phenylaminocarbonyl-1,3,4-thiadiazin-5-one (5q). IR
1
spectrum, ν, cm–1: 3245 (N−H), 1681 (lactam C=O), 1650 (amide C=O), 1213 (C−S). H NMR spectrum, δ, ppm:
13
9.12 (1H, s, NH); 7.48-7.14 (12H, m, H Ar); 6.18 (1H, s, CH). C NMR spectrum, δ, ppm: 160.7 (lactam C=O);
158.1 (amide C=O); 144.1 (C=N); 140.6; 139.4; 138.4; 135.5; 132.2; 129.3; 128.7; 128.2; 127.4; 125.4; 120.2;
116.6; 115.7 (12 arom. carbons and C-6); 110.2 (=CH).
6-Benzylidene-4-(4-chlorophenyl)-2-furoyl-1,3,4-thiadiazin-5-one (5r). IR spectrum, ν, cm–1: 1682
(lactam C=O), 1660 (C=O), 1213 (C−S). 1H NMR spectrum, δ, ppm: 7.84-7.16 (12H, m, H Ar); 6.20 (1H, s, CH).
13C NMR spectrum, δ, ppm: 173.5 (C=O); 161.3 (lactam C=O); 145.3 (C=N); 142.9; 139.7; 134.9; 130.4; 129.8;
129.0; 128.9; 128.6; 127.3; 125.1; 123.7; 120.6; 115.0 (12 arom. carbons and C-6); 111.3 (=CH).
4-(4-Chlorophenyl)-6-(furan-2-ylmethylene)-2-(2-furoyl)-1,3,4-thiadiazin-5-one (5s). IR spectrum, ν,
1
cm–1: 1682 (lactam C=O), 1665 (C=O), 1215 (C−S). H NMR spectrum, δ, ppm: 7.82-7.14 (10H, m, H Ar); 6.21
13
(1H, s, CH). C NMR spectrum, δ, ppm: 173.4 (C=O); 161.0 (lactam C=O); 145.7 (C=N); 142.3; 139.6; 135.2;
132.2; 130.9; 129.8; 129.1; 128.8; 127.6; 125.3; 123.7; 120.8; 114.9 (12 arom. carbons and C-6); 110.7 (=CH).
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