K. M. Khan et al. / Bioorg. Med. Chem. 17 (2009) 2983–2988
2987
2972 (Ar CH), 3074 (ArCH) cmꢀ1
;
1H NMR (500 MHz, CD3OD) d:
(96.35), 91.9 (100); Anal. Calcd for C17H11NO4: (293) [Found: C,
69.73; H, 3.80; N, 4.75. Requires: C, 69.62; H, 3.78; N, 4.78].
8.30 (s, 1H H-2), 7.98 (dd, J5,7 = 1.0 Hz, J5,6 = 7.6 Hz, 1H, H-5), 7.55
(td, J7,5 = 1.5, J7,6 = J7,8 = 7.8 Hz, 1H, H-7), 7.29 (d, J 8,7 = 7.8 Hz, 1H,
H-8), 7.11 (t, J6,8 = 3.1, J6,7 = J6,5 = 7.8 Hz, 1H, H-6), 5.80 (s, 1H,
CH@N), 1.54 (s, 9H, 3CH3); EI MS: m/z (rel. abund.%) 229 (M+,
16), 200 (47), 172 (75), 121 (96); Anal. Calcd for C14H15NO2:
(229) [Found: C, 73.32; H, 6.58; N, 6.12. Requires: C, 73.34; H,
6.59; N, 6.11].
4.14. 3-{[(1-Benzyl-2-hydroxyethyl)imino]methyl}-4H-
chromen-4-one (16)
Yield = 63%; mp = 110 °C; Rf = 0.52 (EtOAc/Hex, 3:7); UV
(MeOH); kmax 206.8 (log
e
= 4.12) nm; IR (KBr): mmax 3066 (ArCH),
2920 (CH), 1645.3 (C@O) cmꢀ1
,
1H NMR (400 MHz, CDCl3) d: 8.01
4.10. 3-{[(3-Methoxy-4-methylphenyl) imino] methyl}-4H-
(s, 1H, H-2), 7.50–8.24 (m, 4H, ArH), 7.02–7.40 (m, 4H, H-5,6,7,8),
chromen-4-one (12)
6.56 (s, 1H, CH@N), 3.57–3.85 (m, 1H, CH2CHCH2–OH), 3.07 (d,
0
0
J1 ,2 = 5.5 Hz, 2H, CH2CHCH2–OH), 2.91 (m, 2H, CH2–CHCH2OH), EI
MS: m/z (rel. abund.%) 307 (M+, 5.16), 276 (16.85), 215.9 (41.09),
172 (23.12), 159 (50.14), 145.9 (14.37), 120 (59.07), 105 (16.32);
Anal. Calcd for C19H17NO3: (307) [Found: C, 75.49; H, 5.57; N,
5.65. Requires: C, 74.25; H, 5.58; N, 4.56].
Yield = 72%; mp = 86 °C; Rf = 0.42 (EtOAc/Hex, 3:7); UV (MeOH);
kmax 307.6 (log
(ArCH) cmꢀ1 1H NMR (300 MHz, CD3OD) d: 8.50 (s, 1H, H-2),
7.42–7.90 (m, 4H, H-5,6,7,8), 7.03 (d, J5 ,6 = 7.5 Hz, 1H, H-50), 6.93
e = 4.5) nm; IR (KBr): mmax 1648.5 (C@O), 909.7
;
0
0
(s, 1H, H-20), 6.72 (d, J6 ,5 = 7.5 Hz, 1H, H-60), 6.14 (s, 1H, CH@N),
3.7 (s, 3H, OCH3), 1.27 (s, 3H, CH3); EI MS: m/z (rel. abund.%) 292
(M+, 100), 276 (41.09), 188 (18.29), 172 (57.53), 145.8 (55.69),
120.8 (54.16), 90.9 (11.32); Anal. Calcd for C18H15NO3: (293)
[Found: C, 73.70; H, 5.16; N, 4.80. Requires: C, 73.71; H, 5.15; N,
4.78].
0
0
4.15. 3-{[(3-Hydroxy-2-pyridinyl)imino]methyl}-4H-chromen-
4-one (17)
Yield = 62%; mp = 144 °C; Rf = 0.5 (EtOAc/Hex, 3:7); UV (MeOH);
kmax 209.4 (log
e
= 4.3) nm; IR (KBr):
mmax 1645.3 (C@O), 1291.1 (C–
N), 3066 (ArCH) cmꢀ1
;
1H NMR (300 MHz, DMSO-d6) d: 10.30 (s,
0
0
4.11. 3-{[(3-Methoxyphenyl)imino]methyl}-4H-chromen-4-one
(13)
1H, OH), 8.63 (d, J6 ,5 = 7.2 Hz, 1H, H-60), 8.30 (s, 1H, H-2), 7.49 (t,
J7,8 = J7,6 = 8.1 Hz, 1H, H-7), 7.37 (d, J4 ,5 = 7.2 Hz, 1H, H-40), 7.22
(d, J5,6 = 7.5 Hz, 1H, H-5), 7.09 (t, J6,5 = J6,7 = 7.5 Hz, 1H, H-6), 7.04
0
0
0
0
0
0
Yield = 43%; mp = 178 °C; Rf = 0.35 (EtOAc/Hex, 5:5); UV
(d, J8,7 = 8.1 Hz, 1H, H-8), 6.95 (t, J5 ,6 = J5 ,4 = 7.2 Hz, 1H, H-50),
6.93 (s, 1H, CH@N); EI MS: m/z (rel. abund.%) 265 (M+, 28), 262
(7), 248 (3), 237 (24), 210 (7), 172 (48), 146 (4), 120 (30), 95
(88), 77 (16); Anal. Calcd for C15H10N2O3: (265) [Found: C, 67.69;
H, 4.0; N, 10.30. Requires: C, 67.67; H, 3.79; N, 10.52].
(MeOH); kmax 204 (log
e
= 4.5) nm; IR (KBr): mmax 1205.3 (O-CH3
;
stretch), 908.9 (ArCH) cmꢀ1
1H NMR (300 MHz, CDCl3) d: 8.82 (s,
1H, H-2), 7.97 (dd J5,7 = 1.5 Hz, J5,6 = 8.8 Hz, 1H, H-5), 7.52 (t,
J7,6 = J7,8 = 7.5 Hz, 1H, H-7), 7.28 (d, J6 ,5 = 7.2 Hz, 1H, H-60), 7.09
(d, J8,7 = 8.3 Hz, 1H, H-8), 6.92 (t, J6,5 = J6,7 = 7.5 Hz, 1H, H-6), 6.78
0
0
(s, 1H, H-20), 6.75 (t, J5 ,4 = J5 ,6 = 8.3 Hz, 1H, H-50), 6.65–6.73 (m,
1H, H-40), 6.51 (s, 1H, CH@N), 4.01 (s, 3H, OCH3); EI MS: m/z (rel.
abund.%) 278 (M+, 52.6), 264 (4), 250 (43.85), 120 (77); Anal. Calcd
for C17H13NO3: (279) [Found: C, 73.14; H, 4.66; N, 5.03. Requires: C,
73.11; H, 4.69; N, 5.02].
4.16. 3-[(4-Pyridinylimino) methyl]-4H-chromen-4-one (18)
0
0
0
0
Yield = 60%; mp = 140 °C; Rf = 0.34 (EtOAc/Hex, 5:5); UV
(MeOH); kmax 201.9 (log
1284.4 (C–N) cmꢀ1
e = 4.4) nm; IR (KBr): mmax 1645.3 (C@O),
;
1H NMR (400 MHz, CDCl3) d: 8.68 (s, 1H,
CH@N), 8.52 (s, 1H, H-2), 8.17 (s, 1H, H-20), 7.91 (d, J4 ,5 = 7.2 Hz,
0
0
4.12. 3-{[(2-Methoxy-4-nitrophenyl) imino] methyl}-4H-
1H, H-40), 7.72 (t, J7,8 = J7,6 = 7.5 Hz, 1H, H-7), 7.58 (t,
0
0
0
0
0
0
chromen-4-one (14)
J5 ,4 = J5 ,6 = 7.2 Hz, 1H, H-50), 7.47 (d, J6 ,5 = 7.2 Hz, 1H, H-60), 7.22
(d, J5,6 = 7.5 Hz, 1H, H-5), 7.12 (t, J6,5 = J6,7 = 7.5 Hz, 1H, H-6), 7.02
(d, J8,7 = 8.4 Hz, 1H, H-8); EI MS: m/z (rel. abund.%) 249 (M+, 62),
172 (55), 146 (33), 120 (38); Anal. Calcd for C15H10N2O2: (249)
[Found: C, 71.93; H, 4.04; N, 11.18. Requires: C, 71.99; H, 4.03;
N, 11.19].
Yield = 63%; mp = 268 °C; Rf = 0.46 (EtOAc/Hex, 3:7); UV
(MeOH); kmax 217.2 (log
e
= 5.0) nm; IR (KBr): mmax 1655.5 (C@O),
1589.7 (C@N), 3100.2 (ArCH) cmꢀ1
;
1H NMR (400 MHz, CDCl3) d:
8.50 (s, 1H, H-2), 8.21 (d, J5,6 = 8.1 Hz, 1H, H-5), 7.72 (d,
J5 ,6 = 8.5 Hz, 1H, H-50), 7.70 (t, J7,6 = J7,8 = 7.5 Hz, 1H, H-7), 7.61 (s,
0
0
1H, H-30), 7.43 (d, J8,7 = 8.1 Hz, 1H, H-8), 7.42 (s, 1H, CH@N), 7.40
4.17. 3-[(3-Pyridinylimino) methyl]-4H-chromen-4-one (19)
(t, J6,5 = J6,7 = 8.1 Hz, 1H, H-6), 6.61 (d, J6 ,5 = 8.5 Hz, 1H, H-60),
3.90 (s, 3H, OCH3); EI MS: m/z (rel. abund.%) 323 (M+, 9.39), 308
(41.6), 262 (19.87), 234 (3.68), 172 (100), 120 (60.01), 91 (60);
Anal. Calcd for C17H12N2O5: (324) [Found: C, 62.98; H, 3.71; N,
8.62. Requires: C, 62.96; H, 3.73; N, 8.64].
0
0
Yield = 62%; mp = 140 °C; Rf = 0.35 (EtOAc/Hex, 5:5); UV
(MeOH); kmax 201.4 (log
e
;
= 4.3) nm; IR (KBr): mmax 1645.3 (C@O),
1H NMR (400 MHz, CDCl3) d: 8.68 (s,
1291.1 (C-N), 3066 cmꢀ1
1H, H-10), 8.50 (s, 1H, H-2), 7.98 (d, J3 ,2 = J5 ,6 = 7.3 Hz, 2H, H-
0
0
0
0
30,50), 7.72 (t, J7,8 = J7,6 = 7.5 Hz, 1H, H-7), 7.37 (d, J2 ,3 = J6 ,5 = 7.3 Hz,
2H, H-2’,60), 7.22 (d, J5,6 = 7.5 Hz, 1H, H-5), 7.12 (t, J6,5 = J6,7 = 7.5 Hz,
1H, H-6), 7.02 (d, J8,7 = 8.4 Hz, 1H, H-8), EI MS: m/z (rel. abund.%)
249 (M+, 62), 172 (55), 146 (33), 120 (38); Anal. Calcd for
C15H10N2O2: (249) [Found: C, 71.93; H, 4.04; N, 11.18; Requires:
C, 71.99; H, 4.03; N, 11.19].
0
0
0
0
4.13. 2-{[-(4-Oxo-4H-chromen-3-yl) methylidene]
amino}benzoic acid (15)
Yield = 64%; mp = 96 °C; Rf = 0.42 (EtOAc/Hex, 3:7); UV (MeOH);
kmax 232.1 (log
e
= 4.3) nm; IR (KBr): mmax 1646.4 (C@O), 1680.1
(C@N), 3065.9 (ArCH) cmꢀ1
;
1H NMR (400 MHz, CDCl3) d: 8.51 (s,
0
0
1H, H-2), 8.28 (d, J5,6 = 7.6 Hz, 1H, H-5), 8.23 (d, J3 ,4 = 7.3 Hz, 1H,
H-30), 7.80 (dd, J5 ,6 = 1.3 Hz, J5 ,4 = 7.6 Hz, 1H, H-50), 7.49 (t,
J7,8 = J7,6 = 8.5 Hz, 1H, H-7), 7.41 (t, J6,5 = J6,7 = 7.2 Hz, 1H, H-6),
Acknowledgement
0
0
0
0
7.30 (t, J4 ,3 = J4 ,5 = 8.3 Hz, 1H, H-40), 7.01 (d, J8,7 = 7.2 Hz, 1H, H-
This work was supported by the Higher Education Commission
(HEC) Pakistan under the National Research Support Program for
the Universities.
0
0
0
0
8), 6.63 (s, 1H, CH@N), 6.61 (d, J6 ,5 = 7.6 Hz, 2H, H-60); EI MS: m/
z (rel. abund.%) 292 (M+, 22.04), 188 (1.05), 172 (58.29), 120
0
0