988
BENTAHAR et al.
All reagents were purchased from Aldrich. Solvents
spectrum (300 MHz, CDCl3), δ, ppm: 7.95 d (2H,
HAr), 7.69 d (1H, HC=C), 7.53 d.d (3H, HAr), 7.45 d
(2H, HAr), 7.45 d (1H, HC=C), 7.33 d (2H, HAr); FTIR
(ATR, cm–1) 3123–2970 (C–HAr, C–Halkene), 1781
(C=O), 1579 (C=Calkene), 1482 (C=CAr).
were distilled before use. The reactions were monitored
by layer chromatography (TLC). Nuclear magnetic
resonance (NMR) spectra were obtained on a Bruker
Model Avance DMX 300 Spectrometer in CDCl3 using
TMS as an internal standard. Infrared spectra were
run on a JASCO 4100 spectrometer. Melting points
were taken on Kofler bench, type Wagner & Munz
HEIZBANK. The revelation was carried out using the
CAUTION Ultra-Violet lamp (254 and 365 nm).
3-(3-Nitrophenyl)-1-phenylpropenone 3ae. Yellow
1
solid, 90% yield, mp: 144–146°C. H NMR spectrum
(300 MHz, CDCl3), δ, ppm: 8.55 s (1H, HAr), 8.29 d
(1H, HAr), 8.08 d (1H, HAr), 7.95 d (2H, HAr), 7.86 d
(1H, HC=C), 7.68 d (1H, HC=C), 7.65 m (3H, HAr), 7.56
t (1H, HAr); FTIR (ATR, cm–1) 3032–2921 (C–HAr, C–
Halkene), 1732 (C=O), 1586 (C=Calkene), 1544 (C=CAr),
1398 (C–NO2).
General procedure for the synthesis of chalcones.
The condensation reaction was carried out by reacting
an equimolar mixture of aromatic benzaldehyde
and acetophenone or 2-acetylfuran in methanol in
the presence of KF-modified clay (30 mg) at room
temperature (Scheme 1). The progress of the reaction
is monitored by thin-layer chromatography every
five minutes. At the end of the reaction, the product
precipitates. It is then taken up in dichloromethane (2 ×
10 mL). The organic phase is dried over Na2SO4 and
the solvent is evaporated using a rotary evaporator. The
product is then purified by recrystallization from ethanol
and characterized by FTIR, 1H NMR, and 13C NMR.
1-Furan-2-yl-3-phenylpropenone 3ba. Brown
1
solid, 99% yield, mp: 88–90°C. H NMR spectrum,
δ, ppm: 7.92 d (1H, HC=C), 7.68 m (3H, HAr), 7.57 d
(1H, HC=C), 7.46 d (1H, Hpyr + d, 2H, HAr), 7.36 d (1H,
Hpyr), 6.62 d.d (1H, Hpyr); 13C NMR spectrum (75 MHz,
DMSO-d6), δ, ppm: 178, 153.5, 147, 144, 134.9, 130.5,
129.5, 128.5, 121.5, 117.5, 112; FTIR (ATR, cm–1)
3158–3018 (C–HAr, C–Halkene), 1607 (C=O), 1572
(C=Calkene), 1454 (C=CAr), 1405, 1015 (C–Oether).
1-Furan-2-yl-3-(4-methoxyphenyl)propenone
3bb. Pale yellow solid; 97% yield; mp 96–98°C;
1H NMR spectrum (300 MHz, CDCl3), δ, ppm: 7.88 d
(1H, HC=C), 7.67 d (1H, Hpyr), 7.64 d ( 2H, HAr),
7.37 d (1H, HC=C), 7.34 d (1H, Hpyr), 6.98 d (2H, HAr),
6.62 d.d (1H, Hpyr), 3.9 s (3H, CH3); 13C NMR spectrum
(75 MHz, DMSO-d6), δ, ppm: 178.5, 161, 154, 146.5,
143.5, 130.5, 127.5, 119, 117.5, 114.5, 112.5, 55; FTIR
(ATR, cm–1) 3199, 3095 (C–HAr), 3032 (C–Halkene),
Benzalacetophenone 3aa. pale yellow solid, 93%
1
yield, mp 55–57°C. H NMR spectrum (300 MHz,
CDCl3), δ, ppm: 8.17 d (2H, HAr), 7.95 d (1H, HC=C),
7.91 d (2H, HAr), 7.77 d (1H, HC=C), 7.67 t (1H, HAr), 7.59 t
(2H, HAr), 7.57 m (3H, HAr). FTIR (ATR, cm–1) 3123–
2950 (C–HAr, C–Halkene), 1700-1475 (C=O, C=Calkene
,
C=CAr).
3-(4-Methoxyphenyl)-1-phenylpropenone
3ab.
1
2998 (C–HCH ), 1593 (C=O), 1520 (C=Calkene), 1457
Yellow solid; 91% yield; mp 73–75°C; H NMR
spectrum (300 MHz, CDCl3), δ, ppm: 8.16 d (2H, HAr),
7.87 d (2H, HAr), 7.84 d (1H, HC=C), 7.73 d (1H, HC=C),
7.67 t (1H, HAr), 7.59 t (2H, HAr), 7.11 d (2H, HAr), 3.8 s
(3H, CH3). FTIR (ATR, cm–1) 3081–2989 (C–HAr, C–
3
(C=CAr), 1002 (C–Oether).
1-Furan-2-yl-3-p-tolylpropenone 3bc. Brown
1
solid, 95% yield, mp 112–114°C. H NMR spectrum
(300 MHz, CDCl3): δ 7.88 d (1H, CHC=C), 7.67 d (1H,
Hpyr), 7.57 d (2H, HAr), 7.44 d (1H, HC=C), 7.34 d (1H,
Hpyr), 7.25 d (2H, HAr), 6.62 d.d (1H, Hpyr), 2.4 s (3H,
CH3); 13C NMR spectrum(75 MHz, DMSO-d6), δ, ppm:
178.5, 153.5, 146.5, 144.5, 140.5, 132, 129.5, 129,
120.5, 117.5, 112.5, 21.5; FTIR (ATR, cm–1) 3158–3005
(C–HAr, C–Halkene), 2900 (C–HCH3), 1565 (C=O), 1517
(C=Calkene), 1482 (C=CAr), 1002 (C–Oether).
H
alkene), 2934 (C–HCH ), 1697 (C=O), 1624 (C=Calkene),
3
1534 (C=CAr), 1009 (C–Oether).
1-Phenyl-3-p-tolylpropenone 3ac. Yellow solid,
91% yield, mp 96–98°C. 1H NMR spectrum (300 MHz,
CDCl3), δ, ppm: 7.95 d (2H, HAr), 7.78 d (1H, HC=C),
7.46 m (5H, HAr), 7.46 d (1H, HC=C), 7.17 d (2H, HAr),
2.31 s (3H, CH3). FTIR (ATR, cm–1) 3083–2991 (C–
HAr, C–Halkene), 2914 (C–HCH3), 1700 (C=O), 1614
(C=Calkene), 1544 (C=CAr).
3-(4-Chloro-phenyl)-1-furan-2-yl-propenone
1
3bd. White solid, 98% yield, mp 141–143°C. H NMR
3-(4-Chloro-phenyl)-1-phenyl-propenone
Yellow solid, 90% yield, mp 111–113°C. H NMR
3ad.
spectrum (300 MHz, CDCl3), δ, ppm: 7.85 d (1H,
HC=C), 7.68 d (1H, Hpyr), 7.6 d (2H, HAr), 7.45 d (1H,
1
RUSSIAN JOURNAL OF APPLIED CHEMISTRY Vol. 93 No. 7 2020