Chemistry of Heterocyclic Compounds 2019, 55(7), 665–671
δ, ppm: 35.5 (CH2); 73.7 (C–OH); 120.5 (2CH Ar); 123.9
2965 (CH), 1670 (С=О), 1597, 1511, 1243, 1179, 1066,
1026, 828, 756. H NMR spectrum (DMSO-d6), δ, ppm
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(CH Ar); 126.7 (2CH Ar); 128.6 (CH Ar); 128.7 (2CH Ar);
129.1 (2CH Ar); 138.8 (C Ar); 144.1 (C Ar); 144.2 (C);
161.3 (C=O). Found, m/z: 314.0955 [M+H]+. C16H16N3O2S.
Calculated, m/z: 314.0958.
(J, Hz): 2.85 (1Н, AB system, J = 12.1, CH2); 3.49 (1Н,
AB system, J = 12.1, CH2); 3.73 (3H, s, OCH3); 3.79 (3H,
s, OCH3); 4.22 (1Н, br. s, OH); 6.88 (2Н, d, J = 8.8, H Ar);
7.01 (1Н, ddd, J = 7.7, J = 7.3, J = 1.3, H Ar); 7.07 (1Н,
dd, J = 7.7, J = 1.3, H Ar); 7.37 (1Н, td, J = 7.7, J = 1.8,
H Ar); 7.63 (2Н, d, J = 8.8, H Ar); 7.70 (1Н, dd, J = 7.7,
J = 1.8, H Ar); 8.56 (1Н, br. s, NH); 9.55 (1Н, br. s, NH).
13C NMR spectrum (DMSO-d6), δ, ppm: 30.8 (CH2); 55.7
(OCH3); 56.2 (OCH3); 74.8 (C–OH); 112.8 (CH Ar); 114.2
(2CH Ar); 120.5 (CH Ar); 121.9 (2CH Ar); 126.4 (C Ar);
128.7 (CH Ar); 130.4 (C Ar); 130.5 (CH Ar); 132.1 (C);
155.8 (C Ar); 157.3 (C Ar); 161.2 (C=O). Found, m/z:
374.1163 [M+H]+. C18H20N3O4S. Calculated, m/z: 374.1169.
5-Hydroxy-5-(2-methoxyphenyl)-N-(2-nitrophenyl)-
5-Hydroxy-N-(4-methoxyphenyl)-5-phenyl-5,6-dihydro-
4H-1,3,4-thiadiazine-2-carboxamide (5h). Yield 86 mg
(89%), pale-yellow powder, mp 116–118°C (decomp.).
IR spectrum, ν, cm–1: 3501 (OH), 3365 (NH), 3321 (NH),
2942 (CH), 1646 (С=О), 1542, 1468, 1237, 1069, 1031,
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819, 701, 626. H NMR spectrum (DMSO-d6), δ, ppm
(J, Hz): 2.97 (1Н, AB system, J = 12.1, CH2); 3.09 (1Н,
AB system, J = 12.1, CH2); 3.73 (3H, s, OCH3); 6.29 (1Н,
br. s, OH); 6.89 (2H, d, J = 8.8, H Ar); 7.34–7.47 (3Н, m,
H Ar); 7.56 (2Н, d, J = 7.3, H Ar); 7.63 (2Н, d, J = 8.8,
H Ar); 8.45 (1Н, br. s, NH); 9.61 (1Н, br. s, NH). 13C NMR
spectrum (DMSO-d6), δ, ppm: 35.6 (CH2); 55.7 (OCH3);
73.7 (C–OH); 114.3 (2CH Ar); 122.0 (CH Ar); 122.1
(2CH Ar); 126.7 (2CH Ar); 128.6 (C Ar); 128.7 (2CH Ar);
131.9 (C Ar); 144.2 (C); 155.9 (C Ar); 160.9 (C=O). Found, m/z:
344.1060 [M+H]+. C17H18N3O3S. Calculated, m/z: 344.1063.
5-Hydroxy-N-(2-nitrophenyl)-5-phenyl-5,6-dihydro-
4H-1,3,4-thiadiazine-2-carboxamide (5i). Yield 98 mg
(98%), pale-yellow powder, mp 102–104°C (decomp.).
IR spectrum, ν, cm–1: 3475 (OH), 3310 (NH), 2943 (CH),
1685 (С=О), 1581, 1501, 1434, 1342, 1273, 1052, 740,
5,6-dihydro-4H-1,3,4-thiadiazine-2-carboxamide
(5l).
Yield 103 mg (95%), pale-yellow powder, mp 169–171°C
(decomp.). IR spectrum, ν, cm–1: 3447 (OH), 3384 (NH),
3299 (NH), 2833 (CH), 1669 (С=О), 1582, 1502, 1435,
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1342, 1278, 1030, 951, 826, 757, 581. H NMR spectrum
(DMSO-d6), δ, ppm (J, Hz): 2.85 (1Н, AB system, J = 11.9,
CH2); 3.44 (1Н, AB system, J = 11.9, CH2); 3.79 (3H, s,
OCH3); 6.30 (1Н, br. s, OH); 7.02 (1Н, ddd, J = 7.7,
J = 7.3, J = 1.3, H Ar); 7.08 (1Н, dd, J = 7.7, J = 1.3, H Ar),
7.30 (1Н, ddd, J = 8.4, J = 8.4, J = 1.5, H Ar); 7.38 (1Н,
ddd, J = 7.7, J = 7.3, J = 1.8, H Ar); 7.69 (1Н, dd, J = 7.7,
J = 1.8, H Ar); 7.79 (1Н, ddd, J = 8.8, J = 8.4, J = 1.5,
H Ar); 8.19 (1Н, dd, J = 8.8, J = 1.5, H Ar); 8.58 (1Н, dd,
J = 8.4, J = 1.5, H Ar); 9.21 (1Н, br. s, NH); 11.30 (1Н,
br. s, NH). 13C NMR spectrum (DMSO-d6), δ, ppm: 30.7
(CH2); 56.2 (OCH3); 72.9 (C–OH); 112.8 (CH Ar); 118.3
(C Ar); 120.6 (CH Ar); 123.8 (CH Ar); 124.9 (CH Ar);
126.3 (CH Ar); 128.7 (CH Ar); 130.6 (CH Ar); 131.2
(C Ar); 132.2 (C Ar); 136.2 (CH Ar); 147.6 (C); 157.3
(C Ar); 161.7 (C=O). Found, m/z: 389.0906 [M+H]+.
C17H17N4O5S. Calculated, m/z: 389.0914.
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690. H NMR spectrum (DMSO-d6), δ, ppm (J, Hz): 3.00
(1Н, AB system, J = 12.1, CH2); 3.08 (1Н, AB system,
J = 12.1, CH2); 6.51 (1Н, br. s, OH); 7.26–7.48 (4Н, m, H Ar);
7.56 (2Н, d, J = 6.6, H Ar); 7.79 (1Н, ddd, J = 8.7, J = 8.3,
J = 1.8, H Ar); 8.19 (1Н, dd, J = 8.3, J = 1.8, H Ar); 8.57
(1Н, dd, J = 8.7, J = 1.8, H Ar); 9.17 (1Н, br. s, NH); 11.32
(1Н, br. s, NH). 13C NMR spectrum (DMSO-d6), δ, ppm:
35.0 (CH2); 74.1 (C–OH); 122.4 (CH Ar); 124.1 (CH Ar);
126.3 (CH Ar); 126.7 (2CH Ar); 128.6 (CH Ar); 128.7
(2CH Ar, C Ar); 133.9 (C Ar); 136.2 (CH Ar); 137.9 (C Ar);
143.7 (C); 161.5 (C=O). Found, m/z: 359.0805 [M+H]+.
C16H15N4O4S. Calculated, m/z: 359.0809.
N-(2-Chloropyridin-3-yl)-5-hydroxy-5-(2-methoxyphenyl)-
5,6-dihydro-4H-1,3,4-thiadiazine-2-carboxamide (5m).
Yield 104 mg (98%), pale-yellow powder, mp 138–140°C
(decomp.). IR spectrum, ν, cm–1: 3343 (NH), 2944 (CH),
1683 (С=О), 1514, 1394, 1242, 1089, 1026, 802,
756. NMR spectrum (DMSO-d6), δ, ppm (J, Hz): 2.85 (1Н,
AB system, J = 12.3, CH2); 3.44 (1Н, AB system, J = 12.3,
CH2); 3.79 (3H, s, OCH3); 6.29 (1Н, br. s, OH); 7.01 (1Н,
ddd, J = 7.7, J = 7.3, J = 1.3, H Ar); 7.08 (1Н, dd, J = 7.7,
J = 1.3, H Ar); 7.38 (1Н, ddd, J = 8.1, J = 7.3, J = 1.3,
H Ar); 7.48 (1Н, dd, J = 8.1, J = 4.8, H Ar); 7.70 (1Н, dd,
J = 8.1, J = 1.3, H Ar); 8.17 (1Н, dd, J = 4.8, J = 1.5,
H Ar); 8.55 (1Н, dd, J = 8.1, J = 1.5, H Ar); 9.12 (1Н, br. s,
NH); 9.40 (1Н, br. s, NH). 13C NMR spectrum (DMSO-d6),
δ, ppm: 30.2 (CH2); 56.2 (OCH3); 74.9 (C–OH); 112.8
(CH Ar); 120.6 (CH Ar); 124.4 (CH Ar); 124.5 (C Ar);
128.7 (CH Ar); 129.9 (CH Ar); 130.6 (CH Ar); 132.1
(C Ar); 143.4 (C Ar); 144.5 (CH Ar); 145.8 (C); 157.3
(C Ar); 161.4 (C=O). Found, m/z: 381.0596 [M+H]+.
C16H16ClN4O3S. Calculated, m/z: 381.0597.
5-Hydroxy-5-(2-methoxyphenyl)-N-phenyl-5,6-dihydro-
4H-1,3,4-thiadiazine-2-carboxamide (5j). Yield 88 mg (92%),
pale-yellow powder, mp 112–115°C (decomp.). IR spectrum,
ν, cm–1: 3360 (OH), 3306 (NH), 2942 (CH), 1670 (С=О),
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1598, 1533, 1444, 1315, 1246, 1024, 877, 752. H NMR
spectrum (DMSO-d6), δ, ppm (J, Hz): 2.86 (1Н, AB system,
J = 12.1, CH2); 3.48 (1Н, AB system, J = 12.1, CH2); 3.79
(3H, s, OCH3); 6.15 (1Н, br. s, OH); 6.97–7.18 (3Н, m,
H Ar); 7.26–7.43 (3Н, m, H Ar); 7.52–7.64 (1Н, m, H Ar);
7.71 (1Н, dd, J = 8.1, J = 7.7, H Ar); 7.85 (1Н, d, J = 8.1,
H Ar); 8.60 (1Н, br. s, NH); 9.65 (1Н, br. s, NH). 13C NMR
spectrum (DMSO-d6), δ, ppm: 30.7 (CH2); 56.2 (OCH3);
74.8 (C–OH); 112.8 (CH Ar); 120.3 (CH Ar); 120.4
(CH Ar); 120.6 (CH Ar); 123.8 (CH Ar); 128.7 (CH Ar);
129.1 (2CH Ar); 130.3 (C Ar); 130.5 (CH Ar); 133.1 (C Ar);
138.9 (C); 157.3 (C Ar); 161.5 (C=O). Found, m/z: 344.1059
[M+H]+. C17H18N3O3S. Calculated, m/z: 344.1063.
5-Hydroxy-5-(2-methoxyphenyl)-N-(4-methoxyphenyl)-
5,6-dihydro-4H-1,3,4-thiadiazine-2-carboxamide (5k).
Yield 98 mg (94%), pale-yellow powder, mp 80–82°C
(decomp.). IR spectrum, ν, cm–1: 3475 (OH), 3358 (NH),
Synthesis of 5-substituted-6H-1,3,4-thiadiazine-2-carb-
oxamides 6a–d (General method). Oxamic acid thio-
669