H
B. Zhou et al.
Paper
Synthesis
13C NMR (101 MHz, CDCl3): δ = 154.5, 151.6, 73.3, 70.8, 65.0, 24.5,
21.9, 21.7, 21.5.
Diethyl 1-(4-Fluorobenzenesulfonyl)hydrazine-1,2-dicarboxylate
(4cb)
HRMS (ESI): m/z [M + H]+ calcd for C12H25N2O6S: 325.1428; found:
Colorless oil; yield: 120 mg (85%); Rf = 0.17 (PE/EtOAc = 5:1, v/v).
1H NMR (400 MHz, CDCl3): δ = 8.30–8.03 (m, 2 H), 7.21 (t, J = 8.6 Hz, 2
H), 7.05 (br s, 1 H), 4.36–4.09 (m, 4 H), 1.32 (t, J = 7.0 Hz, 3 H), 1.21 (t,
J = 7.0 Hz, 3 H).
325.1437.
Diisopropyl 1-(Butanesulfonyl)hydrazine-1,2-dicarboxylate (4ka)
13C NMR (101 MHz, CDCl3): δ = 166.1 (d, J = 257.3 Hz), 154.9, 151.2,
133.7 (d, J = 3.1 Hz), 132.6 (d, J = 9.6 Hz), 115.9 (d, J = 22.9 Hz), 64.5,
63.0, 14.3, 14.0.
Colorless oil; yield: 30 mg (91%); Rf = 0.29 (PE/EtOAc = 5:1, v/v).
1H NMR (400 MHz, CDCl3): δ = 6.95 (br s, 1 H), 5.32–4.77 (m, 2 H),
3.81–3.69 (m, 1 H), 3.72–3.51 (m, 1 H), 1.94–1.87 (m, 2 H), 1.54–1.42
(m, 2 H), 1.43–1.17 (m, 12 H), 0.96 (t, J = 7.3 Hz, 3 H).
HRMS (ESI): m/z [M + Na]+ calcd for C12H15FN2O6SNa: 357.0527;
13C NMR (101 MHz, CDCl3): δ = 154.8, 151.7, 73.1, 71.2, 54.6, 24.5,
found: 357.0518.
21.9, 21.8, 21.6, 21.5, 13.4.
Diethyl 1-[4-(tert-Butylbenzene)sulfonyl]hydrazine-1,2-dicarbox-
ylate (4db)
HRMS (ESI): m/z [M + Na]+ calcd for C12H24N2O6SNa: 347.1247; found:
347.1238.
Colorless oil; yield: 53 mg (82%); Rf = 0.19 (PE/EtOAc = 5:1, v/v).
Diisopropyl 1-(Pyridin-2-ylsulfonyl)hydrazine-1,2-dicarboxylate
(4la)
IR (KBr): 3328, 2965, 2939, 1750, 1594, 1478, 1373, 1233, 1178, 1085,
840 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 8.03 (d, J = 8.3 Hz, 2 H), 7.54 (d, J = 8.7
Hz, 2 H), 7.13 (br s, 1 H), 4.34–4.10 (m, 4 H), 1.36–1.28 (m, 12 H), 1.18
(t, J = 7.1 Hz, 3 H).
13C NMR (101 MHz, CDCl3): δ = 158.2, 154.9, 151.4, 134.8, 129.4,
125.6, 64.3, 62.9, 35.3, 31.0, 14.4, 14.0.
Colorless oil; yield: 35 mg (10%); Rf = 0.50 (PE/EtOAc = 1:1, v/v).
IR (KBr): 3169, 2919, 2850, 1736, 1426, 1382, 1284, 1180, 1076, 956
cm–1
.
1H NMR (400 MHz, CDCl3): δ = 8.68 (d, J = 4.8 Hz, 1 H), 8.30–8.10 (m, 1
H), 7.96 (td, J = 7.8, 1.7 Hz, 1 H), 7.55 (dd, J = 7.7, 4.7 Hz, 1 H), 7.31 (s, 1
H), 5.10–4.93 (m, 1 H), 4.91–4.84 (m, 1 H), 1.27 (d, J = 6.3 Hz, 6 H),
1.15 (d, J = 6.3 Hz, 3 H), 1.07 (d, J = 6.2 Hz, 3 H).
HRMS (ESI): m/z [M + Na]+ calcd for C16H24N2O6SNa: 395.1247; found:
395.1239.
13C NMR (101 MHz, DMSO-d6): δ = 156.1, 154.7, 151.0, 149.8, 138.0,
127.7, 124.1, 73.0, 70.9, 21.8, 21.4.
Diethyl 1-Benzenesulfonylhydrazine-1,2-dicarboxylate (4eb)
HRMS (ESI): m/z [M + H]+ calcd for C13H20N3O6S: 346.1067; found:
Colorless oil; yield: 60 mg (80%); Rf = 0.17 (PE/EtOAc = 5:1, v/v).
1H NMR (400 MHz, CDCl3): δ = 8.13 (d, J = 7.6 Hz, 2 H), 7.64 (t, J = 7.6
Hz, 1 H), 7.54 (t, J = 7.6 Hz, 2 H), 7.14 (br s, 1 H), 4.26–4.17 (m, 4 H),
1.31 (t, J = 6.4 Hz, 3 H), 1.18 (t, J = 6.6 Hz, 3 H).
346.1058.
Diethyl 1-(4-Bromobenzenesulfonyl)hydrazine-1,2-dicarboxylate
(4ab)
13C NMR (101 MHz, CDCl3): δ = 154.8, 151.3, 137.9, 134.2, 129.5,
Colorless oil; yield: 59 mg (91%); Rf = 0.17 (PE/EtOAc = 5:1, v/v).
128.6, 64.4, 62.9, 14.3, 14.0.
HRMS (ESI): m/z [M + Na]+ calcd for C12H16N2O6SNa: 339.0621; found:
339.0629.
IR (KBr): 3338, 2984, 2936, 1745, 1574, 1473, 1375, 1235, 1174, 1069,
821 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 7.99 (d, J = 8.3 Hz, 2 H), 7.68 (d, J = 8.3
Hz, 2 H), 7.04 (br s, 1 H), 4.45–3.95 (m, 4 H), 1.32 (t, J = 7.1 Hz, 3 H),
1.22 (t, J = 7.1 Hz, 3 H).
Diethyl 1-(2-Methylbenzenesulfonyl)hydrazine-1,2-dicarboxylate
(4fb)
13C NMR (101 MHz, CDCl3): δ = 154.3, 151.2, 136.8, 131.9, 131.1,
Colorless oil; yield: 78 mg (82%); Rf = 0.17 (PE/EtOAc = 5:1, v/v).
129.7, 64.6, 63.1, 14.4, 14.0.
HRMS (ESI): m/z [M + Na]+ calcd for C12H15BrN2O6SNa: 416.9726;
IR (KBr): 3294, 2980, 2940, 1736, 1560, 1465, 1363, 1236, 1169, 1046,
752 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 8.14 (d, J = 7.7 Hz, 1 H), 7.52–7.14 (m, 3
H), 6.99 (br s, 1 H), 4.30–4.06 (m, 4 H), 2.61 (s, 3 H), 1.23 (t, J = 7.1 Hz,
3 H), 1.15 (t, J = 7.1 Hz, 3 H).
found: 416.9719.
Diethyl 1-(4-Chlorobenzenesulfonyl)hydrazine-1,2-dicarboxylate
(4bb)
13C NMR (101 MHz, CDCl3): δ = 154.8, 151.6, 136.5, 134.0, 132.5,
Colorless oil; yield: 58 mg (88%); Rf = 0.17 (PE/EtOAc = 5:1, v/v).
131.6, 130.9, 126.1, 64.4, 62.9, 20.6, 14.3, 14.0.
HRMS (ESI): m/z [M + Na]+ calcd for C13H18N2O6SNa: 353.0778; found:
353.0769.
IR (KBr): 3327, 2984, 2940, 1742, 1584, 1477, 1376, 1236, 1174, 1065,
829 cm–1
.
1H NMR (400 MHz, CDCl3): δ = 8.06 (d, J = 8.3 Hz, 2 H), 7.51 (d, J = 8.4
Hz, 2 H), 7.09 (br s, 1 H), 4.39–4.03 (m, 4 H), 1.32 (t, J = 7.1 Hz, 3 H),
1.21 (t, J = 7.1 Hz, 3 H).
Acknowledgment
13C NMR (101 MHz, CDCl3): δ = 154.8, 151.2, 141.0, 136.3, 131.1,
This work was supported in part by the National Basic Research Pro-
gram of China (No. 2013CB328905) and the National Natural Science
Foundation of China (Nos. 21372025 and 21572017).
128.9, 64.6, 63.1, 14.3, 14.0.
HRMS (ESI): m/z [M + Na]+ calcd for C12H15ClN2O6SNa: 373.0232;
found: 373.0239.
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 48, A–I