An efficient synthesis of new khellactone-type compounds using potassium hydroxide as catalyst via one-pot, three-component reaction

Article abstract of DOI:10.1007/s13738-013-0333-2

In the present work, three-component synthesis for novel khellactone-type compounds via the reaction of Meldrum's acid, aryl aldehydes and 5,7-dihydroxy benzopyrone derivatives was described. In this reaction 10-aryl substituted-9,10-dihydropyrano[2,3-h]benzopyrone-8-ones as new khellactone analogous in the presence of catalytic amount of potassium hydroxide as cheap and green basic catalyst were obtained in good to excellent yields under refluxing methanol.

Full text of DOI:10.1007/s13738-013-0333-2

J IRAN CHEM SOC (2014) 11:631–637
DOI 10.1007/s13738-013-0333-2
ORIGINAL PAPER
An efficient synthesis of new khellactone-type compounds
using potassium hydroxide as catalyst via one-pot,
three-component reaction
•
B. Karami K. Eskandari S. Khodabakhshi
•
Received: 3 March 2013 / Accepted: 25 August 2013 / Published online: 5 September 2013
Ó Iranian Chemical Society 2013
Abstract In the present work, three-component synthesis
for novel khellactone-type compounds via the reaction of
Meldrum’s acid, aryl aldehydes and 5,7-dihydroxy benzo-
pyrone derivatives was described. In this reaction 10-aryl
substituted-9,10-dihydropyrano[2,3-h]benzopyrone-8-ones
as new khellactone analogous in the presence of catalytic
amount of potassium hydroxide as cheap and green basic
catalyst were obtained in good to excellent yields under
refluxing methanol.
novel and complicated molecules. In addition, multicom-
ponent and multistep reactions have been designed to
produce biologically active compounds [1–5].
The core structures of d-lactones have been appeared as
a fragment in many natural products. These scaffolds can
exhibit a wide range of biological activities [6–8]. d-Lac-
tones are an important class of heterocyclic structures that
can be applied in drug and pharmaceutical fields [9–12].
These compounds have attracted scientific interest because
of their biological actions such as antimicrobial activity
through DNA gyrase-B [13], antioxidant activity against
superoxide and hydroxyl radicals, antimicrobial activity
against Escherichia coli and Staphylococcus aureus, anti-
biotic and cytotoxic activities, antiinflammatory, antiaging,
and anticancer activities [9–11]. Above all, heterocyclic
compounds containing oxygen as hetero atom which fused
with benzopyrone rings can act as novel anti-HIV agents
(khellactone-type compounds) [14–17]. For example, 30,40-
di-O-(S)-(-)-camphanoyl-(30R,40R)(?)-cis-khellactone (DCK)
and Suksdorfin (isolated from the fruit of Lomatium suk-
sdorfii) (Fig. 1), as pyran rings fused with a benzopyrone,
have been found to have anti-HIV activity [16, 17]. Some
khellactone-type compounds are also used for the preven-
tion of transmission of HIV infection from an HIV-infected
pregnant woman to a fetus [18].
Keywords Khellactone ꢀ Meldrum’s acid ꢀ
5,7-Dihydroxy benzopyrones ꢀ Aldehyde ꢀ
Condensation reaction
Introduction
In the last two decades, multicomponent reactions (MCRs)
have attracted much attention in the world of chemistry,
because of their convergence virtue, easy completion,
mainly high yields of products, high atom economy and
selectivity. MCRs are convergent reactions, in which three
or more substrates react together in one pot to produce
The manuscript has been presented at the ‘‘1st National Conference
on Multi-Component Reaction’’ in Institute of Science and High
Technology and Environmental sciences, Graduate University of
Advanced Technology, Kerman, Iran, 2012.
Benzopyrone derivatives mainly found in some plants
families such as Rutaceae and Umbelliferae. They exhibit a
broad range of biological activities including anticoagula-
tion, antifungal, anti-psoriasis, etc. [19].
Electronic supplementary material The online version of this
article (doi:10.1007/s13738-013-0333-2) contains supplementary
material, which is available to authorized users.
Reaction between malonic acid 1 and acetone 2 in the
presence of acetic anhydride and sulfuric acid led to the
formation of Meldrum’s acid as white crystals. From ele-
mental analysis data, in conjunction with acidic properties
of the Meldrum’s acid, firstly this product was formulated
as b-lactone of b-hydroxyisopropylmalonic acid 3 [20].
B. Karami (&) ꢀ K. Eskandari ꢀ S. Khodabakhshi
Department of Chemistry, Yasouj University, P.O. Box 353,
75918-74831 Yasouj, Iran
e-mail: karami@mail.yu.ac.ir
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synthesized. In continuation of our previous studies on the
development of various catalysts in the synthesis of organic
compounds [25–28], we used silica tungstic acid (STA),
which it is obtainable from the reaction of anhydrous sodium
tungstate with silica chloride (Scheme 2), as a powerful and
reusable catalyst for the solvent-free synthesis of substituted
benzopyrones 7 via the Pechmann condensation of phloro-
glucinol with b-ketoester (Scheme 3).
All synthesized benzopyrones were characterized by
NMR and IR spectral data and compared with authentic
samples [26].
In general, using a supported catalyst, in most cases, a
desired level of activity was achieved and the catalyst was
removed easily from the reaction mixture and reused. We
believed that the future of environmentally friendly catal-
ysis lies on supported catalysts. In this step, the reactions
proceeded under solvent-free conditions and the catalyst
was recycled for three times and reused with a little
appreciable loss in the catalytic activity.
Fig. 1 DCK and Suksdorfin as anti-HIV compounds
When more experimental data on the chemistry of this
product were collected, its correct structure was determined
to be 2,2-dimethyl-4,6-diketo-1,3-dioxane
(Scheme 1).
4
[21]
Meldrum’s acid can react with aryl aldehydes to produce
arylidene Meldrum’s acid as active intermediates [22–24].
In our study on the synthesis of heterocyclic compounds
[25–28], we report that three-component synthesis of d-
lactone derivatives-fused benzopyrone ring can be utilized
in biochemistry, pharmacology and medical applications.
For this purpose, after preparation of Meldrum’s acid
[20], some 7-hydroxybenzopyrone derivatives should be
After preparation of starting materials, finally, three-
component reaction as an our principal aim for the syn-
thesis of novel fused heterocyclic compounds was loaded
with Meldrum’s acid 4, 5,7-dihydroxy-4-substituted benz-
opyrone 7 and aromatic aldehyde 8 in the presence of KOH
as a cheap and eco-friendly catalyst under refluxing
methanol. This three-component reaction led to obtain
Scheme 1 Synthesis of
Meldrum’s acid
Scheme 2 Preparation of silica
tungstic acid
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J IRAN CHEM SOC (2014) 11:631–637
633
Scheme 3 STA-catalyzed
Pechmann condensation
Scheme 4 Synthesis of 10-aryl
substituted-9,10-dihydropyrano
[2,3-h]benzopyrone-8-ones
10-aryl
substituted-9,10-dihydropyrano[2,3-h]benzopy-
at 0 °C, acetone (40 mL) is added. After the addition of
acetone, the reaction mixture is stirred at room temperature
for 2 h. Then the reaction mixture is placed in a refrigerator
for 12 h to appear as crystalline product. Then the crystals
were filtrated and washed with cold water and recrystallized
from hot acetone to give the pure product 4.
rone-8-ones 9 (Scheme 4).
Experimental
General
General procedure for the synthesis of 5,7-dihydroxy-4-
substituted benzopyrones (compounds 7a, b)
Solvents were purified and dried by standard procedures
and distilled prior to use. Commercially available reagents
were purchased from Merck Chemical Co. Melting points
were measured on an electrothermal KSB1N apparatus. IR
spectra were recorded in the matrix of KBr with JASCO
FT-IR-680 plus spectrometer. 1H NMR and 13C NMR
spectra were recorded on a FT-NMR Bruker Avance Ultra
Shield Spectrometer at 400.13 and 100.62 MHz in DMSO-
d6 as solvent. Elemental analyses (C, H, N) were performed
with a Heraeus CHN–O-Rapid analyzer. The results agreed
favorably with the calculated values. TLC was performed
on TLC-grade silica gel-G/UV 254 nm plates.
b-Ketoester (1 mmol) was added to a mixture of phloro-
glucinol (1 mmol) and STA (0.25 g, 5 mol %) in a screw-
cap vial. The mixture was stirred in a preheated oil bath
(90 °C). After completion of the reaction, the solid product
was suspended in H2O (20 ml), filtered and recrystallized
from hot EtOH to give the pure product 7. Finally, the
catalyst was washed with EtOH, dried at 120 °C for 1 h,
and reused for the next run.
General procedure for the synthesis of 10-aryl
substituted-9,10-dihydropyrano[2,3-h]benzopyrone-8-
ones (Products 9a–h)
General procedure for the preparation of Meldrum’s
acid (compound 4)
For the preparation of these products, to a stirred solution
of the Meldrum’s acid (0.144 g) and aromatic aldehydes
(1 mmol) in 10 mL methanol, in the presence of basic
To a stirred mixture of malonic acid (52 g) and acetic anhy-
dride (60 mL) and catalytic amount of sulfuric acid (1.5 mL)
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3
2
catalytic amount of KOH (10 mol %), 5,7-dihydroxy-4-
methyl (or phenyl) benzopyrone (1 mmol) under reflux
condition was added. The reaction progress was controlled
by TLC (n-hexane/ethyl acetate, 1:1). After 0.5–2 h, the
reaction was completed and the residue was filtered. The
crude product recrystallized from ethanol to yield pure
product.
1H, CH), 3.31 (dd, J = 16.2 Hz, J = 8 Hz, 1H, CH),
3.81 (s, 3H, CH3) 4.82 (d, J = 7.2 Hz, 1H, CH), 6.05 (s,
1H, CH), 6.57 (s, 1H, CH), 6.74 (dd, 3J = 7.4 Hz,
4J = 1.6 Hz, 1H, aromatic CH), 6.81 (t, 1H, aromatic CH),
7.03 (d, J = 8 Hz, 1H, aromatic CH), 7.24 (m, 1H, aro-
matic CH), 11.09 (s, 1H, OH). 13CNMR (100.62 MHz,
DMSO-d6) d (ppm): 23.5, 30.3, 34.5, 55.0, 99.1, 102.6,
105.8, 111.2, 120.3, 127.4, 128.5, 128.7, 152.0, 154.2,
154.8, 156.4, 157.0, 159.0, 166.4. Anal. Calcd for
C20H16O6 (352.34): C, 68.18; H, 4.58. Found: C, 68.26; H,
4.62.
Representative spectral data
5-Hydroxy-4-methyl-10-phenyl-9,10-dihydropyrano[2,3-
h]benzopyrone-8-one (9a)
5-Hydroxy-4-methyl-10-(naphthalen-1-yl)-9,10-
dihydropyrano[2,3-h]benzopyrone-8-one (9d)
White solids, m.p: 333 °C (decomposed); yield 0.28 g,
88 %; IR (KBr) (mmax, cm-1): 3,255, 1,782, 1,694, 1,628,
1,605, 1,382. H NMR (400.13 MHz, DMSO-d6) d (ppm):
White solids, m.p: 350 °C (decomposed); yield 0.32 g,
88 %; IR (KBr) (mmax, cm-1): 3,226, 1,784, 1,678, 1,624,
1
1
2.51 (s, 3H, CH3), 2.95 (d, J = 16.0 Hz, 1H, CH), 3.38 (dd,
2J = 16.0 Hz, 3J = 7.2 Hz, 1H, CH), 4.73 (d, J = 6.0 Hz,
1H, CH), 6.09 (s, 1H, CH), 6.60 (s, 1H, CH), 7.11 (d,
J = 7.6 Hz, 2H, aromatic CH), 7.24 (t, J = 6.8 Hz, 1H,
aromatic CH), 7.32 (t, J = 7.2 Hz, 2H, aromatic CH),
11.15 (s, 1H, OH). 13CNMR (100.62 MHz, DMSO-d6) d
(ppm): 24.0, 34.3, 37.2, 99.9, 106.5, 111.7, 126.9, 127.6,
127.9, 129.4, 141.6, 152.5, 154.4, 155.5, 159.6, 167.2.
Anal. Calcd for C19H14O5 (322.31): C, 70.80; H, 4.38.
Found: C, 70.68; H, 4.55.
1,606, 1,388. H NMR (400.13 MHz, DMSO-d6) d (ppm):
2.59 (s, 3H, CH3), 2.90 (d, J = 15.6 Hz, 1H, CH), 3.52 (dd,
2J = 16.0 Hz, 3J = 7.2 Hz, 1H, CH), 5.60 (d, J = 6.8 Hz,
1H, CH), 6.06 (s, 1H, CH), 6.69 (s, 1H, CH), 6.74 (d,
J = 6.8 Hz, 1H, aromatic CH), 7.33 (t, J = 7.6 Hz, 1H,
aromatic CH), 7.63 (t, J = 7.6 Hz, 1H, aromatic CH), 7.71
(t, J = 7.6 Hz, 1H, aromatic CH), 7.85 (d, J = 8 Hz, 1H,
aromatic CH), 8.02 (d, J = 8 Hz, 1H, aromatic CH), 8.39
(d, J = 8.8 Hz, 1H, aromatic CH), 11.23 (s, 1H, OH).
13CNMR (100.62 MHz, DMSO-d6) d (ppm): 23.5, 30.4,
36.4, 99.4, 103.4, 106.1, 111.4, 122.9, 123.1, 125.4, 126.1,
126.8, 128.0, 129.0, 129.9, 133.8, 136.4, 151.9, 154.6,
154.8, 157.3, 158.9, 166.3. Anal. Calcd for C23H16O5
(372.37): C, 74.19; H, 4.33. Found: C, 74.19; H, 4.32.
5-Hydroxy-4-methyl-10-(2-chlorophenyl)-9,10-
dihydropyrano[2,3-h]benzopyrone-8-one (9b)
White solids, m.p: 328 °C (decomposed); yield 0.33 g,
92 %; IR (KBr) (mmax, cm-1): 3,219, 1,797, 1,680, 1,625,
5-Hydroxy-4-phenyl-10-phenyl-9,10-dihydropyrano[2,3-
1
1,605, 1,387. H NMR (400.13 MHz, DMSO-d6) d (ppm):
2.56 (s, 3H, CH3), 2.83 (dd, J = 16.0 Hz, J = 1.6 Hz,
h]benzopyrone-8-one (9e)
2
3
2
3
1H, CH), 3.47 (dd, J = 16 Hz, J = 7.2 Hz, 1H, CH),
5.05 (d, J = 6.4 Hz, 1H, CH), 6.08 (s, 1H, CH), 6.63 (s,
1H, CH), 6.70 (dd, 3J = 7.8 Hz, 4J = 1.2 Hz, 1H, aro-
matic CH), 7.22 (m, 1H, aromatic CH), 7.31 (m, 1H, aro-
Pale yellow solids, m.p: 276–277 °C; yield 0.32 g, 85 %; IR
(KBr) (mmax, cm-1): 3,330, 1,789, 1,732, 1,691, 1,624, 1,601,
1,437. 1H NMR (400.13 MHz, DMSO-d6) d (ppm): 2.99 (d,
J = 16.0 Hz, 1H, CH), 3.44 (m, 1H, CH), 4.81 (d,
J = 6.4 Hz, 1H, CH), 6.00(s, 1H, CH), 6.50(s, 1H, CH), 7.18
(d, J = 7.6 Hz, 2H, aromatic CH), 7.27 (t, J = 7.2 Hz, 1H,
aromatic CH), 7.33–7.40 (m, 7H, aromatic CH), 10.76 (s, 1H,
OH). 13CNMR (100.62 MHz, DMSO-d6) d (ppm): 34.4,
37.2, 100.0, 104.3, 105.0, 113.5, 127.0, 127.7, 127.8, 127.8,
128.5, 129.4, 139.4, 141.6, 152.7, 154.8, 156.0, 156.8, 159.4,
167.1. Anal. Calcd for C24H16O5 (384.38): C, 74.99; H, 4.20.
Found: C, 74.75; H, 4.36.
3
4
matic CH), 7.56 (q, J = 8.0 Hz, J = 1.2 Hz, aromatic
CH), 11.24 (s, 1H, OH). 13CNMR (100.62 MHz, DMSO-
d6) d (ppm): 23.5, 31.7, 35.0, 99.3, 102.2, 106.1, 111.5,
127.3, 127.9, 129.3, 130.2, 132.2, 137.7, 151.9, 154.3,
154.7, 157.5, 158.8, 166.0. Anal. Calcd for C19H13ClO5
(356.76): C, 63.97; H, 3.67. Found: C, 64.08; H, 3.75.
5-Hydroxy-4-methyl-10-(2-methoxyphenyl)-9,10-
dihydropyrano[2,3-h]benzopyrone-8-one (9c)
5-Hydroxy-4-phenyl-10-(2-chlorophenyl)-9,10-
White solids, m.p: 337 °C (decomposed); yield 0.31 g,
90 %; IR (KBr) (mmax, cm-1): 3,271, 1,778, 1,688, 1,628,
dihydropyrano[2,3-h]benzopyrone-8-one (9f)
1
1,605, 1,384. H NMR (400.13 MHz, DMSO-d6) d (ppm):
2.54 (s, 3H, CH3), 2.80 (dd, J = 15.2 Hz, J = 0.8 Hz,
Pale yellow solids, m.p: 298–300 °C; yield 0.37 g, 90 %;
IR (KBr) (mmax, cm-1): 3,353, 3,067, 1,778, 1,734, 1,692,
2
3
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635
1
1,621, 1,603, 1,434. H NMR (400.13 MHz, DMSO-d6) d
Results and discussion
(ppm): 2.88 (d, J = 15.6 Hz, 1H, CH), 3.51 (dd,
2J = 16.0 Hz, 3J = 7.6 Hz, 1H, CH), 5.14 (d, J = 6.8 Hz,
1H, CH), 5.99 (s, 1H, CH), 6.54 (s, 1H, CH), 6.79 (d,
J = 7.6 Hz, 1H, CH), 7.26 (t, J = 7.6 Hz, 1H, aromatic
CH), 7.32–7.41 (m, 6H, aromatic CH), 7.59 (d,
J = 7.6 Hz, 1H, aromatic CH), 10.86 (s, 1H, OH).
13CNMR (100.62 MHz, DMSO-d6) d (ppm): 32.2, 35.5,
99.9, 102.9, 105.1, 113.6, 127.8, 127.9, 128.5, 128.5,
129.8, 130.7, 132.7, 138.2, 139.3, 152.6, 155.3, 155.9,
157.2, 159.2, 166.5. Anal. Calcd for C24H15ClO5 (418.83):
C, 68.82; H, 3.61. Found: C, 68.76; H, 3.68.
It has been known that the presence of hydroxyl group on
the aromatic rings is a key factor for the activation of ring
in its ortho and para positions against electrophiles such as
arylidene Meldrum’s acid. Here, two hydroxyl groups on
the aromatic ring of benzopyrone activate this ring against
arylidene Meldrum’s acid (formed from condensation of
Meldrum’s acid with aldehydes) as a nucleophilic reagent.
By this achievement, several 4-aryl substituted dihyd-
ropyran-2-ones which are fused with benzopyrone ring
were obtained with excellent yields (Table 1).
1
The structures of compounds 9 were deduced from H
5-Hydroxy-4-phenyl-10-(2-methoxyphenyl)-9,10-
NMR, 13C NMR, FT-IR spectra and elemental analysis
data. The 1H NMR spectrum of 9h, for example, exhibited
a doublet at 2.97 ppm and a dd at 3.56 ppm for the two
diastereomeric hydrogens (CH2 group), a doublet at
5.70 ppm for benzylic CH group, a singlet at 5.99 ppm for
the olefinic proton, a singlet at 6.61 ppm for the aromatic
CH group, a doublet at 6.84 ppm for aromatic CH group, a
multiplet peak at 7.38 for six aromatic CH groups, a triplet
at 7.65 for aromatic CH group, a triplet at 7.74 for aromatic
CH group, a doublet at 7.88 for aromatic CH group, a
doublet at 8.04 for aromatic CH group, a doublet at 8.44 for
aromatic CH group, and a singlet at 10.86 for the OH
group. The 13C NMR spectrum of 9h showed signals for
methylene (31.07 ppm), benzylic carbon (36.98 ppm), sp2
carbons (100.03, 104.04, 105.22, 113.52, 123.60, 123.65,
126.04, 126.69, 127.43, 127.87, 127.92, 128.58, 129.60,
130.49, 134.40, 136.88, 139.47, 152.66, 155.66, 156.10,
157.05 ppm) and esteric carbonyls (159.34 and
166.87 ppm) in agreement with the proposed structure.
Also, FT-IR spectrum of 9h showed the absorption bands
at 3,337 cm-1 for hydroxyl group, 3,062 cm-1 for aro-
matic CH, 1,732 and 1,697 cm-1 for C=O groups, and at
1,240, 1,166 cm-1 for C–O groups which are consistent
with proposed structure for obtained product. It is believed
that current strategy could be applied for the synthesis of
various khellactone-type compounds in future. By this
achievement, the scope of heterocyclic compounds was
developed. Reaction strategy is facile, rapid and economic
which resulted to obtain desired products with high yields.
These types of compounds can be applied in medicine and
pharmacy, and can be considered by chemists in the future.
dihydropyrano[2,3-h]benzopyrone-8-one (9g)
Yellow solids, m.p: 288–290 °C; yield 0.35 g, 86 %; IR
(KBr) (mmax, cm-1): 3,310, 3,065, 2,839, 1,780, 1,733,
1,697, 1,623, 1,600, 1,493. 1H NMR (400.13 MHz,
DMSO-d6) d (ppm): 2.85 (d, J = 16.4 Hz, 1H, CH), 3.35
(dd, 2J = 16.4 Hz, 3J = 8.0 Hz, 1H, CH), 3.84 (s, 3H,
OCH3), 4.90 (d, J = 7.6 Hz, 1H, CH), 5.96 (s, 1H, CH),
6.48 (s, 1H, CH), 6.86 (d, J = 4.8 Hz, 2H, aromatic CH),
7.06 (d, J = 8.4 Hz, 1H, aromatic CH), 7.25–7.29 (m, 1H,
aromatic CH), 7.35–7.43 (m, 5H, aromatic CH), 10.71 (s,
1H, OH). 13CNMR (100.62 MHz, DMSO-d6) d (ppm):
31.0, 35.0, 55.5, 99.7, 103.2, 104.9, 111.8, 113.3, 120.9,
127.8, 127.8, 128.1, 128.4, 129.0, 129.2, 139.5, 152.8,
155.2, 156.0, 156.6, 157.0, 159.4, 166.9. Anal. Calcd for
C25H18O6 (414.41): C, 72.46; H, 4.38. Found: C, 72.33; H,
4.45.
5-Hydroxy-4-phenyl-10-(naphthalen-1-yl)-9,10-
dihydropyrano[2,3-h]benzopyrone-8-one (9h)
Orange solids, m.p: 285–286 °C; yield 0.36 g, 84 %; IR
(KBr) (mmax, cm-1): 3,337, 3,062, 1,732, 1,697, 1,622,
1,603, 1,437, 1,240, 1,166. 1H NMR (400.13 MHz,
DMSO-d6) d (ppm): 2.97 (d, J = 15.6 Hz, 1H, CH), 3.56
(dd, 2J = 16.0 Hz, 3J = 7.2 Hz, 1H, CH), 5.70 (d,
J = 6.8 Hz, 1H, CH), 5.99 (s, 1H, CH), 6.61 (s, 1H, CH),
6.84 (d, J = 7.2 Hz, 1H, aromatic CH), 7.36–7.41 (m, 6H,
aromatic CH), 7.65 (t, J = 7.6 Hz, 1H, aromatic CH), 7.74
(t, J = 7.2 Hz, 1H, aromatic CH), 7.88 (d, J = 8.0 Hz, 1H,
aromatic CH), 8.04 (d, J = 8.0 Hz, 1H, aromatic CH), 8.44
(d, J = 8.8 Hz, 1H, aromatic CH), 10.86 (s, 1H, OH).
13CNMR (100.62 MHz, DMSO-d6) d (ppm): 31.0, 36.9,
100.0, 104.0, 105.2, 113.5, 123.6, 123.6, 126.0, 126.6,
127.4, 127.8, 127.9, 128.5, 129.6, 130.4, 134.4, 136.8,
139.4, 152.6, 155.6, 156.1, 157.0, 159.3, 166.8. Anal.
Calcd for C28H18O5 (434.44): C, 77.41; H, 4.18. Found: C,
77.37; H, 4.23.
Conclusions
In summary, a new series of 10-aryl substituted-9,10-di-
hydropyrano[2,3-h]benzopyrone-8-ones has been synthe-
sized via an MCR approach and was characterized by
elemental and spectral analysis. This synthetic strategy
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J IRAN CHEM SOC (2014) 11:631–637
Table 1 Three-component
synthesis 10-aryl substituted-
9,10-dihydropyrano[2,3-
h]benzopyrone-8-ones
Product 9
Aldehyde
R
Yield (%)a M.p. (°C)
CH3
88
92
333 dec.
328 dec.
a
CH3
b
CH3
90
88
337 dec.
c
CH3
350 dec.
d
C6H5
85
276-277
e
C6H5
90
298-300
f
C6H5
86
288-290
g
C6H5
84
285-286
h
a Refers to isolated yields
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637
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allows forming the complicated oxygen containing fused
heterocyclic systems.
Acknowledgments Financial support from Yasouj University of
Iran is gratefully acknowledged.
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