INSUASTY ET AL.
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(1E,4E)‐1‐(2‐Butoxy‐7‐chloroquinolin‐3‐yl)‐5‐(4‐hydroxy‐3‐
methoxyphenyl)penta‐1,4‐dien‐3‐one 17l
OCH3). 5.60 (s, 2H, Ph‐CH2), 6.97 (d, J = 7.9 Hz, 1H), 6.99 (d,
J = 15.8 Hz, 1H, ═CH), 7.16 (s, 1H), 7.19 (d, J = 8.1 Hz, 1H), 7.23
(d, J = 5.9 Hz, 1H), 7.45–7.25 (m, 7H), 7.61 (d, J = 5.7 Hz, 1H), 7.74
(d, J = 15.5 Hz, 1H, ═CH), 7.80 (d, J = 15.4 Hz, 1H, ═CH), 7.98 (d,
J = 15.8 Hz, 1H, ═CH), 8.02 (s, 1H). 13C NMR (101 MHz, CDCl3)
δ = 46.6. 56.1, 109.7, 114.9, 115.0, 119.0, 123.4, 123.9, 124.0,
126.3, 126.5, 127.4, 127.7, 129.1, 129.4, 130.8, 135.4, 137.6,
138.2, 140.1, 140.7, 144.0, 146.9, 148.4, 161.0, 189.6 ppm. EI MS
(70 eV): m/z (%): 471 (M+, 3), 294 (10), 91 (100). Anal. calcd. for
Yellow solid, m.p. 130–131°C. FTIR (ATR): ν = 3315 (OH), 1660
.
(C═O) cm−1 1H NMR (400 MHz, CDCl3) δ = 1.08 (t, J = 7.4 Hz, 3H,
CH3), 1.68–1.56 (m, 2H, CH2), 2.00–1.89 (m, 2H, CH2), 3.98 (s, 3H,
OCH3), 4.60 (t, J = 6.6 Hz, 2H, OCH2), 6.95 (d, J = 15.9 Hz, 1H, ═CH),
6.99 (d, J = 8.2 Hz, 1H), 7.14 (d, J = 1.7 Hz, 1H), 7.20 (dd, J = 8.2,
1.8 Hz, 1H), 7.30 (s, 1H), 7.36 (dd, J = 8.6, 2.0 Hz, 1H), 7.45 (d,
J = 16.0 Hz, 1H, ═CH), 7.68 (d, J = 8.7 Hz, 1H), 7.72 (d, J = 16.0 Hz, 1H,
═CH), 7.84 (d, J = 1.9 Hz, 1H), 7.93 (d, J = 16.0 Hz, 1H, ═CH), 8.20 (s,
1H). 13C NMR (101 MHz, CDCl3) δ = 14.0, 19.6, 31.1, 56.0, 66.7,
109.8, 115.0, 120.5, 123.3, 123.6, 123.8, 125.4, 126.3, 127.3, 128.2,
129.0, 136.6, 137.1, 138.2, 143.9, 146.9, 147.4, 148.4, 160.7,
189.1 ppm. EI MS (70 eV): m/z (%): 437 (M+, 3), 204 (14), 129 (16), 57
(99), 43 (100). Anal. calcd. for C25H24ClNO4: C, 68.57; H, 5.52; N,
3.20. Found: C, 68.80; H, 5.25; N, 3.09.
C
28H22ClNO4: C, 71.26; H, 4.70; N, 2.97. Found: C, 71.51; H, 5.01;
N, 3.15.
(1E,4E)‐1‐(2‐(Benzyloxy)‐7‐chloroquinolin‐3‐yl)‐5‐(4‐hydroxy‐3‐
methoxyphenyl)penta‐1,4‐dien‐3‐one 17p
Yellow solid, m.p. 152–153°C. FTIR (ATR): ν = 3320 (OH), 1670
.
(C═O) cm−1 1H NMR (400 MHz, CDCl3) δ = 3.97 (s, 3H, OCH3). 5.68
(s, 2H, Ph‐CH2), 6.01 (s, 1H, OH), 6.87 (d, J = 15.9 Hz, 1H, ═CH). 6.98
(d, J = 8.0 Hz, 1H), 7.08 (s, 1H), 7.10 (d, J = 8.6 Hz, 1H), 7.37 (t,
J = 4.9 Hz, 1H), 7.40 (d, J = 7.5 Hz, 2H), 7.45 (t, J = 7.5 Hz, 2H), 7.50 (d,
J = 16.2 Hz, 1H, ═CH), 7.58 (d, J = 16.3 Hz, 1H, ═CH), 7.62 (d,
J = 7.4 Hz, 2H), 7.71 (d, J = 8.6 Hz, 1H), 7.89 (d, J = 1.6 Hz, 1H, ═CH),
7.94 (d, J = 15.9 Hz, 1H, ═CH), 8.23 (s, 1H). 13C NMR (101 MHz,
CDCl3) δ = 56.0, 68.6, 109.6, 114.9, 120.5, 123.6, 123.8, 124.0, 125.7,
126.4, 127.3, 128.1, 128.3, 128.3, 128.6, 129.1, 136.7, 136.8, 136.9,
138.8, 143.9, 146.9, 147.1, 148.4, 160.3, 189.0 ppm. EI MS (70 eV):
m/z (%): 473/471 (M+, 5/14), 380 (15), 236 (25), 149 (56), 92 (100).
Anal. calcd. for C28H22ClNO4: C, 71.26; H, 4.70; N, 2.97. Found: C,
71.46; H, 4.48; N, 2.72.
1‐Butyl‐6‐chloro‐3‐((1E,4E)‐5‐(4‐methoxyphenyl)‐3‐oxopenta‐1,4‐
dien‐1‐yl)quinolin‐2(1H)‐one 17m
Yellow solid, m.p. 177–179°C. FTIR (ATR) ν = 1649, 1601 (C═O)
cm−1. 1H NMR (CDCl3) δ = 1.06 (t, J = 8.0 Hz, 3H, CH3), 1.50–1.62 (m,
2H, CH2), 1.75–1.83 (m, 2H, CH2), 3.89 (s, 3H, OCH3) 4.36 (t,
J = 8.0 Hz, 2H, NCH2), 6.96 (d, J = 8.0 Hz, 2H), 7.02 (d, J = 16.0 Hz, 1H,
═CH), 7.34 (d, J = 12.0 Hz, 1H), 7.55–7.66 (m, 3H), 7.66 (d, J = 4.0 Hz,
1H), 7.77 (d, J = 16.0 Hz, 1H, ═CH), 7.77 (d, J = 16.0 Hz, 1H, ═CH),
7.90 (d, J = 16.0 Hz, 1H, ═CH), 7.90 (s, 1H) ppm; 13C NMR (101 MHz,
CDCl3) δ = 13.9, 20.4, 29.6, 43.0, 56.1, 114.5, 115.7, 121.5, 123.9,
127.5, 127.6, 127.8, 128.6, 129.7, 130.2, 131.6, 137.5, 137.6, 139.2
143.5, 160.4, 161.7, 189.6 ppm. EI MS (70 eV): m/z (%): 423/421 (M+,
8/21), 260 (76), 204 (66), 161 (45), 133 (59), 84 (100), 48 (17). Anal.
calcd. for C25H24ClNO3: C, 71.17; H, 8.40; N, 3.32. Found: C, 71.30;
H, 8.51; N, 3.21.
(1E,4E)‐1‐(2‐(Benzyloxy)benzo[h]quinolin‐3‐yl)‐5‐(4‐chlorophenyl)‐
penta‐1,4‐dien‐3‐one 17q
.
Yellow solid, m.p. 150–153°C. FTIR (ATR): ν = 1672 (C═O) cm−1 1H
NMR (400 MHz, DMSO‐d6) δ = 5.78 (s, 2H, Ph‐CH2), 7.23 (d,
J = 16.0 Hz, 1H, ═CH), 7.30–8.05 (m, 17H, Ar–H, ═CH), 8.76 (s, 1H),
9.05 (brs, 1H) ppm; 13C NMR (101 MHz, DMSO‐d6) δ = 68.3, 119.1,
122.5, 124.8, 125.7, 126.0, 127.3, 127.5, 128.0, 128.0, 128.4, 128.6,
129.0, 129.1, 129.5, 130.1, 130.6, 134.0, 134.5, 135.6, 136.7, 137.7,
139.2, 142.0, 144.6, 159.3, 188.8 ppm. EI MS (70 eV): m/z (%): 477/
475 (M+, 3/8), 368 (10), 310 (63), 165 (22), 91 (100). Anal. calcd. for
1‐Butyl‐7‐chloro‐3‐((1E,4E)‐5‐(4‐hydroxy‐3‐methoxyphenyl)‐3‐
oxopenta‐1,4‐dien‐1‐yl)quinolin‐2(1H)‐one 17n
Yellow solid, m.p. 194–195°C. FTIR (ATR): ν = 3322 (OH), [1651, 1643]
(C═O) cm−1. 1H NMR (400 MHz, CDCl3) δ = 1.07 (t, J = 7.3 Hz, 3H, CH3),
1.63–1.47 (m, 2H, CH2), 1.85–1.70 (m, 2H, CH2), 3.98 (s, 3H, OCH3),
4.35–4.25 (m, 2H, NCH2), 6.98 (s, 1H), 6.98 (d, J = 15.8.4 Hz, 1H, ═CH),
7.16 (d, J = 6.5 Hz, 1H), 7.18 (d, J = 8.3 Hz, 1H), 7.25 (d, J = 8.0 Hz, 1H),
7.37 (d, J = 1.1 Hz, 1H), 7.59 (d, J = 8.3 Hz, 1H), 7.72 (d, J = 15.8 Hz, 1H,
═CH), 7. 74 (d, J = 15.7 Hz, 1H, ═CH), 7.91 (d, J = 15.8 Hz, 1H, ═CH), 7.93
(s, 1H). 13C NMR (101 MHz, CDCl3) δ = 13.9. 20.4, 29.5, 43.0, 56.1, 109.6,
114.3, 114.9, 119.0, 123.0, 123.9 (×2), 126.2, 127.4, 129.2, 130.8, 137.7,
138.6, 139.8, 140.2, 143.9, 146.9, 148.4, 160.6, 189.6 ppm. EI MS (70 eV):
m/z (%): 437 (M+, 5), 341 (44), 313 (29), 260 (100), 204 (67). Anal. calcd
for C25H24ClNO4: C, 68.57; H, 5.52; N, 3.20. Found: C, 68.81; H, 5.31;
N, 3.03.
C31H22ClNO2: C, 78.23; H, 4.66; N, 2.94. Found: C, 78.04; H, 4.83;
N, 3.10.
(1E,4E)‐1‐(2‐(Benzyloxy)benzo[h]quinolin‐3‐yl)‐5‐(4‐
methoxyphenyl)‐penta‐1,4‐dien‐3‐one 17r
Yellow solid, m.p. 155–157°C; FTIR (ATR): ν = 1647 (C═O) cm−1
.
1H NMR (400 MHz, DMSO‐d6) δ = 3.83 (s, 3H, OCH3), 5.80 (s, 2H,
Ph‐CH2), 7.04 (d, J = 8.0 Hz, 2H), 7.09 (d, J = 16.0 Hz, 1H, ═CH),
7.36 (d, J = 8.0 Hz, 1H), 7.41 (d, J = 16.0 Hz, 1H, ═CH), 7.46 (d,
J = 4.0 Hz, 1H), 7.63–7.78 (m, 8H), 7.84 (d, J = 4.0 Hz, 2H), 7.96 (d,
J = 16.0 Hz, 1H, ═CH), 7.99–8.03 (m, 1H), 8.81 (s, 1H), 9.05–9.10
(m, 1H) ppm; 13C NMR (101 MHz, DMSO‐d6) δ = 55.9, 68.3, 115.0,
119.3, 122.5, 124.7, 124.8, 125.7, 125.9, 127.3, 127.6, 128.1,
128.4, 128.6, 129.0, 129.1, 130.1, 130.9, 134.5, 136.4, 137.7,
1‐Benzyl‐7‐chloro‐3‐((1E,4E)‐5‐(4‐hydroxy‐3‐methoxyphenyl)‐3‐
oxopenta‐1,4‐dien‐1‐yl)quinolin‐2(1H)‐one 17o
Yellow solid, m.p. 190–191°C. FTIR (ATR): ν = 3312 (OH), [1660,
.
1645] (C═O) cm−1 1H NMR (400 MHz, CDCl3) δ = 3.98 (s, 3H,