Paper
NJC
(t, J = 5.1 Hz, 2H), 4.01 (s, 2H), 3.77 (t, J = 5.1 Hz, 2H), 2.38 (s, 1H), 4.11 (t, J = 5.0 Hz, 2H), 3.96 (s, 2H), 3.74 (t, J = 4.9 Hz, 2H),
3H); 13C NMR (101 MHz, CDCl3) d: 192.2, 183.8, 173.4, 150.7, 2.36 (s, 3H), 2.08 (s, 3H); 13C NMR (101 MHz, CDCl3) d: 191.9,
129.3, 129.1, 125.6, 102.4, 71.5, 57.7, 41.8, 19.5; HRMS (ESI): m/ 183.9, 173.3, 156.3, 130.9, 126.9, 126.4, 121.0, 110.5, 102.4, 66.3,
z calcd for C14H14Cl2NO4 ([M + H]+) 330.0294, found 330.0292. 57.6, 41.4, 19.5, 16.5; HRMS (ESI): m/z calcd for C15H18NO4
(Z)-3-(1-Hydroxyethylidene)-1-(2-(2,4,5-trichlorophenoxy)ethyl) ([M + H]+) 276.1230, found 276.1215.
pyrrolidine-2,4-dione (10g). Light red powder, yield: 52%, m.p.
(Z)-3-(1-Hydroxyethylidene)-1-(2-(m-tolyloxy)ethyl)pyrrolidine-
152.2–155.3 1C; IR (KBr) (nmax/cmꢀ1): 3094, 2947, 2921, 2879, 2,4-dione (10m). Light red powder, yield: 49%, m.p. 47.8–50.4 1C;
1702, 1614, 1450, 1237, 1077, 892, 719; 1H NMR (400 MHz, IR (KBr) (nmax/cmꢀ1): 3050, 2973, 2924, 2884, 1714, 1644, 1474,
DMSO-d6) d: 7.84 (s, 1H), 7.54 (s, 1H), 4.33 (t, J = 5.0 Hz, 2H), 1246, 1054, 939, 767; 1H NMR (400 MHz, DMSO-d6) d: 7.16 (t, J =
4.04 (s, 2H), 3.80 (t, J = 5.0 Hz, 2H), 2.41 (s, 3H); 13C NMR 7.8 Hz, 1H), 6.77–6.73 (m, 3H), 4.13 (t, J = 5.3 Hz, 2H), 3.97
(101 MHz, CDCl3) d: 191.9, 183.9, 173.3, 152.8, 131.4, 131.1, (s, 2H), 3.73 (t, J = 5.3 Hz, 2H), 2.38 (s, 3H), 2.26 (s, 3H); 13C NMR
124.9, 121.9, 114.4, 102.4, 68.3, 57.9, 41.0, 19.5; HRMS (ESI): (101 MHz, CDCl3) d: 192.0, 183.8, 173.3, 158.1, 139.8, 129.4,
m/z calcd for C14H13Cl3NO4 ([M + H]+) 363.9905, found 363.9893. 122.2, 115.3, 111.1, 102.4, 66.5, 57.6, 41.2, 21.5, 19.5; HRMS (ESI):
(Z)-3-(1-Hydroxyethylidene)-1-(2-(2,4,6-trichlorophenoxy)ethyl) m/z calcd for C15H18NO4 ([M + H]+) 276.1230, found 276.1232.
pyrrolidine-2,4-dione (10h). White powder, yield: 54%, m.p. 94.0–
(Z)-3-(1-Hydroxyethylidene)-1-(2-(p-tolyloxy)ethyl)pyrrolidine-
97.0 1C; IR (KBr) (nmax/cmꢀ1): 3080, 2940, 2889, 1716, 1634, 1439, 2,4-dione (10n). White powder, yield: 52%, m.p. 77.7–78.5 1C; IR
1
1239, 1035, 987, 866, 722; H NMR (400 MHz, DMSO-d6) d: 7.73 (KBr) (nmax/cmꢀ1): 3029, 2972, 2929, 2882, 1705, 1648, 1475,
(s, 2H), 4.15 (t, J = 5.1 Hz, 2H), 4.02 (s, 2H), 3.79 (t, J = 5.1 Hz, 2H), 1046, 807, 719; 1H NMR (400 MHz, DMSO-d6) d: 7.08 (d, J = 8.3
2.41 (s, 3H); 13C NMR (101 MHz, CDCl3) d: 192.0, 183.9, 173.4, Hz, 2H), 6.84 (d, J = 8.4 Hz, 2H), 4.11 (t, J = 5.4 Hz, 2H), 3.96
149.7, 130.2, 129.9, 128.9, 102.4, 71.7, 57.6, 41.7, 19.5; HRMS (s, 2H), 3.72 (t, J = 5.4 Hz, 2H), 2.38 (s, 3H), 2.22 (s, 3H); 13C NMR
(ESI): m/z calcd for C14H13Cl3NO4 ([M + H]+) 363.9905, found (101 MHz, CDCl3) d: 192.1, 183.8, 173.3, 155.9, 130.7, 130.1,
363.9893.
114.2, 102.4, 66.7, 57.6, 41.2, 20.5, 19.5; HRMS (ESI): m/z calcd
(Z)-1-(2-(4-Chloro-2-methylphenoxy)ethyl)-3-(1-hydroxyethylidene) for C15H18NO4 ([M + H]+) 276.1230, found 276.1231.
pyrrolidine-2,4-dione (10i). Light red powder, yield: 49%, m.p. 86.4–
(Z)-1-(2-(3,5-Dimethylphenoxy)ethyl)-3-(1-hydroxyethylidene)
90.7 1C; IR (KBr) (nmax/cmꢀ1): 3113, 3034, 2946, 2923, 2873, 1706, pyrrolidine-2,4-dione (10o). White powder, yield: 60%, m.p.
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1613, 1481, 1241, 1044, 992, 862, 805, 722; H NMR (400 MHz, 80.3–82.4 1C; IR (KBr) (nmax/cmꢀ1): 3014, 2962, 2918, 2875,
DMSO-d6) d: 7.19 (dd, J = 7.8, 5.4 Hz, 2H), 6.94 (d, J = 8.5 Hz, 1H), 1712, 1621, 1472, 1067, 835, 721; 1H NMR (400 MHz, DMSO-
4.14 (t, J = 5.2 Hz, 2H), 3.97 (s, 2H), 3.76 (t, J = 5.2 Hz, 2H), 2.38 d6) d: 6.54 (d, J = 4.8 Hz, 3H), 4.07 (t, J = 5.3 Hz, 2H), 3.93 (s, 2H),
(s, 3H), 2.10 (s, 3H); 13C NMR (101 MHz, CDCl3) d: 191.8, 184.0, 3.69 (t, J = 5.3 Hz, 2H), 2.35 (s, 3H), 2.18 (s, 6H); 13C NMR (101
173.4, 154.9, 130.7, 128.3, 126.5, 125.7, 111.6, 102.3, 66.6, 57.4, 41.3, MHz, CDCl3) d: 192.1, 183.8, 173.3, 158.1, 139.5, 123.1, 112.1,
19.5, 16.3; HRMS (ESI): m/z calcd for C15H17ClNO4 ([M + H]+) 102.4, 66.4, 57.6, 41.3, 21.4, 19.5; HRMS (ESI): m/z calcd for
310.0841, found 310.0841.
C
16H20NO4 ([M + H]+) 290.1387, found 290.1391.
(Z)-3-(1-Hydroxyethylidene)-1-(2-phenoxyethyl)pyrrolidine-
(Z)-3-(1-Hydroxyethylidene)-1-(2-(2-methoxyphenoxy)ethyl)
2,4-dione (10j). Light red powder, yield: 57%, m.p. 65.3–66.5 1C; pyrrolidine-2,4-dione (10p). White powder, yield: 54%, m.p.
IR (KBr) (nmax/cmꢀ1): 3054, 2946, 2925, 2878, 1717, 1614, 1480, 80.0–82.0 1C; IR (KBr) (nmax/cmꢀ1): 3066, 3016, 2964, 2882,
1232, 1086, 894, 752; 1H NMR (400 MHz, DMSO-d6) d: 7.28 (t, J = 2834, 1714, 1654, 1507, 1483, 1224, 1022, 737; 1H NMR
7.9 Hz, 2H), 6.94 (t, J = 7.3 Hz, 3H), 4.15 (t, J = 5.3 Hz, 2H), 3.97 (400 MHz, DMSO-d6) d: 6.97–6.84 (m, 4H), 4.09 (t, J = 5.4 Hz,
(s, 2H), 3.74 (t, J = 5.3 Hz, 2H), 2.38 (s, 3H); 13C NMR (101 MHz, 2H), 4.00 (s, 2H), 3.72–3.69 (m, 5H), 2.36 (s, 3H); 13C NMR
CDCl3) d: 192.0, 183.8, 173.3, 158.0, 129.7, 121.4, 114.3, 102.4, (101 MHz, CDCl3) d: 192.4, 183.6, 173.2, 149.6, 147.6, 122.1,
66.5, 57.6, 41.2, 19.5; HRMS (ESI): m/z calcd for C14H16NO4 120.8, 113.8, 111.8, 102.5, 68.0, 57.9, 55.7, 41.3, 19.5; HRMS
([M + H]+) 262.1074, found 262.1074.
(ESI): m/z calcd for C15H18NO5 ([M + H]+) 292.1179, found
(Z)-3-(1-Hydroxyethylidene)-5-methyl-1-(2-phenoxyethyl) 292.1182.
pyrrolidine-2,4-dione (10k). Yellow oil, yield: 55%; IR (KBr)
(Z)-3-(1-Hydroxyethylidene)-1-(2-(2-methoxyphenoxy)ethyl)-
(nmax/cmꢀ1): 3061, 3042, 2980, 2937, 2877, 1713, 1628, 1597, 5-methylpyrrolidine-2,4-dione (10q). White powder, yield: 52%,
1461, 1229, 1051, 914, 757; 1H NMR (400 MHz, DMSO-d6) d: m.p. 76.0–77.0 1C; IR (KBr) (nmax/cmꢀ1): 3066, 3025, 2937, 2873,
7.26 (t, J = 8.0 Hz, 2H), 6.91 (dd, J = 7.3, 4.7 Hz, 3H), 4.13–4.11 2834, 1709, 1626, 1505, 1461, 1214, 1017, 738; 1H NMR (400
(m, 2H), 4.02–3.94 (m, 2H), 3.52–3.45 (m, 1H), 2.36 (s, 3H), 1.27 MHz, DMSO-d6) d: 6.99–6.96 (m, 2H), 6.93–6.85 (m, 2H), 4.19–
(d, J = 7.0 Hz, 3H); 13C NMR (101 MHz, CDCl3) d: 195.3, 184.2, 3.99 (m, 4H), 3.72 (s, 3H), 3.54–3.45 (q, J = 4.0 Hz, 1H), 2.39
172.8, 158.1, 129.6, 121.3, 114.3, 101.2, 66.3, 62.5, 39.0, 19.5, (s, 3H), 1.31 (d, J = 6.9 Hz, 3H); 13C NMR (101 MHz, CDCl3) d:
15.2; HRMS (ESI): m/z calcd for C15H18NO4 ([M + H]+) 276.1230, 195.7, 184.0, 172.7, 149.6, 147.7, 122.0, 120.8, 113.7, 111.8,
found 276.1240.
101.3, 67.7, 62.7, 55.7, 38.9, 19.5, 15.0; HRMS (ESI): m/z calcd
(Z)-3-(1-Hydroxyethylidene)-1-(2-(o-tolyloxy)ethyl)pyrrolidine- for C16H20NO5 ([M + H]+) 306.1336, found 306.1332.
2,4-dione (10l). Light red powder, yield: 48%, m.p. 96.6–96.7 1C;
(Z)-3-(1-Hydroxyethylidene)-1-(2-(3-methoxyphenoxy)ethyl)
IR (KBr) (nmax/cmꢀ1): 3062, 3033, 2947, 2915, 2878, 1709, 1613, pyrrolidine-2,4-dione (10r). White powder, yield: 62%, m.p.
1481, 1236, 1016, 753, 721; 1H NMR (400 MHz, DMSO-d6) d: 65.5–68.0 1C; IR (KBr) (nmax/cmꢀ1): 3069, 3007, 2950, 2923,
7.11 (t, J = 7.9 Hz, 2H), 6.89 (d, J = 7.9 Hz, 1H), 6.81 (t, J = 7.3 Hz, 2885, 2837, 1711, 1615, 1587, 1473, 1200, 1046, 847, 759;
This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021
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| New J. Chem., 2021, 45, 5621–5630