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SHUKUR ET AL.
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(m, 3H); 7.88 (t, 1H, J = 7.6); 7.65 (t, 1H, J = 6.8); 7.37–7.24 (m, 5H), 7.02
(t, 1H, J = 7.2); 4.97 (s, 2H); 3.44 (s, 2H); 2.70–2.59 (m, 8H). 13C NMR
(DMSO‐d6) δ 165.81, 160.93, 153.41, 138.80, 136.25, 135.49, 130.73,
129.05, 128.08, 126.65, 125.18, 119.42, 112.51, 111.27, 103.68, 66.04,
62.72, 53.19, 43.71, 42.55. MS: 429.2 (MH+). Anal. calc. for
2‐(7,8,9,10‐Tetrahydro‐6‐oxo‐6H‐benzo[c]chromen‐3‐yloxy)‐N‐
benzyl‐N‐methylacetamide (THU‐4)
White powder, yield obtained 68%. IR: 1700 cm−1 (lactone carbonyl),
1676 cm−1 (amide carbonyl). 1H NMR (DMSO‐d6, 400 MHz):
7.48–7.18 (m, 6H); 6.85 (d, 1H, J = 9); 6.67 (d, 1H, J = 9); 4.81 (s, 2H);
4.60 (s, 2H); 2.99 (s, 3H); 2.74 (t, 2H, J = 5.8); 2.56 (t, 2H, J = 5.8);
1.86–1.78 (m, 4H). 13C NMR (DMSO‐d6) δ 167.36, 160.01, 153.30,
147.17, 136.46, 135.83, 129.08, 128.70, 127.67, 126.43, 121.01,
114.52, 112.26, 66.90, 52.78, 51.24, 34.22. MS: 378.1 (MH+). Anal.
calc. for C23H23NO4: C, 73.19; H, 6.14; N, 3.71. Found C, 72.80; H,
6.22; N, 3.56.
C26H24N2O4: C, 72.88; H, 5.65; N, 6.54. Found C, 73.41; H, 5.90;
N, 6.49.
2‐(6‐Oxo‐6H‐benzo[c]chromen‐3‐yloxy)‐N‐(naphthalen‐1‐yl)‐
acetamide (URO‐7)
Yellowish powder, yield obtained 60%. IR: 1718 cm−1 (lactone car-
bonyl), 1630 cm−1 (amide carbonyl). 1H NMR (DMSO‐d6, 400 MHz):
10.05 (s, 1H); 8.30–8.18 (m, 3H); 7.85–7.34 (m, 8H); 6.82–6.75 (m,
3H); 5.06 (s, 2H). 13C NMR (DMSO‐d6) δ 167.09, 161.88, 155.25,
145.78, 137.28, 134.07, 133.39, 131.48, 127.89, 126.19, 125.61,
124.26, 123.82, 117.51, 106.79, 102.60, 67.81. MS: 396.10 (MH+).
Anal. calc. for C25H17NO4: C, 75.94; H, 4.33; N, 3.54. Found C, 76.12;
H, 4.36; N, 3.47.
3‐(2‐Morpholino‐2‐oxoethoxy)‐7,8,9,10‐tetrahydrobenzo[c]chrom‐
en‐6‐one (THU‐5)
White powder, yield obtained 71%. IR: 1694 cm−1 (lactone carbonyl),
1651 cm−1 (amide carbonyl). 1H NMR (DMSO‐d6, 400 MHz): 7.48 (d,
1H, J = 8.8); 6.92 (d, 1H, J = 8.8); 6.82 (d, 1H, J = 2.8); 4.76 (s, 2H);
3.70–3.56 (m, 4H); 2.74 (t, 2H, J = 9.6); 2.56 (t, 2H, J = 8.0); 1.87–1.78
(m, 4H). 13C NMR (DMSO‐d6) δ 165.66, 159.36, 153.32, 147.06,
124.44, 121.23, 114.70, 111.88, 101.79, 67.33, 66.63, 45.73, 42.40,
29.69, 25.22. MS: 344.1 (MH+). Anal. calc. for C19H21NO5: C, 66.46;
H, 6.16; N, 4.08. Found C, 66.74; H, 6.14; N, 4.01.
2‐(6‐Oxo‐6H‐benzo[c]chromen‐3‐yloxy)‐N‐methyl‐N‐(prop‐2‐ynyl)‐
acetamide (URO‐8)
Brown powder, yield obtained 51%. IR: 1719 cm−1 (lactone carbonyl),
1668 cm−1 (amide carbonyl). 1H NMR (DMSO‐d6, 400 MHz):
8.33–8.18 (m, 3H); 7.89 (t, 1H, J = 7.2); 7.59 (t, 1H, J = 7.2); 7.00–6.91
(m, 2H); 5.00 (s, 2H); 3.02 (s, 2H); 2.89 (s, 3H); 2.08 (s, 1H). 13C NMR
3‐[2‐(4‐Benzylpiperazin‐1‐yl)‐2‐oxoethoxy]‐7,8,9,10‐
tetrahydrobenzo[c]chromen‐6‐one (THU‐6)
(DMSO‐d6)
δ
166.69, 160.06, 151.91, 135.40, 134.77, 129.73,
White powder, yield obtained 63%. IR: 1700 cm−1 (lactone carbonyl),
1654 cm−1 (amide carbonyl). 1H NMR (DMSO‐d6, 400 MHz): 7.43 (d, 1H,
J = 8.8); 7.30–7.25 (m, 5H); 6.89 (d, 1H, J = 9.0); 6.77 (d, 1H, J = 2.4); 4.75
(s, 2H); 3.51 (s, 2H); 2.71 (t, 2H, J = 9.6); 2.52 (t, 2H, J = 8.0); 2.44–2.40 (m,
4H); 1.83–1.77 (m, 4H). 13C NMR (DMSO‐d6) δ 165.37, 159.57, 153.20,
147.15, 137.39, 129.01, 128.32, 127.29, 124.32, 120.87, 114.42, 111.97,
101.72, 67.12, 62.72, 52.54, 45.09, 42.06, 29.26, 25.15, 23.82. MS: 432.2
(M+). Anal. calc. for C26H28N2O4: C, 72.20; H, 6.53; N, 6.48. Found C,
71.88; H, 6.39; N, 6.57.
128.22, 124.64, 122.05, 112.91, 102.33, 74.38, 65.67, 40.11, 35.82.
MS: 322.0 (MH+). Anal. calc. for C19H15NO4: C, 71.02; H, 4.71; N,
4.36. Found C, 71.28; H, 4.70; N, 4.33.
2‐(6‐Oxo‐6H‐benzo[c]chromen‐3‐yloxy)‐Nʹ‐phenylacetohydrazide
(URO‐9)
Yellow powder, yield obtained 48%. IR: 1719 cm−1 (lactone carbonyl),
1641 cm−1 (amide carbonyl). 1H NMR (DMSO‐d6, 400 MHz): 11.01 (s,
1H); 10.05 (s, 1H); 8.30–8.22 (m, 3H); 7.89 (t, 1H, J = 7.2); 7.59 (t, 1H,
J = 7.2); 7.11–6.91 (m, 7H); 5.07 (s, 2H). 13C NMR (DMSO‐d6): δ
168.80, 160.54, 154.27, 137.93, 135.49, 134.85, 129.27, 128.64,
125.73, 123.86, 122.48, 119.82, 112.81, 111.48, 102.66, 67.49. MS:
361.0 (MH+). Anal. calc. for C21H16N2O4: C, 69.99; H, 4.48; N, 7.77.
Found C, 70.48; H, 4.74; N, 7.60.
2‐(7,8,9,10‐Tetrahydro‐6‐oxo‐6H‐benzo[c]chromen‐3‐yloxy)‐N‐
(naphthalen‐1‐yl)acetamide (THU‐7)
Light yellow powder, yield obtained 58%. IR: 1705 cm−1 (lactone
carbonyl), 1662 cm−1 (amide carbonyl). 1H NMR (DMSO‐d6,
400 MHz): 10.33 (s, 1H); 7.50–7.14 (m, 8H); 6.95 (d, 1H, J = 9.0); 6.73
(d, 1H, J = 2.8); 5.01 (s, 2H); 2.73 (t, 2H, J = 5.6); 2.44 (t, 2H, J = 5.6);
1.71–1.66 (m, 4H). 13C NMR (DMSO‐d6) δ 167.01, 160.39, 154.41,
147.26, 145.28, 134.83, 132.91, 128.52, 127.26, 126.45, 124.06,
123.62, 120.07, 116.55, 114.93, 112.84, 108.41, 103.86, 68.35,
26.21, 25.09, 22.27. MS: 400.2 (MH+). Anal. calc. for C25H21NO4: C,
75.17; H, 5.30; N, 3.51. Found C, 75.41; H, 5.20; N, 3.39.
3‐[2‐(3,4‐Dihydro‐6,7‐dimethoxyisoquinolin‐2(1H)‐yl)‐2‐oxoethoxy]‐
6H‐benzo[c]chromen‐6‐one (URO‐10)
Brown‐yellow powder, yield obtained 58%. IR: 1724 cm−1 (lac-
tone carbonyl), 1665 cm−1 (amide carbonyl). 1H NMR (DMSO‐d6,
400 MHz): 8.31–8.17 (m, 3H); 7.89 (t, 1H, J = 7.2); 7.58 (t, 1H,
J = 7.6); 7.03–6.99 (m, 2H); 6.80–6.72 (m, 2H); 5.04 (s, 2H);
3.72–3.63 (m, 10H); 3.27–3.17 (m, 2H). 13C NMR (DMSO‐d6) δ
166.22, 160.47, 151.90, 147.46, 135.36, 134.68, 129.69, 128.16,
126.01, 124.70, 122.01, 119.27, 112.82, 102.33, 66.24, 55.51,
44.85. MS: 446.01 (MH+). Anal. calc. for C26H23NO6: C, 70.10; H,
5.20; N, 3.14. Found C, 70.14; H, 5.12; N, 3.21.
2‐(7,8,9,10‐Tetrahydro‐6‐oxo‐6H‐benzo[c]chromen‐3‐yloxy)‐N‐
methyl‐N‐(prop‐2‐ynyl)acetamide (THU‐8)
White powder, yield obtained 58%. IR: 1695 cm−1 (lactone carbonyl),
1670 cm−1 (amide carbonyl). 1H NMR (DMSO‐d6, 400 MHz): 7.47 (d,
1H, J = 8.8); 6.92 (d, 1H, J = 9.0); 6.78 (d, 1H, J = 2.4); 4.76 (s, 2H);