KEIVANLOO ET AL.
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1,200, 1,120, 870, 767 cm−1; H-NMR (300 MHz, CDCl3):
δ 4.62 (s, 2H, CH2), 7.39–7.48 (m, 11H, PhH, and ArH),
7.52 (d, J = 8.1 Hz, 1H, ArH), 7.71 (d, J = 7.8 Hz, 1H,
ArH), 8.18–8.22 (m, 1H, ArH), 8.26 (s, 1H, NH) ppm; 13C-
NMR (75 MHz, CDCl3): δ 28.9, 70.5, 81.0, 85.0, 123.4,
124.0, 126.8, 126.9, 128.8, 128.9, 129.3, 137.6, 138.8, 148.0,
155.5, 172.3 ppm; m/z [M]+ 411. Anal. calcd. for
C24H17N3O4: C, 70.07; H, 4.17; N, 10.21; found: C,
70.12; H, 4.19; N, 10.25%.
9.77 (s, 1H, NH) ppm; 13C-NMR (75 MHz, DMSO-d6): δ
34.2, 58.8, 69.8, 82.7, 85.9, 125.2, 127.2, 128.7, 129.0,
136.1, 140.0, 148.5, 155.3, 157.6, 173.3 ppm; m/z [M]+
396. Anal. calcd. for C25H20N2O3: C, 75.74; H, 5.09; N,
7.07; found: C, 75.82; H, 5.10; N, 7.03%.
3.3.5 | 5,5-Diphenyl-3-(3-(p-tolyl)prop-
2-yn-1-yl)imidazolidine-2,4-dione (5e)
Yellow powder solid (80% yield): mp, 106–107ꢀC; IR
(KBr): 3,312 (NH), 3,082, 2,995, 1,769 (C O), 1,712
(C O), 1,600, 1,550, 1,488, 1,446, 1,331, 1,254, 1,209,
3.3.2 | 5,5-Diphenyl-3-(3-phenylprop-
2-yn-1-yl)imidazolidine-2,4-dione (5b)
1
1,120, 1,046, 940 cm−1; H-NMR (300 MHz, DMSO-d6): δ
Yellow powder solid (87% yield): mp, 102–103ꢀC; IR
(KBr): 3,310 (NH), 3,070, 2,925, 2,847, 1,771 (C O), 1,715
(C O), 1,559, 1,532, 1,490, 1,443, 1,350, 1,252, 1,209,
2.30 (s, 3H, CH3), 4.31 (s, 2H, CH2), 7.37–7.55 (m, 14H,
PhH, and ArH), 9.79 (s, 1H, NH) ppm; 13C-NMR (75 MHz,
DMSO-d6): δ 22.8, 33.7, 69.8, 82.8, 86.1, 128.9, 131.2, 132.1,
134.8, 135.0, 137.5, 144.3, 149.0, 156.7, 173.6 ppm; m/z
[M]+ 380. Anal. calcd. for C25H20N2O2: C, 78.93; H,
5.30; N, 7.36; found: C, 78.90; H, 5.33; N, 7.40%.
1
1,174, 940, 707 cm−1; H-NMR (300 MHz, DMSO-d6): δ
4.54 (s, 2H, CH2), 7.36–7.47 (m, 15H, ArH, and ArH),
9.85 (s, 1H, NH) ppm; 13C-NMR (75 MHz, DMSO-d6): δ
28.9, 69.8, 82.6, 84.3, 122.0, 127.1, 128.8, 129.1, 129.2,
129.4, 131.9, 139.8, 154.7, 172.9 ppm; m/z [M]+ 366. Anal.
calcd. for C24H18N2O2: C, 78.67; H, 4.95; N, 7.65;
found: C, 78.64; H, 4.97; N, 7.60%.
3.3.6 | 3-(3-(4-Chloro-3-nitrophenyl)prop-
2-yn-1-yl)-5,5-diphenylimidazolidine-
2,4-dione (5f)
3.3.3 | 3-(3-(4-Nitrophenyl)prop-2-yn-
1-yl)-5,5-diphenylimidazolidine-
2,4-dione (5c)
White powder solid (83% yield): mp, 115–118ꢀC; IR
(KBr): 3,300 (NH), 3,075, 2,928, 1,772 (C O), 1,712
(C O), 1,589, 1,580, 1,500 (NO2), 1,461, 1,345 (NO2),
12,365, 1,208, 1,139, 1,112, 873, 779 cm−1 1H-NMR
;
Yellow powder solid (96% yield): mp, 110–111ꢀC; IR
(KBr): 3,300 (NH), 3,050, 2,987, 1,769 (C O), 1,718
(C O), 1,597, 1,520 (NO2), 1,433, 1,345 (NO2), 1,107,
(300 MHz, DMSO-d6): δ 4.84 (s, 2H, CH2), 7.35–7.45 (m,
10H, PhH), 8.03 (d, J = 8.7 Hz, 1H, ArH), 8.30 (dd,
J = 8.8, 2.5 Hz, 1H, ArH), 8.72 (d, J = 2.4 Hz, 1H, ArH),
9.75 (s, 1H, NH) ppm; 13C-NMR (75 MHz, DMSO-d6): δ
33.8, 69.9, 84.1, 87.5, 122.5, 125.0, 125.2, 127.2, 128.7,
129.0, 136.9, 139.4, 144.0, 148.5, 155.9, 173.3 ppm; m/z
[M]+ 445. Anal. calcd. for C24H16ClN3O4: C, 64.65; H,
3.62; N, 9.42; found: C, 64.69; H, 3.60; N, 9.45%.
1
1,043, 985, 851, 774 cm−1; H-NMR (300 MHz, DMSO-
d6): δ 4.31 (s, 2H, CH2), 7.37–7.47 (m, 10H, ArH), 7.65 (d,
J = 9 Hz, 2H, ArH), 8.18 (d, J = 8.7 Hz, 2H, ArH), 9.79 (s,
1H, NH) ppm; 13C-NMR (75 MHz, DMSO-d6): δ 28.6,
71.4, 83.5, 86.1, 128.8, 131.2, 131.4, 134.8, 135.0, 141.2,
144.5, 147.3, 156.7, 173.1 ppm; m/z [M]+ 411. Anal. calcd.
for C24H17N3O4: C, 70.07; H, 4.17; N, 10.21; found: C,
70.01; H, 4.13; N, 10.20%.
3.3.7 | 3-(3-(2-Chloro-4-nitrophenyl)prop-
2-yn-1-yl)-5,5-diphenylimidazolidine-
2,4-dione (5g)
3.3.4 | 3-(3-(4-Methoxyphenyl)prop-2-yn-
1-yl)-5,5-diphenylimidazolidine-
2,4-dione (5d)
Yellow powder solid (81% yield): mp, 120–122ꢀC; IR
(KBr): 3,298 (NH), 3,065, 2,980, 1,775 (C O), 1,712
(C O), 1,590, 1,530 (NO2), 1,491, 1,447, 1,350, 1,235,
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White powder solid (82% yield): mp, 98–100ꢀC; IR (KBr):
3,335 (NH), 3,020, 2,965, 1,764 (C O), 1,720 (C O),
1,598, 1,530, 1,458, 1,348, 1,230, 1,100, 1,051, 980, 840,
1,134, 1,048, 820, 776 cm−1; H-NMR (300 MHz, DMSO-
d6): δ 4.88 (s, 2H, CH2), 7.37–7.43 (m, 10H, PH), 8.03 (d,
J = 9 Hz, 1H, ArH), 8.41 (dd, J = 8.7, 2.4 Hz, 1H, ArH),
8.63 (d, J = 1.8 Hz, 1H, ArH), 9.72 (s, 1H, NH) ppm; 13C-
NMR (75 MHz, DMSO-d6): δ 33.7, 69.6, 84.8, 88.2, 124.1,
126.3, 126.8, 127.8, 129.7, 129.8, 131.3, 139.5, 143.3, 148.8,
1
765 cm−1; H-NMR (300 MHz, DMSO-d6): δ 3.90 (s, 3H,
OCH3), 4.54 (s, 2H, CH2), 7.19 (d, J = 8.7 Hz, 2H, ArH),
7.35–7.38 (m, 10H, PhH), 7.99 (d, J = 9 Hz, 2H, ArH),