5
dicarboxylate (2j) Yield: 386 mg (93%); yellow viscous oil;
4.2.5.
Diethyl
1-{[(1-
ACCEPTED MANUSCRIPT
FTIR (film) ν 3287, 3209, 2982, 2936, 1743, 1713, 1542, 1491,
phenylethyl)carbamothioyl]sulfanyl}hydrazine-1,2-
1
dicarboxylate (2d) Yield: 323 mg (87%); yellow viscous oil;
FTIR (film) ν 3374, 3206 s, 3088 w, 3061, 3029, 2981, 2934,
1748, 1717, 1603, 1586, 1533, 1496, 1456, 1404, 1369, 1298,
1247, 1207, 1066, 1043, 699 cm-1; 1H NMR (400 MHz, CDCl3) δ
10.45 (d, J = 7.7 Hz, 1H, NH), 7.43–7.26 (m, 6H), 5.76 (brs, 1H),
4.28–4.17 (m, 4H), 1.65 (d, J = 6.9 Hz, 3H), 1.43–1.11 (m, 6H)
ppm; 13C NMR (101 MHz, CDCl3) δ 191.8, 157.7, 155.4, 141.6,
128.60, 127.5, 126.4, 65.1, 63.5, 54.9, 20.9, 14.4, 14.2 ppm;
HRMS calcd for C15H22N3O4S2 [M+H]+, 372.1052; Found
372.1047.
1293, 1255, 1103, 930, 780 cm-1; H NMR (400 MHz, CDCl3) δ
10.54 (brs, 1H, NH), 7.27–7.23 (m, 1H), 7.06 (brs, 1H, NH),
6.98–6.95 (m, 2H), 6.85–6.82 (m, 1H), 5.06–4.85 (m, 4H), 3.82
(s, 3H), 1.29–1.21 (m, 12H) ppm; 13C NMR (101 MHz, CDCl3) δ
193.7, 159.8, 157.4, 154.7, 137.6, 129.6, 120.3, 113.6, 113.3,
73.7, 71.8, 55.2, 48.9, 21.8, 21.6 ppm; HRMS calcd for
C17H26N3O5S2 [M+H]+, 416.1314; Found 416.1309.
4.2.12.
Diisopropyl
1-
[(propargylcarbamothioyl)sulfanyl]hydrazine-1,2-dicarboxylate
(2k) Yield: 283 mg (85%); white solid; mp 113-116 °C; FTIR
(film) ν 3283, 3191, 2984, 2129, 1706, 1553, 1513, 1298, 1253,
4.2.6. Diethyl 1-{[(3-methoxybenzyl)carbamothioyl]sulfanyl}-
hydrazi-ne-1,2-dicarboxylate (2e)Yield: 298 mg (77%); yellow
viscous oil; FTIR (film) ν 3285, 3212, 2982, 2937, 1747, 1719,
1218, 1102, 906, 665 cm-1; H NMR (400 MHz, CDCl3) δ 10.45
1
(brs, 1H), 7.18 (brs, 1H), 5.06–4.94 (m, 2H), 4.53 (brs, 2H), 2.32
(d, J = 2.6 Hz, 1H), 1.33–1.29 (m, 12H) ppm; 13C NMR (101
MHz, CDCl3) δ 194.5, 157.6, 154.5, 77.18, 73.8, 72.6, 71.9, 34.9,
21.9, 21.7 ppm; HRMS calcd for C12H20N3O4S2 [M+H]+,
334.0895; Found 334.0890.
4.2.13. Diethyl 1-[(octylcarbamothioyl)sulfanyl]hydrazine-1,2-
dicarboxylate (2l) Yield: 212 mg (56%); yellow viscous oil;
FTIR (film) ν 3221, 2981, 2956, 2929, 2870, 2856, 1749, 1720,
1542, 1493, 1369, 1299, 1245, 1207, 1067, 1046, 927, 758 cm-1;
1H NMR (400 MHz, CDCl3) δ 10.07 (brs, 1H, NH), 7.23 (brs,
1H, NH), 4.32–4.24 (m, 4H), 3.76–3.71 (m, 2H), 1.78–1.68 (m,
2H), 1.38–1.25 (m, 16H), 0.91–0.87 (m, 3H) ppm; 13C NMR
(101 MHz, CDCl3) δ 192.4, 157.8, 155.4, 65.1, 63.4, 45.9, 31.8,
29.2, 28.0, 26.8, 22.6, 14.4, 14.3, 14.3, 14.1 ppm; HRMS calcd
for C15H30N3O4S2 [M+H]+, 380.1678; Found 380.1673.
1542, 1492, 1393, 1296, 1247, 1208, 1046, 929, 780 cm-1; H
1
NMR (400 MHz, CDCl3) δ 10.48 (brs, 1H, NH), 7.32–7.23 (m,
2H), 6.96–6.93 (m, 2H), 6.85–6.82 (m, 1H), 5.03–4.71 (brs, 2H),
4.27–4.18 (m, 4H), 3.81 (s, 3H), 1.29–1.23 (m, 6H) ppm; 13C
NMR (101 MHz, CDCl3) δ 193.5, 159.8, 157.7, 155.3, 137.6,
129.6, 120.3, 113.6, 113.3, 65.2, 63.5, 55.2, 48.9, 14.3, 14.2 ppm;
HRMS calcd for C15H22N3O5S2 [M+H]+, 388.1001; Found
388.0997.
4.2.7. Diisopropyl 1-[(butylcarbamothioyl)sulfanyl]hydrazine-
1,2-dicarboxylate (2f) Yield: 253 mg (72%); yellow viscous oil;
FTIR (film) ν 3290, 3213, 2982, 2961, 2935, 2874, 1746, 1715,
1544, 1482, 1294, 1251, 1212, 1103, 1033, 918, 759 cm-1; H
1
NMR (400 MHz, CDCl3) δ 10.13 (brs, 1H, NH), 7.04 (t, J = 10.1
Hz), 5.05–4.96 (m, 2H), 3.76 (brs, 2H), 1.73–1.67 (m, 2H), 1.46–
1.40 (m, 2H), 1.33–1.29 (m, 12H), 0.99–0.95 (m, 3H) ppm; 13C
NMR (101 MHz, CDCl3) δ 192.7, 157.5, 154.7, 73.6, 71.7, 45.6,
30.1, 21.9, 21.7, 20.0, 13.7 ppm; HRMS calcd for C13H26N3O4S2
[M+H]+, 352.1365 ; Found 352.1360.
4.2.14. Diethyl 1-[(diethylcarbamothioyl)sulfanyl]hydrazine-
1,2-dicarboxy-late (2m) Yield: 307 mg (95%); colorless solid;
mp 101-102 °C; FTIR (film) ν 3287, 2980, 2962, 2934, 1742,
1720, 1490, 1473, 1305, 1241, 1205, 1052 cm-1; H NMR (400
1
MHz, CDCl3) δ 8.06–7.92 (brs, 1H, NH), 4.31–4.19 (m, 4H),
3.97 (brs, 2H), 3.53 (brs, 2H), 1.35–1.28 (m, 12H) ppm; 13C
NMR (101 MHz, CDCl3) δ 194.3, 156.0, 154.8, 64.7, 62.1, 49.9,
46.5, 14.4, 14.3, 12.8, 11.5 ppm; HRMS calcd for C11H22N3O4S2
[M+H]+, 324.1052; Found 324.1046.
4.2.8.
Diisopropyl
1-[(prop-2-en-1-
(2g)
ylcarbamothioyl)sulfanyl]hydrazine-1,2-dicarboxylate
Yield: 298 mg (89%); yellow viscous oil; FTIR (film) ν 3285,
3210, 2983, 2936, 1745, 1715, 1540, 1389, 1376, 1294, 1252,
1103, 932, 760 cm-1; H NMR (400 MHz, CDCl3) δ 10.26 (brs,
1
1H, NH), 7.14 (brs, 1H, NH), 5.97–5.88 (m, 1H), 5.33–5.21 (m,
2H), 5.03–4.96 (m, 2H), 4.42–4.34 (brs, 2H), 1.32–1.29 (m, 2H)
ppm; 13C NMR (101 MHz, CDCl3) δ 193.6, 157.5, 154.7, 131.5,
117.8, 73.7, 71.7, 47.7, 21.9, 21.8 ppm; HRMS calcd for
C12H22N3O4S2 [M+H]+, 336.1052; Found 336.1047.
4.2.9. Diisopropyl 1-{[(1-phenylethyl)carbamothioyl]sulfanyl}-
hydrazine-1,2-dicarboxylate (2h) Yield: 371 mg (93%); white
gummy solid; FTIR (film) ν 3286, 3204, 2982, 2091, 1744, 1711,
1533, 1468, 1404, 1388, 1376, 1253, 1210, 1182, 1103, 1064,
1033, 762, 699 cm-1; 1H NMR (400 MHz, CDCl3) δ 10.52 (d, J =
8.1 Hz, 1H, NH), 7.43–7.23 (m, 6H), 5.77 (brs, 1H), 5.05–4.89
(m, 2H), 1.64 (d, J = 7.0 Hz, 3H), 1.38–1.22 (m, 12Hz) ppm; 13C
NMR (101 MHz, CDCl3) δ 191.9, 157.5, 154.8, 141.6, 128.6,
127.5, 126.4, 73.6, 71.7, 54.9, 21.9, 21.9, 21.7, 21.5, 20.9 ppm;
HRMS calcd for C17H26N3O4S2 [M+H]+, 400.1365; Found
400.1360.
4.2.15. Diethyl 1-[(dimethylcarbamothioyl)sulfanyl]hydrazine-
1,2-dicarboxy-late (2n) Yield: 271 mg (92%); colorless solid;
mp 110-113 °C; FTIR (film) ν 3282, 2981, 2934, 1750, 1718,
1
1492, 1475, 1387, 1372, 1307, 1240, 1217, 1053 cm-1; H NMR
(400 MHz, CDCl3) δ 8.00–7.89 (brs, 1H, NH), 4.27–4.17 (m,
4H), 3.49 (s, 3H), 3.23 (s, 3H), 1.32–1.25 ppm; 13C NMR (101
MHz, CDCl3) δ 196.0, 155.9, 154.9, 64.8, 62.2, 45.3, 40.4, 14.4,
14.3 ppm; HRMS calcd for C9H18N3O4S2 [M+H]+, 296.0739;
Found 296.0733.
4.2.16. Diethyl 1-[(dipropylcarbamothioyl)sulfanyl]hydrazine-
1,2-dicar-boxylate (2o) Yield: 333 mg (95%); colorless solid; mp
62-65 °C; FTIR (film) ν 3289, 2967, 2936, 2876, 1745, 1723,
1
1487, 1468, 1299, 1233, 1073, 1052 cm-1; H NMR (400 MHz,
CDCl3) δ 8.04–7.92 (brs, 1H, NH), 4.31–4.18 (m, 4H), 3.84 (brs,
2H), 3.39 (brs, 2H), 1.79–1.73 (m, 4H), 1.32–1.26 (m, 6H),
0.99–0.93 (m, 6H) ppm; 13C NMR (101 MHz, CDCl3) δ 195.6,
156.0, 154.9, 64.6, 62.1, 57.0, 54.0, 21.1, 19.6, 14.4, 14.3, 11.1,
11.1 ppm; HRMS calcd for C13H26N3O4S2 [M+H]+, 352.1365;
Found 352.1361.
4.2.10. Diisopropyl 1-{[(4-methylbenzyl)carbamothioyl]sulfa-
nyl}hydrazine-1,2-dicarboxylate (2i) Yield: 279 mg (70%);
yellow viscous oil; FTIR (film) ν 3286, 3207, 2983, 2935, 1477,
1714, 1541, 1517, 1388, 1376, 1294, 1252, 1213, 1182, 1146,
4.2.17. Diethyl 1-[(azepan-1-ylcarbothioyl)sulfanyl]hydrazine-
1,2-dicar-boxylate (2p) Yield: 311 mg (89%); colorless solid; mp
83-85 °C; FTIR (film) ν 3287, 2982, 2934, 2858, 1751, 1722,
1
1102, 916, 756 cm-1; H NMR (400 MHz, CDCl3) δ 10.51 (brs,
1H, NH), 7.29–7.07 (m, 4H), 7.06 (brs, 1H, NH), 5.09–4.88 (m,
4H), 2.35 (s, 3H), 1.28–1.22 (m, 12H) ppm; 13C NMR (101 MHz,
CDCl3) δ 193.4, 157.4, 154.7, 137.3, 133.1, 129.2, 128.1, 73.7,
71.7, 48.8, 21.8, 21.7, 21.1 ppm; HRMS calcd for
C17H25NaN3O4S2 [M+Na]+, 422.1184; Found 422.1179.
1
1506, 1486, 1476, 1370, 1303, 1225, 1203, 1054 cm-1; H NMR
(400 MHz, CDCl3) δ 8.05–7.94 (brs, 1H, NH), 4.29–4.11 (m,
6H), 3.65 (brs, 2H), 1.91–1.86 (brs 4H), 1.64–1.60 (m, 4H),
1.34–1.28 (m, 6H) ppm; 13C NMR (101 MHz, CDCl3) δ 195.6,
156.1, 155.2, 64.7, 62.1, 55.8, 52.3, 27.6, 26.9, 26.6, 26.0, 14.4,
4.2.11.
Diisopropyl)
1-{[(3-
methoxybenzyl)carbamothioyl]sulfanyl}-hydrazine-1,2-