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Russ. Chem. Bull., Int. Ed., Vol. 70, No. 3, March, 2021
(DMSO-d6), δ: 2.36 (s, 3 H, CH3); 2.61—3.01 (m, 2 H,
HCCH2CO); 3.40—3.74 (m, 2 H, CHCH2N); 4.02—4.24 (m, 1 H,
PhCH); 4.30 (d, 2 H, CH2NH, 3J = 7.89 Hz); 5.50—5.71 (m, 1 H,
NH); 7.07—7.40 (m, 7 H, C6H5, CHС(CH3)CH); 7.74 (d, 2 H,
CHС(SO2)CH, 3J = 7.95 Hz). 13C NMR (DMSO-d6), δ: 21.41
(CH3), 36.33 (HCPh), 40.08 (HCCH2C=O), 47.53 (CH2), 51.45
(PhCCH2N), 126.47, 127.12, 127.45, 128.92, 129.60, 136.23,
139.81, 143.50 (Ar), 168.60 (HNCH2C=O), 174.33 (C=O,
lactam).
4-Chloro-N-[2-oxo-2-(2-oxo-4-phenylpyrrolidin-1-yl)ethyl]-
benzenesulfonamide (1b). Compound 3 (2.33 g, 0.01 mol) was
added dropwise to a suspension of compound 5b (2.68 g, 0.01 mol)
in anhydrous benzene (30 mL), and the mixture was refluxed for
1 h. After cooling, the reaction mixture was treated with EtOH
(20 mL). The formed crystals were filtered off. Compound 1b
with m.p. 147—148 °C was obtained in a yield of 2.10 g (53%).
Found (%): С, 55.19; Н, 4.55; N, 7.21. C18H17ClN2O4S.
Calculated (%): C, 55.03; H, 4.36; N, 7.13. IR, ν/cm–1: 3244.7
(N—H), 1749.6, 1684.7 (С=О), 1586.5, 1476.5 (Ar), 1162.8
(SO2), 749.1 (C—Cl). 1Н NMR (DMSO-d6), δ: 2.61—2.95
(m, 2 H, O=CCH2CHPh); 3.39—3.70 (m, 2 H, PhCHCH2N);
3.97—4.14 (m, 1 H, PhCH); 4.28 (d, 2 H, CH2, 3J = 8.02 Hz);
6.01—6.23 (m, 1 H, NH); 7.18—7.43 (m, 5 H, C6H5); 7.52
(d, 2 H, CHCClCH, 3J = 8.04 Hz); 7.82 (d, 2 H, CHС(SO2)CH,
3J = 8.01 Hz). 13C NMR (DMSO-d6), δ: 37.63 (HCPh), 41.35
(HCCH2C=O), 48.86 (CH2), 52.66 (PhCCH2N), 128.56, 130.08,
130.17, 130.67, 134.71, 139.81, 142.32 (Ar), 170.61 (HNCH2C=O),
176.25 (C=O, lactam).
4-Bromo-N-[2-oxo-2-(2-oxo-4-phenylpyrrolidin-1-yl)ethyl]-
benzenesulfonamide (1c). Compound 3 (2.33 g, 0.01 mol) was
added dropwise to a suspension of compound 5c (3.12 g, 0.01 mol)
and AlCl3 (0.05 g, 0.375 mmol) in toluene (30 mL). The mixture
was refluxed for 30 min. After cooling, the reaction mixture was
treated with EtOH (20 mL). The formed crystals were filtered
off. Compound 1c with m.p. 164—165 °C (MeCN) was obtained
in a yield of 1.39 g (32%). Found (%): С, 49.20; Н, 4.15; N, 6.35;
S, 7.15. C18H17BrN2O4S. Calculated (%): C, 49.44; H, 3.92;
N, 6.41; S, 7.33. IR, ν/cm–1: 3242,6 (N—H), 1749.6, 1684.8
(С=О), 1574.0, 1471.4 (Ar), 1170.0 (SO2), 550.7 (C—Br).
1Н NMR (CD3CN), δ: 2.35—2.74 (m, 2 H, O=CCH2CHPh);
3.16—3.47 (m, 2 H, PhCHCH2N); 3.75—3.91 (m, 1 H, PhCH);
4.04 (d, 2 H, CH2, 3J = 8.02 Hz); 5.88 (s, 1 H, NH); 6.96—7.20
(m, 5 H, Ph); 7.38—7.59 (m, 4 H, Ar). 13C NMR (CD3CN), δ:
37.47 (HCPh), 41.30 (HCCH2C=O), 48.72 (CH2), 52.64
(PhCCH2N), 127.8, 128.22, 128.42, 130.06, 131.89, 133.58,
141.37, 142.30 (Ar), 169.99 (HNCH2C=O), 176.11 (C=O,
lactam).
3J = 8.04 Hz); 8.28 (d, 2 H, CHСNO2CH, 3J = 8.01 Hz).
13C NMR (DMSO-d6), δ: 37.72 (HCPh), 41.41 (HCCH2C=O),
49.00 (CH2), 52.72 (PhCCH2N), 125.80, 128.34, 128.65, 129.80,
130.25, 142.38, 147.37 (Ar), 169.88 (HNCH2C=O), 176.42
(C=O, lactam). When benzene was used as a solvent, the yield
of sulfonamide 1d decreased to 20%.
4-Methyl-N-[2-oxo-2-(2-oxo-4-phenylpyrrolidin-1-yl)ethyl]-
benzenesulfonamide (2a). Compound 4 (1.57 g, 0.01 mol) was
added dropwise to a suspension of compound 5a (2.47 g, 0.01 mol)
in anhydrous benzene (30 mL), and the mixture was refluxed for
5 h. After cooling, the reaction mixture was treated with EtOH
(3 mL). The formed crystals were filtered off. Compound 2a with
m.p. 133—135 °C was obtained in a yield of 1.66 g (56%). Found
(%): С, 53.06; Н, 5.40; N, 9.15; S, 10.73. C13H16N2O4S.
Calculated (%): C, 52.69; H, 5.44; N, 9.45; S, 10.82. IR, ν/cm–1
:
3278.5 (N—H), 1733.4, 1687.1 (С=О), 1596.3, 1455.9 (Ar),
1
1159.6 (SO2). Н NMR (DMSO-d6), δ: 1.83—2.01 (m, 2 H,
СH2, lactam); 2.37 (s, 3 Н, CH3); 2.41—2.56 (m, 2 H, CH2C=O,
lactam); 3.57 (t, 2 H CH2NH, lactam, 3J = 6.96 Hz); 4.11 (d, 2 H,
CH2, 3J = 7.69 Hz); 7.38 (d, 2 H, CHС(СН3)СH, 3J = 7.69 Hz);
7.67 (d, 2 H, CHС(SO2)СH, 3J = 7.68 Hz); 7.91 (s, 1 H, NH).
13C NMR (DMSO-d6), δ: 17.04 (CH2, lactam), 20.97 (CH3),
32.70 (CH2, lactam), 45.00 (CH2NHSO2), 46.99 (CH2NC=O,
lactam), 126.53, 129.56, 137.75, 142.69 (Ar), 168.66
(HNCH2C=O), 176.09 (C=O lactam).
4-Chloro-N-[2-oxo-2-(2-oxopyrrolidin-1-yl)ethyl]benzene-
sulfonamide (2b). Compound 4 (1.38 g, 0.009 mol) was added
dropwise to a suspension of compound 5b (2.35 g, 0.009 mol) in
anhydrous benzene (30 mL). The mixture was refluxed for 2.5 h.
After cooling, the reaction mixture was treated with MeOH
(3 mL). The formed crystals were filtered off. Compound 2b with
m.p. 128—130 °C was obtained in a yield of 1.12 g (40%). Found (%):
С, 45.68; Н, 4.15; N, 8.23; S, 10.06. C12H13ClN2O4S. Calculat-
ed (%): C, 45.50; H, 4.14; N, 8.84; S, 10.12. IR, ν/cm–1: 3257.0
(N—H), 1750.5, 1690.6 (С=О), 1584.3, 1476.4 (Ar), 1158.0
(SO2), 763.5 (C—Cl). 1Н NMR (DMSO-d6), δ: 1.84—2.03 (m,
2 H, СH2, lactam); 2.39—2.63 (m, 2 H, CH2C=O, lactam);
3.44—3.67 (m, 2 H, CH2NH, lactam); 4.18 (d, 2 H, CH2,
3J = 8.01 Hz); 7.65 (d, 2 H, CHССlCH, 3J = 8.01 Hz); 7.80 (d,
2 H, CHС(SO2)CH, 3J = 8.06 Hz); 8.15 (s, 1 H, NH). 13C NMR
(DMSO-d6), δ: 17.04, 32.68 (СН2, lactam), 44.97 (CH2C=O,
lactam), 46.98 (CH2N, lactam), 128.45, 129.21, 137.25, 139.66
(Ar), 168.59 (HNCH2C=O), 176.11 (C=O, lactam).
4-Bromo-N-[2-oxo-2-(2-oxopyrrolidin-1-yl)ethyl]benzene-
sulfonamide (2c). Compound 4 (1.38 g, 0.009 mol) was added
dropwise to a suspension of compound 5c (3.13 g, 0.009 mol) in
anhydrous toluene (30 mL). The mixture was refluxed for 4 h.
After cooling, the reaction mixture was treated with EtOH (5 mL).
The formed crystals were filtered off. Compound 2c with m.p.
157—159 °C was obtained in a yield of 0.93 g (30%). Found (%):
С, 39.42; Н, 3.60; N, 7.24; S, 8.36. C12H13BrN2O4S. Calculat-
ed (%): C, 39.90; H, 3.63; N, 7.76; S, 8.88. IR, ν/cm–1: 3278.7
(N—H), 1751.2, 1671.7 (С=О), 1523.5 (Ar), 1167.8 (SO2), 608.0
4-Nitro-N-[2-oxo-2-(2-oxo-4-phenylpyrrolidin-1-yl)ethyl]-
benzenesulfonamide (1d). Compound 3 (1.16 g, 0.005 mol) was
added dropwise at room temperature to a suspension of compound
5d (1.39 g, 0.005 mol) in anhydrous acetonitrile (10 mL). The
reaction mixture was treated with EtOH (10 mL). The formed
crystals were filtered off. Compound 1d with m.p. 180—181 °C
(MeCN) was obtained in a yield of 0.94 g (47%). Found (%):
С, 53.37; Н, 4.25; N, 10.48; S, 7.64. C18H17N3O6S. Calculated (%):
C, 53.59; H, 4.25; N, 10.42; S, 7.95. IR, ν/cm–1: 3246.2 (N—H),
1750.2, 1686.3 (С=О), 1604.9, 1401.9 (Ar), 1527.1 (NO2),
1
(C—Br). Н NMR (DMSO-d6), δ: 1.87—1.99 (m, 2 H, СH2,
lactam); 2.39—2.63 (m, 2 H, CH2C=O, lactam); 3.57 (t, 2 H,
CH2NH, lactam, 3J = 6.96 Hz); 4.18 (d, 2 H, CH2, 3J = 5.50 Hz);
7.69—7.84 (m, 4 H, Ar); 8.15 (t, 1 H, NH, 3J = 5.50 Hz).
13C NMR (DMSO-d6), δ: 17.00 (CH2, lactam), 32.65
(HCCH2C=O), 44.93 (CH2), 46.93 (CH2N, lactam), 126.13,
128.51, 132.11, 140.05 (Ar), 168.55 (HNCH2C=O), 176.05
(C=O, lactam).
1
1163.9 (SO2). Н NMR (DMSO-d6), δ: 2.59—2.98 (m, 2 H,
O=CCH2CHPh); 3.39—3.70 (m, 2 H, OCCH2N); 3.95—4.19
(m, 1 H, CH); 4.33 (m, 2 H, PhCHCH2N); 6.16—6.55 (m, 1 H,
NH); 7.17—7.40 (m, 5 H, Ph); 8.04 (d, 2 H, CHC(SO2)CH,