Thieme
Original Article
(E)-2-(4-bromobenzylidene)-4-hydroxy-2,3-dihydro-1H-
J = 21.2 Hz), 114.24 (s), 28.96 (s). APCI–HRMS m/z calculated for
C16H12FO2 (MH+ ): 255.0816, found: 255.0816. Purity (HPLC): 100%.
inden-1-one (2 k)
The title compound (gold crystals) was prepared in a yield of 49%
from 4-hydroxy-2,3-dihydro-1H-inden-1-one and 4-bromobenza-
ldehyde: mp 30.9–31.0 °C (EtOH); 1H NMR (600 MHz, DMSO) δ
10.14 (d, J = 13.7 Hz, 1 H), 7.72 (qd, J = 8.4, 2.6 Hz, 4 H), 7.49 (d,
J=1.8Hz, 1H), 7.31 (td, J=7.7, 1.5Hz, 1H), 7.25 (d, J=7.5Hz, 1H),
7.10 (d, J = 7.8 Hz, 1 H), 3.91 (s, 2 H); 13C NMR (151 MHz, DMSO) δ
193.53, 154.85, 138.76, 136.33, 135.90, 134.17, 132.58, 132.01,
131.51, 129.15, 123.31, 120.54, 114.19, 28.99. APCI–HRMS m/z
calculated for C16H12BrO2 (MH+ ): 315.0015, found: 315.0015. Pu-
rity (HPLC): 100 %.
(E)-2-(4-fluorobenzylidene)-4-hydroxy-2,3-dihydro-1H-
inden-1-one (2 g)
The title compound (light brown crystals) was prepared in a yield
of 44% from 4-hydroxy-2,3-dihydro-1H-inden-1-one and 4-fluoro-
benzaldehyde: mp 51.5–51.6 °C (EtOH); 1H NMR (600MHz, DMSO)
δ 10.12 (s, 1H), 7.86 (dd, J=8.4, 5.7Hz, 2H), 7.52 (s, 1H), 7.33 (dt,
J=15.2, 8.2Hz, 3H), 7.25 (d, J=7.4Hz, 1H), 7.10 (d, J=7.7Hz, 1H),
3.91 (s, 2H); 13C NMR (151MHz, DMSO) δ 193.55, 163.56, 161.91,
154.82, 138.83, 136.33, 134.78 (d, J=2.2Hz), 133.06 (d, J=8.6Hz),
131.64, 131.59 (d, J = 3.1 Hz), 129.09, 120.42, 116.15, 116.01,
114.15, 28.90. APCI–HRMS m/z calculated for C16H12FO2 (MH+ ):
255.0816, found: 255.0816. Purity (HPLC): 98.1 %.
(E)-4–hydroxy-2-(4-(trifluoromethyl)benzylidene)-2,3-
dihydro-1H-inden-1–one (2 l)
The title compound (green crystals) was prepared in a yield of 39%
from 4-hydroxy-2,3-dihydro-1H-inden-1-one and 4-(trifluorome-
thyl)benzaldehyde: mp 317.3–397.4 °C (EtOH); 1H NMR (600MHz,
DMSO) δ 10.18 (d, J = 4.9 Hz, 1 H), 7.99 (d, J = 8.1 Hz, 2 H), 7.85 (d,
J = 8.2 Hz, 2 H), 7.57 (s, 1 H), 7.31 (t, J = 7.6 Hz, 1 H), 7.26 (d,
J = 7.4 Hz, 1 H), 7.11 (d, J = 7.7 Hz, 1 H), 3.96 (s, 2 H); 13C NMR
(151 MHz, DMSO) δ 193.50, 154.90, 138.94, 138.61, 137.66,
136.50, 131.19, 130.92, 129.36, 129.22, 129.15, 125.75 (dd,
J=7.3, 3.5Hz), 125.00, 123.20, 120.69, 114.27, 28.96. APCI–HRMS
m/z calculated for C17H12F3O2 (MH+ ): 305.0784, found: 305.0807.
Purity (HPLC): 98.4 %.
(E)-2-(3-chlorobenzylidene)-4-hydroxy-2,3-dihydro-1H-
inden-1-one (2 h)
The title compound (beige powder) was prepared in a yield of 75%
from 4-hydroxy-2,3-dihydro-1H-inden-1-one and 3-chlorobenza-
ldehyde: mp 386.7–386.8 °C (EtOH); 1H NMR (600 MHz, DMSO) δ
10.14 (s, 1 H), 7.85 (s, 1 H), 7.77 (d, J = 7.4 Hz, 1 H), 7.58–7.48 (m,
3H), 7.32 (t, J=7.6Hz, 1H), 7.26 (d, J=6.9Hz, 1H), 7.11 (dd, J=7.8,
0.8 Hz, 1 H), 3.95 (d, J = 1.5 Hz, 2 H); 13C NMR (151 MHz, DMSO) δ
193.46, 154.82, 138.65, 137.10, 136.60, 136.38, 133.68, 131.15,
130.79, 129.95, 129.41, 129.24, 129.15, 120.63, 114.23, 39.52,
28.91. APCI–HRMS m/z calculated for C16H12ClO2 (MH+ ): 271.0520,
found: 271.0520. Purity (HPLC): 100 %.
(E)-4-((4-hydroxy-1-oxo-1H-inden-2(3 H)-ylidene)methyl)
benzonitrile (2 m)
(E)-2-(4-chlorobenzylidene)-4-hydroxy-2,3-dihydro-1H-
inden-1-one (2 i)
The title compound (green crystals) was prepared in a yield of 53%
from 4-hydroxy-2,3-dihydro-1H-inden-1-one and 4-formylbenzo-
nitrile: mp 304.5–307.4 °C (MeOH); 1H NMR (600 MHz, DMSO) δ
10.17 (s, 1H), 7.95 (s, 4H), 7.54 (d, J=1.8Hz, 1H), 7.31 (t, J=7.6Hz,
1 H), 7.25 (d, J = 7.4 Hz, 1 H), 7.11 (d, J = 7.6 Hz, 1 H), 3.95 (s, 2 H);
13C NMR (151 MHz, DMSO) δ 193.40, 154.86, 139.48, 138.51,
138.25, 136.43, 132.69, 131.13, 130.70, 129.21, 120.74, 118.66,
114.26, 111.52, 29.00. APCI–HRMS m/z calculated for C17H12NO2
(MH+ ): 262.0863, found: 262.0857. Purity (HPLC): 96.6 %.
The title compound (gold crystals) was prepared in a yield of 61%
from 4-hydroxy-2,3-dihydro-1H-inden-1-one and 4-chlorobenza-
ldehyde: mp 30.9–31.0 °C (EtOH); 1H NMR (600 MHz, DMSO) δ
10.14 (d, J=10.6Hz, 1H), 7.81 (d, J=8.4Hz, 2H), 7.57 (d, J=8.4Hz,
2 H), 7.50 (s, 1 H), 7.30 (t, J = 7.6 Hz, 1 H), 7.24 (d, J = 7.4 Hz, 1 H),
7.10 (d, J = 7.8 Hz, 1 H), 3.91 (s, 2 H); 13C NMR (151 MHz, DMSO) δ
193.53, 154.86, 138.77, 136.33, 135.78, 134.42, 133.85, 132.38,
131.42, 129.14, 129.07, 120.53, 114.19, 28.98. APCI–HRMS m/z
calculated for C16H12ClO2 (MH+ ): 271.0520, found: 271.0520. Pu-
rity (HPLC): 100 %.
(E)-2((2-aminopyrimidine-5-yl)methylene)-4-hydroxy-2,3-
dihydro-1H–inden-1-one (2 n)
The title compound (beige powder) was prepared in a yield of 10%
from 4-hydroxy-2,3-dihydro-1H-inden-1-one and 2-aminopyrimi-
dine-5-carbaldehyde: mp 398.5–398.8 °C (MeOH); 1H NMR
(600MHz, DMSO) δ 10.05 (s, 1H), 8.67 (s, 2H), 7.38–7.26 (m, 4H),
(E)-2-(3-bromobenzylidene)-4-hydroxy-2,3-dihydro-1H-
inden-1–one (2 j)
The title compound (beige powder) was prepared in a yield of 68%
from 4-hydroxy-2,3–dihydro-1H-inden-1-one and 3-bromoben-
zaldehyde: mp 30.8–30.9 °C (EtOH); 1H NMR (600 MHz, DMSO) δ
10.15 (d, J = 4.8 Hz, 1 H), 7.97 (s, 1 H), 7.80 (d, J = 7.8 Hz, 1 H), 7.64
(dd, J=7.9, 1.1Hz, 1H), 7.53–7.44 (m, 2H), 7.31 (t, J=7.6Hz, 1H),
7.25 (d, J=7.3Hz, 1H), 7.13–7.08 (m, 1H), 3.93 (d, J=1.3Hz, 2H);
13C NMR (151 MHz, DMSO) δ 193.48, 154.86, 138.68, 137.40,
136.59, 136.40, 132.86, 132.33, 131.13, 131.06, 129.60, 129.17,
122.31, 120.66, 114.24, 28.91. APCI–HRMS m/z calculated for
C16H12BrO2 (MH+ ): 315.0015, found: 315.0015. Purity (HPLC): 100%.
7.22 (d, J = 7.3 Hz, 1 H), 7.08 (d, J = 7.7 Hz, 1 H), 3.87 (s, 2 H); 13
C
NMR (151MHz, DMSO) δ 193.09, 162.95, 160.38, 154.74, 139.21,
135.83, 131.74, 129.00, 128.27, 120.20, 117.94, 114.07, 39.52,
29.19. APCI–HRMS m/z calculated for C14H12N3O2 (MH+ ):254.0924,
found: 254.0924. Purity (HPLC): 76 %.
(E)-4-hydroxy-2-(pyridin-2-ylmethylene)-2,3-dihydro-1H-
inden-1-one (2 o)
The title compound (green powder) was prepared in a yield of 71%
from 4-hydroxy-2,3-dihydro–1H-inden-1-one and picolinaldehyde:
mp 30.8–30.9 °C (H2O); 1H NMR (600MHz, DMSO) δ 10.28 (s, 1H),
8.85 (dd, J = 4.9, 0.8 Hz, 1 H), 8.16 (t, J = 7.4 Hz, 1 H), 8.04 (d,
Janse van Rensburg HD et al. Indanones on Adenosine Receptors… Drug Res