H. Nadri et al. / Bioorg. Med. Chem. 18 (2010) 6360–6366
6365
yield, mp 244–247 °C, IR
m
max/cmꢁ1 (KBr): 1705 (C@O), 1637 (C@C
dine, J = 6.80 Hz), 8.52 (d, 2H, Hb-pyridine, J = 6.55 Hz), 7.76 (d,
1H, H4, J = 8.6 Hz), 7.65–7.62 (m, 1H, Ph), 7.54–7.52 (m, 1H, Ph),
7.34–7.31 (m, 2H, Ph), 7.14 (d, 1H, H7, J = 2.4 Hz), 7.06 (s, 1H,
C@CH), 6.88 (dd, 1H, H5, J = 8.6 Hz, J = 2.4 Hz), 5.97 (s, 2H,
–CH2N), 4.15 (t, 2H, OCH2, J = 6.5 Hz), 1.79 (m, 2H, –CH2–), 1.00
(t, 2H, –CH3, J = 6.5 Hz). Anal. Calcd for C24H21ClFNO3: C, 67.69;
H, 4.97; N, 3.29. Found: C, 67.78; H, 4.99; N, 3.30. EI-MS m/z (%)
390 (M+, 5), 383 (23), 314 (24), 136 (40), 109 (70), 43 (100).
alkene), 1H NMR (DMSO-d6, 500 MHz), 9.23 (d, 2H, Ha-pyridine,
J = 6.45 Hz), 8.52 (d, 2H, Hb-pyridine, J = 6.45 Hz), 7.77 (d, 1H, H4,
J = 8.5 Hz), 7.36–7.28 (m, 3H, Ph), 7.25 (s, 1H, Ph), 7.16 (d, 1H, H7,
J = 2 Hz), 7.04 (s, 1H, C@CH), 6.95 (dd, 1H, H5, J = 8.5 Hz, J = 2 Hz),
5.82 (s, 2H, –CH2N), 4.23 (q, 2H, OCH2, J = 6.8 Hz), 2.3 (s, 3H,
–CH3), 1.41 (t, 3H, –CH3, J = 6.8 Hz). Anal. Calcd for C24H22ClNO3:
C, 70.67; H, 5.44; N, 3.43. Found: C, 70.92; H, 5.44; N, 3.42. EI-MS
m/z (%) 372 (M+, 6), 321 (46), 255 (40), 199 (50), 105 (12), 83
(33), 55 (88), 43 (100).
4.1.27. (Z)-1-(2-Methylbenzyl)-4-((6-propoxy-3-oxobenzofuran-
2(3H)-ylidene) methyl) pyridinium chloride (6s)
4.1.23. (Z)-1-(2-Fluorobenzyl)-4-((6-ethoxy-3-oxobenzofuran-
2(3H)-ylidene) methyl) pyridinium chloride (6i)
Starting from (Z)-6-propoxy-2-(pyridin-4-ylmethylene)benzo-
furan-3(2H)-one (1 mmol, 0.281 g) and 2-methylbenzyl chloride
(1.2 mmol, 0.169 g), compound 6s was obtained, quantitative yield,
Starting from (Z)-6-ethoxy-2-(pyridin-4-ylmethylene)benzofu-
ran-3(2H)-one (1 mmol, 0.267 g) and 2-fluorobenzyl chloride
(1.2 mmol, 0.173 g), compound 6i was obtained, quantitative yield,
mp 225–228 °C, IR m
max/cmꢁ1 (KBr): 1705 (C@O), 1644 (C@C alke-
ne),1H NMR (DMSO-d6, 500 MHz), 9.09 (d, 2H, Ha-pyridine,
J = 6.35 Hz), 8.55 (d, 2H, Hb-pyridine, J = 6.30 Hz), 7.77 (d, 1H, H4,
J = 8.55 Hz), 7.34–7.32 (m, 2H, Ph), 7.30 (d, 1H, H7, J = 2.1 Hz),
7.18–7.16 (m, 2H, Ph), 7.08 (s, 1H, C@CH), 6.95 (dd, 1H, Hz, H5,
J = 8.55, J = 2.1 Hz), 5.94 (s, 2H, –CH2N), 4.15 (t, 2H, OCH2,
J = 6.5 Hz), 2.33 (s, 3H, –CH3), 1.79 (m, 2H, –CH2–), 1.00 (t, 2H,
–CH3, J = 6.5 Hz). Anal. Calcd for C25H24ClNO3: C, 71.17; H, 5.73;
N, 3.32. Found: C, 70.90; H, 5.71; N, 3.31. EI-MS m/z (%) 386 (M+,
6), 281 (48), 238 (82), 105 (100), 79 (22), 43 (16).
mp 226–230 °C, IR m
max/cmꢁ1 (KBr): 1709 (C@O), 1635 (C@C al-
kene), 1H NMR (DMSO-d6, 500 MHz), 9.18 (d, 2H, Ha-pyridine,
J = 6.4 Hz), 8.54 (d, 2H, Hb-pyridine, J = 6.5 Hz), 7.76 (d, 1H, H4,
J = 8.6 Hz), 7.66–7.63 (m, 1H, Ph), 7.54–7.52 (m, 1H, Ph), 7.36–
7.33 (m, 2H, Ph), 7.16 (d, 1H, H7, J = 2.1 Hz), 7.04 (s, 1H, C@CH),
6.91 (dd, 1H, H5, J = 8.6 Hz, J = 2.1 Hz), 5.99 (s, 2H, –CH2N), 4.25
(q, 2H, OCH2, J = 6.8 Hz), 1.39 (t, 3H, –CH3, J = 6.8 Hz). Anal. Calcd
for C23H19ClFNO3: C, 67.07; H, 4.65; N, 3.40. Found: C, 67.14; H,
4.63; N, 3.42. EI-MS m/z (%) 376 (M+, 5), 369 (17), 267 (32) 238
(54), 109 (100), 63 (14).
4.1.28. (Z)-1-(4-Methylbenzyl)-4-((6-propoxy-3-oxobenzofuran-
2(3H)-ylidene) methyl) pyridinium chloride (6u)
4.1.24. (Z)-1-(3-Fluorobenzyl)-4-((6-ethoxy-3-oxobenzofuran-
2(3H)-ylidene) methyl) pyridinium chloride (6j)
Starting from (Z)-6-propoxy-2-(pyridin-4-ylmethylene) benzo-
furan-3(2H)-one (1 mmol, 0.281 g) and 4-methylbenzyl chloride
(1.2 mmol, 0.169 g), compound 6u was obtained, quantitative
Starting from (Z)-6-ethoxy-2-(pyridin-4-ylmethylene)benzofu-
ran-3(2H)-one (1 mmol, 0.267 g) and 3-fluorobenzyl chloride
(1.2 mmol, 0.173 g), compound 6j was obtained, quantitative yield,
yield, mp 234–238 °C, IR
m
max/cmꢁ1 (KBr): 1709 (C@O), 1640
(C@C alkene), 1H NMR (DMSO-d6, 500 MHz), 9.19 (d, 2H, Ha-pyri-
dine, J = 6.55 Hz), 8.51 (d, 2H, Hb-pyridine, J = 6.50 Hz), 7.77 (d,
1H, H4, J = 8 Hz), 7.45 (d, 2H, Ph, J = 7.9 Hz), 7.27 (d, 2H, Ph,
J = 7.9 Hz), 7.17 (d, 1H, H7, J = 2 Hz), 7.04 (s, 1H, C@CH), 6.93 (dd,
1H, H5, J = 8 Hz, J = 2 Hz), 5.8 (s, 2H, –CH2N), 4.15 (t, 2H, OCH2,
J = 6.5 Hz), 2.31 (s, 3H, –CH3), 1.79 (m, 2H, –CH2–), 1.00 (t, 2H,
–CH3, J = 6.5 Hz). Anal. Calcd for C25H24ClNO3: C, 71.17; H, 5.73;
N, 3.32. Found: C, 71.34; H, 5.73; N, 3.30. EI-MS m/z (%) 386 (M+,
9), 281 (50), 238 (84), 105 (100), 79 (22), 43 (15).
mp 230–233 °C, IR m
max/cmꢁ1 (KBr): 1707 (C@O), 1643 (C@C al-
kene), 1H NMR (DMSO-d6, 500 MHz), 9.17 (d, 2H, Ha-pyridine,
J = 6.8 Hz), 8.53 (d, 2H, Hb-pyridine, J = 6.8 Hz), 7.77 (d, 1H, H4,
J = 8.5 Hz), 7.52–7.50 (m, 2H, Ph), 7.43–7.41 (m, 1H, Ph), 7.30–
7.27 (m, 1H, Ph), 7.2 (d, 1H, H7, J = 2 Hz), 7.04 (s, 1H, C@CH), 6.96
(dd, H5, 1H, J = 8.5 Hz, J = 2 Hz), 5.91 (s, 2H, –CH2N), 4.25 (q, 2H,
OCH2, J = 6.8 Hz), 1.39 (t, 3H, –CH3, J = 6.8 Hz). Anal. Calcd for
C
23H19ClFNO3: C, 67.07; H, 4.65; N, 3.40. Found: C, 66.89; H,
4.66; N, 3.41. EI-MS m/z (%) 376 (M+, 8), 369 (17), 267 (36) 238
(51), 109 (100), 63 (23).
4.1.29. (Z)-1-(3-Fluorobenzyl)-4-((6-propoxy-3-oxobenzofuran-
2(3H)-ylidene) methyl) pyridinium chloride (6q)
4.1.25. (Z)-1-(2-Methylbenzyl)-4-((6-ethoxy-3-oxobenzofuran-
2(3H)-ylidene) methyl) pyridinium chloride (6l)
Starting from (Z)-6-propoxy-2-(pyridin-4-ylmethylene)benzo-
furan-3(2H)-one (1 mmol, 0.281 g) and 3-fluorobenzyl chloride
(1.2 mmol, 0.173 g), compound 6q was obtained, quantitative
Starting from (Z)-6-ethoxy-2-(pyridin-4-ylmethylene)benzofu-
ran-3(2H)-one (1 mmol, 0.267 g) and 2-methylbenzyl chloride
(1.2 mmol, 0.169 g), compound 6l was obtained, quantitative yield,
yield, mp 224–227 °C, IR
m
max/cmꢁ1 (KBr): 3011 1705 (C@O),
1642 (C@C alkene), 1H NMR (DMSO-d6, 500 MHz), 9.25 (d, 2H,
Ha-pyridine, J = 6.8 Hz), 8.53 (d, 2H, Hb-pyridine, J = 6.8 Hz), 7.76
(d, 1H, H4, J = 8.6 Hz), 7.53–7.50 (m, 2H, Ph), 7.43–7.41 (m, 1H,
Ph), 7.29–7.26 (m, 1H, Ph), 7.2 (d, 1H, H7, J = 2 Hz), 7.04 (s, 1H,
C@CH), 6.93 (dd, 1H, H5, J = 8.6 Hz, J = 2 Hz), 5.91 (s, 2H, –CH2N),
4.15 (t, 2H, OCH2, J = 6.5 Hz), 1.79 (m, 2H, –CH2–), 1.00 (t, 2H,
–CH3, J = 6.5 Hz). Anal. Calcd for C24H21ClFNO3: C, 67.69; H, 4.97;
N, 3.29. Found: C, 67.86; H, 4.95; N, 3.30. EI-MS m/z (%) 390 (M+,
5), 383 (20), 314 (23), 136 (43), 109 (70), 43 (100).
mp 228–231 °C, IR m
max/cmꢁ1 (KBr): (C@O), 1637 (C@C alkene), 1H
NMR (DMSO-d6, 500 MHz), 9.09 (d, 2H, Ha-pyridine, J = 6.85 Hz),
8.55 (d, 2H, Hb-pyridine, J = 6.80 Hz), 7.77 (d, 1H, H4, J = 8.5 Hz),
7.36–7.35 (m, 2H, Ph), 7.33 (d, 1H, H7, J = 2.2 Hz), 7.18–7.15 (m,
2H, Ph), 7.08 (s, 1H, C@CH), 6.94 (dd, 1H, H5, J = 8.5 Hz,
J = 2.2 Hz), 5.94 (s, 2H, –CH2N), 4.25 (q, 2H, OCH2, J = 6.8 Hz), 2.33
(s, 3H, –CH3), 1.39 (t, 3H, –CH3, J = 6.8 Hz). Anal. Calcd for
C
24H22ClNO3: C, 70.67; H, 5.44; N, 3.43. Found: C, 70.43; H, 5.45;
N, 3.43. EI-MS m/z (%) 372 (M+, 8), 321 (34), 255 (46), 199 (54),
105 (14), 83 (35), 55 (86), 43 (100).
4.1.30. (Z)-1-(3-Methylbenzyl)-4-((6-propoxy-3-oxobenzofuran-
2(3H)-ylidene) methyl) pyridinium chloride (6t)
4.1.26. (Z)-1-(2-Fluorobenzyl)-4-((6-propoxy-3-oxobenzofuran-
2(3H)-ylidene) methyl) pyridinium chloride (6p)
Starting from (Z)-6-propoxy-2-(pyridin-4-ylmethylene)benzo-
furan-3(2H)-one (1 mmol, 0.281 g) and 3-methylbenzyl chloride
(1.2 mmol, 0.169 g), compound 6t was obtained, quantitative yield,
Starting from (Z)-6-propoxy-2-(pyridin-4-ylmethylene)benzo-
furan-3(2H)-one (1 mmol, 0.281 g) and 2-fluorobenzyl chloride
(1.2 mmol, 0.173 g), compound 6p was obtained, quantitative
mp 238–241 °C, IR m
max/cmꢁ1 (KBr): 1704 (C@O), 1645 (C@C al-
kene), 1H NMR (DMSO-d6, 500 MHz), 9.2 (d, 2H, Ha-pyridine,
J = 6.4 Hz), 8.5 (d, 2H, Hb-pyridine, J = 6. 5 Hz), 7.75 (d, 1H, H4,
J = 8.5 Hz), 7.33–7.29 (m, 3H, Ph), 7.21 (s, 1H, Ph), 7.16 (d, 1H, H7,
yield, mp 222–225 °C, IR
(C@C alkene), 1H NMR (DMSO-d6 500 MHz), 9.26 (d, 2H, Ha-pyri-
m
max/cmꢁ1 (KBr): 1701 (C@O), 1643