Synthesis and characterisation of novel 3-(4-benzoyl-5-phenylfuran-2-yl) coumarins

Article abstract of DOI:10.3184/174751918X15380427556768

Novel 3-(4-benzoyl-5-phenylfuran-2-yl)coumarin derivates were synthesised via a simple three-step reaction from salicylic aldehydes, ethyl 3-oxobutanoate and 1,3-diphenylpropane-1,3-dione. The synthesised compounds were characterised by NMR, MS and elemental analyses and single-crystal X-ray diffraction analysis.

Full text of DOI:10.3184/174751918X15380427556768

508 RESEARCH PAPER
VOL. 42 OCTOBER, 508–511
JOURNAL OF CHEMICAL RESEARCH 2018
Synthesis and characterisation of novel 3-(4-benzoyl-5-phenylfuran-2-yl)
coumarins
Wang Weidong, Zhao Fang, Hu Yang, Li Qiao and Hu Shengli*
Hubei Collaborative Innovation Center for Rare Metal Chemistry, Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, College of Chemistry and
Chemical Engineering, Hubei Normal University, Huangshi 435002, P.R. China
Novel 3-(4-benzoyl-5-phenylfuran-2-yl)coumarin derivates were synthesised via a simple three-step reaction from salicylic aldehydes,
ethyl 3-oxobutanoate and 1,3-diphenylpropane-1,3-dione. The synthesised compounds were characterised by NMR, MS and elemental
analyses and single-crystal X-ray diffraction analysis.
Keywords: coumarin, furan, I2/CuO, coupling/cyclisation
Coumarins are important and well-known naturally
occurring oxygen-heterocyclic compounds that play a key
role in the medicinal field due to their structural diversity
and pharmaceutical properties. Various synthetic coumarin
derivatives constitute one of the most widely used groups
of anti-HIV,1,2 anticoagulant,3 anti-inflammatory4–6 and
antioxidant7,8 agents. They have been extensively studied
for decades to exert other valuable biological effects such as
anticancer9–13 and antiviral14 activities. Furans represent one of
the most versatile and important classes of heterocycles, and are
present in many natural products and biologically active drug
molecules.15–21 Compounds that have a multi-substituted furan
ring as their main component or have a furan ring fused with
other rings have exhibited a vast array of activity.22 Moreover,
the combination of two or more different heterocyclic moieties
in a single molecule would significantly enhance biological
activity.23,24
have better biological activity than existing biologically active
molecules.
First, various substituted 3-acetylcoumarins (3a–f) were
easily synthesised from ethyl acetoacetate and different
salicylic aldehydes by a Knoevenagel condensation/cyclisation
tandem process. Second, 3-acetylcoumarins (3a–f) were
allowed to react with 1,3-diphenylpropane-1,3-dione in DMSO
under the media of I2/CuO to afford 1,4-enediones 5a–f.
Finally, compounds 5a–f were converted into compounds 6a–f
by a reduction and cyclisation reaction in good yields (71–77%).
The structures of all compounds 6a–f were established by
spectroscopic techniques (NMR, MS and elemental analyses).
For compound 6f, the ESI-MS spectrum gave a molecular ion
peak at m/z 949.08, which was in agreement with [2M + Na]+.
1
In the H NMR spectrum of 6f, the triplet peak at δ 1.22 ppm
and quartet peak at δ 3.43 ppm corresponded to the –CH3 and
–CH2– protons, respectively. The single peak at δ 8.12 ppm
corresponded to the –CH=C–COO– proton of the coumarin
unit. The presence of other signals corresponded to the aromatic
protons of the benzene cycle and furan cycle. The 13C NMR
spectrum of 6f exhibited the presence of –CH3 and –CH2–
carbons at δ 12.5 ppm and 44.9 ppm, respectively. The signal at
δ 191.7 ppm was assigned to the carbonyl carbon of Ph–C=O.
Considering the above facts, herein, we report the synthesis
of
a
series of novel 3-(4-benzoyl-5-phenylfuran-2-yl)
coumarins from readily available salicylic aldehydes, ethyl
3-oxobutanoate and 1,3-diphenylpropane-1,3-dione via a
simple three-step reaction (Scheme 1). We expect these new
compounds comprising of coumarin and furan moieties to
O
O
O
R1
O
R1
R2
CHO
OH
2
R2
O
O
Piperidine
R3
3a-f
R3
1a-f
a: R1 =R2 =R3 =H;
b: R1 = CH3, R2 =R3= H
c: R1 =H, R2=H, R3=OCH3
d: R1 =Cl, R2 =R3=H
e: R1 = Br, R2=R3=H;
f: R1 =R3=H; R2=NEt2
O
O
I2 /CuO,
DMSO
4
O
O
O
R1
SnCl2
AcOH, HCl
R1
R2
O
O
R2
O
O
O
O
R3
5a-f
R3
6a-f
Scheme 1 Synthetic route for 3-(4-benzoyl-5-phenylfuran-2-yl)coumarins 6a–f.
* Correspondent. E-mail: hushengli168@126.com

JOURNAL OF CHEMICAL RESEARCH 2018 509
Furthermore, the structure of the product was confirmed by
X-ray diffraction analysis of 6a (Fig. 1).
These compounds were characterised by IR, NMR, MS and
elemental analyses. The structure of compound 6a was further
confirmed by single crystal X-ray diffraction analysis. These
new heterocyclic compounds may be beneficially used in drug
research.
A
possible reaction mechanism (Scheme 2) using
3-acetylcoumarin 3a as an example is as follows:
3-acetylcoumarin 3a could be transformed to coumarin-3-
yl-glyoxal B via a domino iodinatione Kornblum oxidation
reaction,25,26 which could further undergo Knoevenagel-type
condensation with 1,3-diphenylpropane-1,3-dione 4 to generate
coumarin-3-yl-1,4-enedione intermediate 5a. Further reduction
of 5a with stannous chloride afforded 1,4-diketone intermediate
c, which was finally converted into a furan derivate 6a via
Paal–Knorr cyclisation reactions.
Experimental
3-Acetylcoumarins 3a–f were synthesised according to a literature
method.27 Other reagents were obtained from commercial suppliers and
used without further purification. TLC analysis was performed using
pre-coated glass plates. Column chromatography was performed using
silica gel (200–300 mesh). NMR spectra were measured on a VXR 300
instrument. Chemical shifts are reported in ppm, relative to the internal
standard of tetramethylsilane (TMS). IR spectra were obtained as KBr
pellet samples on a Nicolet 5700 FTIR spectrometer. Mass spectra were
measured on a LCQ Advantage MAX (ESI). The elemental analyses
were performed with a Vario EL-III instrument (Germany).
In conclusion, we have synthesised a series of novel
3-(4-benzoyl-5-phenylfuran-2-yl) coumarins 6a–f via
a
three-step reaction from readily available salicylic aldehydes,
ethyl 3-oxobutanoate and 1,3-diphenylpropane-1,3-dione.
Fig. 1 ORTEP diagram of 6a with 30% probability.
O
O
O
O
O
I
DMSO
CHO
CuO, I2
HI
O
O
O
O
S
+
HI
A
B
3a
Ph Ph
O
O
O
O
Ph
Ph
O
O
O
O
Ph
Ph
Ph
O
O
SnCl2
AcOH
4
HCl
Ph
O
O
H2O
O
O
O
H2O
O
c
5a
6a
Scheme 2 Proposed reaction mechanism.

510 JOURNAL OF CHEMICAL RESEARCH 2018
Synthesis of compounds 5a–f; general procedure
was added, followed by compound 4 (0.5 mmol) in acetic acid (5 mL).
Heating was continued for 30 min then the reaction mixture was
poured into water (50 mL) and extracted with CH2Cl2 (3 ×15 mL). The
organic layer was washed with saturated NaHCO3 solution, and then
dried over anhydrous Na2SO4. The solvent was evaporated and the
residue was purified by column chromatography over silica gel with
petroleum ether/ethyl acetate (v/v, 18:1) to give product 6.
3-(4-Benzoyl-5-phenylfuran-2-yl)chromen-2-one (6a): Yellow solid;
yield 78%; m.p. 198–199 °C; IR (KBr) (νmax, cm−1): 3437, 1627, 1514,
823, 740; 1H NMR (300 MHz, CDCl3): δ 8.25 (s, 1H), 7.91–7.93 (d, 2H,
J = 7.5 Hz), 7.85–7.86 (m, 2H), 7.61–7.65 (m, 2H), 7.52–7.59 (m, 2H),
7.44–7.47 (m, 3H), 7.34–7.42 (m, 4H); 13C NMR (75 MHz, CDCl3): δ
191.3, 157.9, 155.9, 152.8, 146.0, 137.8, 134.7, 133.1, 131.6, 130.1, 129.8,
129.6, 129.3, 128.5, 128.1, 127.5, 124.9, 123.3, 119.1, 117.2, 116.6, 116.3;
MS (ESI) m/z: 807.00 [2M + Na]+. Anal. calcd for C26H16O4: C, 79.58;
H, 4.11; found: C, 79.54; H, 4.06%.
A mixture of 3-acetylcoumarins (3) (5.0 mmol), 1,3-diphenylpropane-
1,3-dione 4 (1.12 g, 5.0 mmol), iodine (1.40 g, 5.5 mmol) and CuO
(0.44 g, 5.5 mmol) in DMSO (20 mL) was heated at 70 °C for 12 h.
After filtration, the reaction mixture was then poured into brine
(100 mL) and the aqueous layer was extracted with CHCl3 (4 × 20 mL).
The extract was washed with 10% Na2S2O3, dried over anhydrous
Na2SO4 and concentrated in vacuo. The residue was purified by
column chromatography over silica gel with petroleum ether/ethyl
acetate (v/v, 20:1) as the eluent to give product 5.
2-Benzoyl-4-(2-oxo-2H-chromen-3-yl)-1-phenylbut-2-ene-1,4-
dione (5a): Yellow solid; yield 78%; m.p. 107–110 °C; IR (KBr) (νmax
,
cm−1): 3440, 1639, 1446, 680; 1H NMR (300 MHz, CDCl3): δ 8.45 (s,
1H), 8.07–8.09 (m, 2H), 8.01–8.04 (m, 2H), 7.84 (s, 1H), 7.44–7.68 (m,
8H), 7.34–7.38 (m, 2H); 13C NMR (75 MHz, CDCl3): δ 194.0, 192.9,
186.1, 159.1, 155.5, 151.2, 149.7, 135.5, 135.2, 134.0, 133.7, 133.3, 130.5,
130.3, 129.2, 128.8, 128.7, 127.2, 125.3, 123.5, 118.2, 116.8; MS (ESI)
m/z: 408.07 [M]+. Anal. calcd for C26H16O5: C, 76.46; H, 3.95; found:
C, 76.41; H, 3.92%.
3-(4-Benzoyl-5-phenylfuran-2-yl)-6-methylchromen-2-one
(6b):
Yellow solid; yield 74%; m.p. 182–183 °C; IR (KBr) (νmax, cm−1): 3431,
1
1629, 1508, 1398, 684; H NMR (300 MHz, CDCl3): δ 8.19 (s, 1H),
7.89–7.92 (m, 2H), 7.84–7.87 (m, 2H), 7.53–7.59 (m, 2H), 7.43–7.46 (m,
2H), 7.36–7.43 (m, 4H), 7.32 (s, 2H), 2.43(s, 3H, CH3–H); 13C NMR (75
MHz, CDCl3): δ 191.4, 158.1, 155.8, 151.0, 146.1, 137.8, 134.7, 134.5,
133.1, 132.7, 129.7, 129.5, 129.3, 129.1, 128.5, 127.9, 127.5, 123.3, 118.9,
117.0, 116.3, 116.1, 20.8; MS (ESI) m/z: 834.94 [2M + Na]+. Anal. calcd
for C27H18O4: C, 79.79; H, 4.46; found: C, 79.76; H, 4.43%.
3-(4-Benzoyl-5-phenylfuran-2-yl)-8-methoxychromen-2-one (6c):
Yellow solid; yield 76%; m.p. 178–179 °C; IR (KBr) (νmax, cm−1): 3438,
1628, 1566, 733; 1H NMR (300 MHz, CDCl3): δ 8.23 (s, 1H), 7.91 (d,
2H, J = 7.4 Hz), 7.85–7.87 (m, 2H), 7.63 (s, 1H), 7.54–7.57 (m, 1H),
7.42–7.47 (m, 3H), 7.37–7.39 (m, 3H), 7.20–7.25 (m, 1H), 7.10 (d, 1H,
J = 7.0 Hz), 3.99 (s, 3H, OCH3–H); 13C NMR (75 MHz, CDCl3): δ
191.4, 157.4, 155.9, 147.0, 146.0, 142.4, 137.7, 134.9, 133.2, 129.8, 129.6,
128.9, 128.5, 127.5, 125.6, 124.7, 123.3, 119.8, 119.5, 117.4, 116.3, 113.4,
56.3; MS (ESI) m/z: 422.12 [M]+. Anal. calcd for C27H18O5: C, 76.77; H,
4.29; found: C, 76.73; H, 4.26%.
2-Benzoyl-4-(6-methyl-2-oxo-2H-chromen-3-yl)-1-phenylbut-2-
ene-1,4-dione (5b): Yellow solid; yield 79%; m.p. 115–116 °C; IR
1
(KBr) (νmax, cm−1): 3438, 1724, 1658, 1586, 1491, 813, 691; H NMR
(300 MHz, CDCl3): δ 8.40 (s, 1H), 8.02–8.09 (m, 4H), 7.85 (s, 1H),
7.62–7.64 (m, 1H), 7.50–7.57 (m, 6H), 7.30–7.37 (m, 2H), 2.41 (s, 3H);
13C NMR (75 MHz, CDCl3): δ 194.1, 192.9, 186.3, 159.4, 153.7, 151.1,
149.7, 136.5, 135.9, 135.6, 135.3, 134.0, 133.7, 133.4, 130.3, 130.0, 129.2,
128.8, 128.7, 123.3, 118.0, 116.6, 20.7; MS (ESI) m/z: 422.12 [M]+.
Anal. calcd for C27H18O5: C, 76.77; H, 4.29; found: C, 76.73; H, 4.26%.
2-Benzoyl-4-(8-methoxy-2-oxo-2H-chromen-3-yl)-1-phenylbut-
2-ene-1,4-dione (5c): Yellow solid; yield 74%; m.p. 132–133 °C; IR
1
(KBr) (νmax, cm−1): 3439, 1783, 1640, 1456, 689; H NMR (300 MHz,
CDCl3): δ 8.43 (s, 1H), 8.01–8.09 (m, 4H), 7.85 (s, 1H), 7.62–7.69 (m,
2H), 7.44–7.55 (m, 6H), 7.51–7.24 (m, 1H), 3.97 (s, 3H); 13C NMR (75
MHz, CDCl3): δ 194.0, 192.9, 186.2, 185.7, 158.7, 151.1, 149.9, 147.1,
145.1, 135.5, 134.9, 133.6, 130.3, 129.8, 129.1, 129.0, 128.7, 127.1, 125.1,
121.5, 118.7, 116.6, 56.3; MS (ESI) m/z: 438.11 [M]+. Anal. calcd for
C27H18O6: C, 73.97; H, 4.14; found: C, 73.93; H, 4.11%.
3-(4-Benzoyl-5-phenylfuran-2-yl)-6-chlorochromen-2-one
(6d):
Yellow solid; yield 77%; m.p. 176–178 °C; IR (KBr) (νmax, cm−1): 3439,
1
1628, 1602, 767; H NMR (300 MHz, CDCl3): δ 8.15 (s, 1H), 7.90 (d,
2-Benzoyl-4-(6-chloro-2-oxo-2H-chromen-3-yl)-1-phenylbut-2-
ene-1,4-dione (5d): Yellow solid; yield 76%; m.p. 172–173 °C; IR
2H, J = 7.2 Hz), 7.82–7.85 (m, 2H), 7.62–7.64 (m, 2H), 7.54–7.56 (d,
1H, J = 7.5 Hz), 7.44–7.50 (m, 2H), 7.37–7.46 (m, 4H), 7.30–7.33 (d, 1H,
J = 8.6 Hz); 13C NMR (75 MHz, CDCl3): δ 191.2, 157.3, 156.3, 151.1,
145.6, 137.7, 133.2, 133.0, 132.9, 131.4, 130.2, 129.8, 129.2, 128.5, 127.6,
127.2, 123.5, 120.3, 118.3, 118.0, 117.1, 117.0. MS (ESI) m/z: 426.07 [M]+.
Anal. calcd for C26H15ClO4: C, 73.16; H, 3.54; found: C, 73.12; H, 3.51%.
1
(KBr) (νmax, cm−1): 3435, 1731, 1650, 1553, 1445, 686, 725; H NMR
(300 MHz, CDCl3): δ 8.35 (s, 1H), 8.01–8.09 (m, 4H), 7.77–7.79 (m,
2H), 7.72–7.74 (m, 2H), 7.48–7.63 (m, 6H); 13C NMR (75 MHz,
CDCl3): δ 193.8, 192.6, 185.8, 158.5, 153.7, 151.7, 148.1, 135.7, 135.4,
134.9, 134.0, 133.7, 132.8, 130.6, 130.3, 129.2, 129.1, 128.7, 127.5,
124.4, 119.1, 118.3; MS (ESI) m/z: 442.06 [M]+. Anal. calcd for
C26H15ClO5: C, 70.52; H, 3.41; found: C, 70.48; H, 3.38%.
3-(4-Benzoyl-5-phenylfuran-2-yl)-6-bromochromen-2-one
(6e):
Yellow solid; yield 76%; m.p. 156–157 °C; IR (KBr) (νmax, cm−1): 3438,
1629, 1575, 1398, 1107, 759, 676; 1H NMR (300 MHz, CDCl3): δ 8.11–8.16
(t, 2H), 7.91 (d, 2H, J = 7.2 Hz), 7.85–7.86 (m, 1H), 7.78–7.79 (m, 1H),
7.60–7.64 (m, 2H), 7.47–7.51 (m, 1H), 7.42–7.45 (m, 3H), 7.38–7.40 (m,
3H); 13C NMR (75 MHz, CDCl3): δ 191.3, 157.3, 156.3, 151.5, 145.5, 137.6,
134.2, 133.7, 133.2, 132.9, 130.2, 129.8, 129.1, 128.5, 128.47, 127.5, 123.4,
120.7, 118.3, 118.1, 117.5, 117.0; MS (ESI) m/z: 470.02 [M]+. Anal. calcd for
C26H15BrO4: C, 66.26; H, 3.21; found: C, 66.22; H, 3.18%.
2-Benzoyl-4-(6-bromo-2-oxo-2H-chromen-3-yl)-1-phenylbut-2-
ene-1,4-dione (5e): Yellow solid; yield 77%; m.p. 98–99 °C; IR (KBr)
1
(νmax, cm−1): 3438, 1640, 1774, 804, 687; H NMR (300 MHz, CDCl3):
δ 8.24 (s, 1H), 7.91–8.00 (m, 4H), 7.63–7.69 (m, 3H), 7.35–7.56 (m, 7H);
13C NMR (75 MHz, CDCl3): δ 193.8, 192.7, 185.8, 158.6, 154.2, 151.8,
148.0, 137.8, 135.8, 135.4, 134.1, 133.8, 132.8, 132.4, 130.3, 129.2, 128.8,
128.7, 124.4, 119.6, 118.6, 117.9. MS (ESI) m/z: 486.02 [M]+. Anal. calcd
for C26H15BrO5: C, 64.08; H, 3.10; found: C, 64.04; H, 3.07%.
3-(4-Benzoyl-5-phenylfuran-2-yl)-6-diethylaminochromen-2-
one (6f): Yellow solid; yield 71%; m.p. 198–199 °C; IR (KBr) (νmax
,
2-Benzoyl-4-(6-diethylamino-2-oxo-2H-chromen-3-yl)-1-phenylbut-
2-ene-1,4-dione (5f): Yellow solid; yield 78%; m.p. 121–122 °C; IR
(KBr) (νmax, cm−1): 3438, 1641, 1638, 1588, 1492, 723, 693; 1H NMR (300
MHz, CDCl3): δ 8.33 (s, 1H), 8.02–8.08 (m, 4H), 7.43–7.63 (m, 7H),
7.31–7.34 (m, 1H), 6.59–6.62 (m, 1H), 6.44 (s, 1H), 3.46 (q, 4H, J = 6.9
Hz), 1.24 (t, 6H, J = 6.8 Hz); 13C NMR (75 MHz, CDCl3): δ 194.7, 193.6,
185.6, 160.7, 159.1, 153.7, 149.5, 149.3, 136.2, 136.0, 135.2, 133.6, 133.3,
132.4, 130.2, 129.0, 128.6, 127.1, 114.7, 110.3, 108.7, 96.6, 45.3, 12.4. MS
(ESI) m/z: 480.12 [M + H]+. Anal. calcd for C30H25NO5: C, 75.14; H,
5.25; N, 2.92; found: C, 75.11; H, 5.21; N, 2.87 %.
cm−1): 3442, 1630, 1595, 1351, 764; H NMR (300 MHz, CDCl3): δ
8.12 (s, 1H), 7.91–7.94 (m, 2H), 7.84–7.87 (m, 2H), 7.52–7.57 (m, 1H),
7.38–7.47 (m, 4H), 7.33–7.38 (m, 3H), 6.64 (dd, 1H, J = 8.8, 2.4 Hz),
6.52–6.53 (m, 1H), 3.43 (q, 4H, J = 7.0 Hz), 1.23 (t, 6H, J = 7.1 Hz);
13C NMR (75 MHz, CDCl3): δ 191.7, 159.0, 155.8, 154.6, 150.8, 147.3,
138.1, 135.9, 132.9, 129.8, 129.2, 129.0, 128.6, 128.4, 127.3, 123.3,
113.3, 110.4, 109.4, 108.6, 97.2, 44.9, 12.5. MS (ESI) m/z: 949.08 [2M
+ Na]+. Anal. calcd for C30H25NO4: C, 77.74; H, 5.44; N, 3.02; found: C,
77.70; H, 5.41; N, 2.98.%.
1
Synthesis of compounds 6a–f; general procedure
X-ray diffraction study of compound 6a
A mixture of acetic acid (6 mL) and concentrated hydrochloric acid
(4 mL) was heated to boiling, and stannous chloride (1.13 g, 5 mmol)
A yellow crystal of the title compound 6a obtained by slow evaporation
from chloroform–methanol solution (20:1 v/v) was mounted on a glass

JOURNAL OF CHEMICAL RESEARCH 2018 511
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fibre in a random orientation at 296(2) K. The determination of the
unit cell and the data collection were performed with Mo Ká radiation
(λ = 0.71073 Å) on a Bruker Smart Apex-CCD diffractometer. The
structure was solved by direct methods with SHELXS-97 program and
expanded by Fourier technique. The non-hydrogen atoms were refined
anisotropically, and the hydrogen atoms were placed at the calculated
positions. Crystal data for 6a: C26H16O4, Mr = 392.39 g mol–1, monoclinic
space group P21/c, a = 10.153(6) Å, b = 10.549(6) Å, c = 18.999(9) Å,
α = 90°, β = 108.36(2) °, γ = 90°, V = 1931.3(18) Å3, T = 296.15 K, Z =
4, Dc = 1.350 g m–3, μ = 0.091 mm–1, F(000) = 816, Rint = 0.0251, 20764
reflections, 3543 with I > 2σ(I) for 271 parameters, GOF = 1.073, R1
= 0.0384, wR2 = 0.0991 [I > 2σ(I)] and R1 = 0.0445, wR2 = 0.1053 (all
data). CCDC 1504636 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge from The
Cambridge Crystallographic Data Centre via www. ccdc.cam.ac.uk/
data_request/cif.
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We thank Hubei Province Education Ministry Foundation of
China (Grant No. D20112507) and the Open Project Foundation
of Hubei Key Laboratory of Pollutant Analysis and Reuse
Technology (PA150209) for financial support.
Electronic Supplementary Information
The ESI associated with this paper can be found at:
http://ingentaconnect.com/content/stl/jcr/2018/00000042/00000010/art00004
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Received 10 August 2018; accepted 3 September 2018
Paper 1805576
https://doi.org/10.3184/174751918X15380427556768
Published online: 11 October 2018
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