Modified coumarins. 8. Synthesis of substituted 5-(4-methoxyphenyl)-7H-furo[3,2-g] chromen-7-ones

Article abstract of DOI:10.1023/A:1022626402415

The MacLeod method was used to synthesize a series of substituted 5-(4-methoxyphenyl)-7H-furo[3,2-g]chromen-7-ones, modified analogs of psoralen, from 7-hydroxy-4-(4-methoxyphenyl)coumarins.

Full text of DOI:10.1023/A:1022626402415

Chemistry of Natural Compounds, Vol. 38, No. 6, 2002
MODIFIED COUMARINS. 8. SYNTHESIS OF SUBSTITUTED
5-(4-METHOXYPHENYL)-7 -FURO[3,2- ]CHROMEN-7-ONES
H
g
M. M. Garazd,1 Ya. L. Garazd,2
A. S. Ogorodniichuk,1 and V. P. Khilya2
UDC 547.814.5
The MacLeod method was used to synthesize a series of substituted 5-(4-methoxyphenyl)-7H-furo[3,2-
g]chromen-7-ones, modified analogs of psoralen, from 7-hydroxy-4-(4-methoxyphenyl)coumarins.
Key words: coumarins, psoralen, neoflavones, 4-phenylcoumarins, furocoumarins, 5-(4-methoxyphenyl)-7 -furo[3,2-
H
]chromen-7-ones.
g
Derivatives of4-phenylcoumarin, which are known as neoflavones, are widelydistributed among plants, especiallythe
familiesClusiaceae(Guttiferae), Leguminosae, Rubiaceae, andThelypteridaceae. Morethan 130neoflavoneshavebeen isolated
from natural sources. Furanoracemosone (1) [1], disparfuran B (2) [2], disparacetylfuran A (3) [2], and isodisparfuran A (4)
[2], which are furocoumarins based on the 4-phenylcoumarin skeleton, were isolated from
and
Calophyllum
Mesua racemosa
, which belong to the Clusiaceae (Guttiferae) family.
dispar
Me
Me
Me
O
O
O
O
O
O
O
O
O
HO
O
O
O
O
Me
Me
Me
Me
Me
O
OH
O
O
OH
O
OH
1
2
3
4
Both natural and synthetic 4-phenylcoumarins possess wide spectra of biological activities. Neoflavones that are
isolatedfrom naturalrawmaterialexhibitantibactericidaland insecticidal [3, 4], antimalarial [5], sugar-reducing [6], antitumor
[7], andcytoxic[2]activities. TheyinhibitHIV-1reversetranscriptase[8]. Synthetic derivatives of4-phenylcoumarinstypically
have vasodilating [9], analeptic [10], antiatherosclerotic [11], and antibacterial [12, 13] activities.
Therefore, our goal was to modify the structures of 4-phenylcoumarins by fusing a furan ring to them to form
substituted 5-(4-methoxyphenyl)psoralens.
The key compounds 7-hydroxy-4-(4-methoxyphenyl)coumarin (5) and 7-hydroxy-8-methyl-4-(4-
methoxyphenyl)coumarin (6) were prepared in high yields by Pechmann condensation of ethyl-4-methoxybenzoylacetate with
resorcinol and 2-methylresorcinol, respectively, in the presence of conc. H SO as a condensing agent. We used a two-step
2
4
MacLeod method to form the furocoumarin ring. This enables the modification of the target furocoumarins on the furan and
coumarin fragments under mild conditions and in high yields without limitations.
1) Institute of Bioorganic and Petroleum Chemistry, National Academy of Sciences of the Ukraine, Kiev, ul.
Murmanskaya, 1, e-mail: gmm@i.com.ua; 2) Taras Shevchenko Kiev National University, Kiev, ul. Vladimirskaya, 64.
Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 428-436, November-December, 2002. Original article submitted
November 18, 2002.
0009-3130/02/3806-0539$27.00 ©2002 Plenum Publishing Corporation
539

R
R
R
R
O
O
O
O
O
O
O
O
O
O
O
O
Me
Me
Me Me
Me
R
1
R
1
OMe
OMe
OMe
OMe
35, 36
37 - 40
41 - 52
33, 34
1. 1N NaOH
1. 1N NaOH
1. 1N NaOH
1. 1N NaOH
+
+
+
2. H
2. H
+
2. H
2. H
R
R
R
R
O
O
O
O
O
Me
O
O
O
O
O
O
O
O
O
O
O
Me
R
Me
1
Me
Me
R
1
OMe
OMe
OMe
OMe
9, 10
11 - 14
7, 8
15 - 26
Me COCH Cl,
MeCOCH Cl,
2
R CO(Me)CHHal,
1
K CO
2 3
3
2
O
R
K CO
2
Hal
K CO
3
2
3
K CO
2
3
O
HO
O
R
1
O
OMe
O
Cl
5, 6
Br
R
MeO
K CO
2
K CO
2
3
3
O
O
K CO
2
3
Br
R
R
O
O
O
O
O
O
O
O
O
O
O
MeO
O
O
OMe
OMe
OMe
29, 30
27, 28
31, 32
1. 1N NaOH
1. 1N NaOH
1. 1N NaOH
+
2. H
+
+
2. H
2. H
R
R
R
O
O
O
O
O
O
O
O
O
O
MeO
OMe
OMe
OMe
57, 58
53, 54
55, 56
5,7, 9, 27, 29, 31, 33, 35, 53, 55, 57:
6, 8, 10, 28, 30, 32, 34, 36, 54, 56, 58:
R = H;
R = Me;
R = Me, R1 = Ph;
R = R1 = Me;
1, 37:
12, 38:
13, 39:
17, 43:
14, 40:
18, 44:
R = H, R1 = Me;
R = R1 = Me;
R = H, R1 = Ph;
R = H, R1 = Me;
15, 41:
19, 45:
23, 49:
16, 42:
R = R1 = H;
R = Me, R1 = H;
20, 46:
21, 47:
22, 48:
R = H, R1 = F;
R = H, R1 = Br;
R = Me, R1 = F;
24, 50:
R = H, R1 = Cl;
R = Me, R1 = Cl;
26, 52:
R = Me, R1 = OMe
25, 51:
R = Me, R1 = Br;
R = H, R1 = OMe;
540

The Williamson reaction of 5 and 6 with α-haloketones in the presence of potash leads in high yields (54-96%) to
substituted oxoethers 7-32. The alkylating agents in this reaction were chloroacetone (7, 8), 1-chloropinacolone (9, 10),
3-chloro-2-butanone (11, 12), 2-bromopropiophenone (13, 14), phenacylbromide (15, 16), 2-bromo-4′-methylacetophenone
(17, 18), 2-chloro-4′-fluoroacetophenone (19, 20), 2,4′-dichloroacetophenone (21, 22), 4-bromophenacylbromide (23, 24),
4-methoxyphenacylbromide (25, 26), 2-bromo-3′-methoxyacetophenone (27, 28), 1-(1-benzofuran-2-yl)-2-bromo-1-ethanone
(29, 30), and 2-chlorocyclohexanone (31, 32). PMR spectra of ketoethers 7-32 have signals for the 7-O-aklyl substitutents and
the 4-phenylcoumarin system. The IR spectra exhibit two bands in the range 1692-1733 cm-1, which are characteristic of C=O
stretches of the coumarin ring and the alkoxyl carbonyl [14]. The UV spectra of 7-32 contain three strong maxima at 202-211,
240-284, and 310-324 nm, which are typical of this type of compounds [14].
Solutions of ketones 7-32 in NaOH (1 N) were heated and acidified to cyclize smoothly and in high yields (74-95%)
to the corresponding substituted 5-(4-methoxyphenyl)-7H-furo[3,2-g]chromen-7-ones 33-58, synthetic analogs of psoralen
furocoumarins. The linear addition of the furan ring at the 6,7-position of the 4-phenylcoumarin was confirmed by PMR
spectroscopy. The PMR spectra of 33-58 exhibit a simplified splitting for the aromatic protons compared with the starting
ketones owing tothe lack of coupling toH-6 ofthe coumarin ring. For 9-methyl-5-(4-methoxyphenyl)-7H-furo[3,2-g]chromen-
7-ones, H-4 appears as a singlet at 7.21-7.71 ppm. In the spectra of furocoumarins that do not have a methyl in the 9-position,
H-4 and H-9 resonate as two singlets at 7.47-7.89 ppm. Furthermore, for 33-36 and 41-56, which are not substituted in the
2-position, a singlet is observed for H-2. This is also a characteristic feature of the formation of a furocoumarin ring. If an alkyl
substituent is present in the 3-position of 5-(4-methoxyphenyl)-7H-furo[3,2-g]chromen-7-one (33-36), the singlet ofH-2 occurs
at 7.70-7.87 ppm. Aryl substituents in the 3-position (41-56) shift the signal of H-2 to weaker field (8.31-8.50 ppm). The UV
spectra of the synthesized furocoumarins have absorption bands at 254-259 nm that are stronger than the longer wavelength
band (298-312 nm). This is also evidence of the addition of a furan ring to the 4-phenylcoumarin [14].
EXPERIMENTAL
The course ofreactions and purityofproducts were monitored byTLC on Merck 60 F254platesusing CHCl —CH OH
3
3
(9:1 and 95:5). IR and UV spectra were measured on Nicolet FTIR Nexus 475 and Specord M40 spectrophotometers,
respectively. PMRspectra were recorded on a Varian Mercury-400spectrometer relativetoTMS(internalstandard). Elemental
analyses of all compounds corresponded to those calculated.
7-Hydroxy-4-(4-methoxyphenyl)-2H-2-chromenone (5). A cooled (0 C) solution of resorcinol (22.0 g, 0.2 mole)
and ethyl-4-methoxybenzoylacetate (38.3 mL, 0.2 mole) in ethanol (50 mL) was vigorouslystirred, cooled, and treated dropwise
with conc. H SO (20 mL). The reaction mixture was stirred until thickened and left overnight at room temperature. The
2
4
mixture was poured into icewater (500 mL). The resulting precipitate was filtered off and crystallized from propan-2-ol. Yield
34.34 g (64%), C16H12O4, mp 265-266°C (lit. 260.5°C [15], 261-262°C [16]). IR spectrum (KBr, cm-1): 3199, 1705, 1622,
1608, 1511, 1443, 1382, 1273, 1254, 1230, 1186, 1122, 1037, 842, 828. UV spectrum (CH CN, λmax, nm, log ε): 203 (4.83),
3
311 (4.25). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 3.83 (3H, s, OMe-4′), 6.10 (1H, s, H-3), 6.77 (1H, dd, J = 2.4,
6
J = 9.2, H-6), 6.79 (1H, d, J = 2.4, H-8), 7.10 (2H, d, J = 8.4, H-3′, H-5′), 7.35 (1H, d, J = 9.2, H-5), 7.47 (2H, d, J = 8.4, H-2′,
H-6′), 10.63 (1H, br.s, OH-7).
7-Hydroxy-4-(4-methoxyphenyl)-8-methyl-2H-chromenone (6). Preparedanalogouslyto5from 2-methylresorcinol
(24.8 g, 0.2 mole) and ethyl-4-methoxybenzoylacetate (38.3 mL, 0.2 mole). Yield 42.91 g (76%), C17H14O4, mp 262-263°C.
IR spectrum (KBr, cm-1): 3222, 1698, 1604, 1575, 1562, 1517, 1506, 1371, 1325, 1312, 1300, 1265, 1244, 1180, 1092, 1027,
835, 820. UV spectrum (CH CN, λmax, nm, log ε): 204 (4.88), 310 (4.35). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz):
3
6
2.19 (3H, s, Me-8), 3.83 (3H, s, OMe-4′), 6.08 (1H, s, H-3), 6.83 (1H, d, J = 8.8, H-6), 7.10 (2H, d, J = 8.4, H-3′, H-5′), 7.19
(1H, d, J = 8.8, H-5), 7.44 (2H, d, J = 8.4, H-2′, H-6′), 10.49 (1H, br.s, OH-7).
4-(4-Methoxyphenyl)-7-(2-oxopropoxy)-2H-2-chromenone (7). A hot solution of 5 (1.07 g, 4 mmole) in absolute
acetone (30 mL) was treated with freshly calcined potash (1.66 g, 12 mmole), stirred vigorously and heated (50-56°C), and
treated with chloroacetone (0.35 mL, 4.4 mmole). The reaction mixture was left for 1 h with heating and vigorous stirring
(completion of the reaction determined by TLC). The reaction mixture was poured into H SO solution (300 mL, 1 N). The
2
4
resulting precipitate was filtered off and crystallized from propan-2-ol. Yield 1.01 g (78%), C19H16O5, mp 151-152°C. IR
spectrum (KBr, cm-1): 1733, 1715, 1608, 1517, 1419, 1377, 1305, 1281, 1267, 1249, 1185, 1150, 1116, 1067, 1029, 1005, 843.
541

UV spectrum (CH CN, λmax, nm, log ε): 203 (4.91), 313 (4.35). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 2.18 (3H,
3
6
s, CH -3″), 3.84 (3H, s, OMe-4′), 5.00 (2H, s, CH -1″), 6.19 (1H, s, H-3), 6.93 (1H, dd, J = 2.4, J = 9.2, H-6), 7.05 (1H, d,
3
2
J = 2.4, H-8), 7.12 (2H, d, J = 8.4, H-3′, H-5′), 7.42 (1H, d, J = 9.2, H-5), 7.49 (2H, d, J = 8.4, H-2′, H-6′).
4-(4-Methoxyphenyl)-8-methyl-7-(2-oxopropoxy)-2H-2-chromenone (8). Prepared analogously to 7 from 6
(1.13 g, 4 mmole) and chloroacetone (0.35 mL, 4.4 mmole). Yield 1.14 g (84%), C20H18O5, mp 181-182°C. IRspectrum (KBr,
cm-1): 1722, 1692, 1605, 1576, 1512, 1423, 1372, 1289, 1250, 1220, 1180, 1124, 1047, 1025, 820. UV spectrum (CH CN, λmax
,
3
nm, log ε): 203 (4.81), 310 (4.31). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 2.18 (3H, s, CH -3″), 2.28 (3H,
6
3
s, Me-8), 3.84 (3H, s, OMe-4′), 4.97 (2H, s, CH -1″), 6.18 (1H, s, H-3), 6.88 (1H, d, J = 9.2, H-6), 7.11 (2H, d, J = 8.4, H-3′,
2
H-5′), 7.27 (1H, d, J = 9.2, H-5), 7.44 (2H, d, J = 8.4, H-2′, H-6′).
7-(3,3-Dimethyl-2-oxobutoxy)-4-(4-methoxyphenyl)-2H-2-chromenone (9). Prepared analogously to 7 from 5
(1.07 g, 4 mmole) and 1-chloropinacolone (0.61 mL, 4.4 mmole). Yield 1.19 g (81%), C22H22O5, mp 140-141°C. IR spectrum
(KBr, cm-1): 1725, 1706, 1607, 1514, 1377, 1293, 1282, 1253, 1200, 1184, 1150, 1126, 1047, 1026, 1001, 982, 839, 826. UV
spectrum (CH CN, λmax, nm, log ε): 203 (4.91), 232 (4.49), 311 (4.39). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz):
3
6
1.20 [9H, s, (CH ) ], 3.85 (3H, s, OMe-4′), 5.22 (2H, s, CH -1″), 6.12 (1H, s, H-3), 6.85 (1H, dd, J = 2.4, J = 9.2, H-6), 6.98
3 3
2
(1H, d, J = 2.4, H-8), 7.09 (2H, d, J = 8.4, H-3′, H-5′), 7.41 (1H, d, J = 9.2, H-5), 7.44 (2H, d, J = 8.4, H-2′, H-6′).
7-(3,3-Dimethyl-2-oxobutoxy)-4-(4-methoxyphenyl)-8-methyl-2H-2-chromenone (10). Prepared analogously to 7
from 6 (1.13 g, 4 mmole) and 1-chloropinacolone (0.61 mL, 4.4 mmole). Yield 1.26 g (83%), C23H24O5, mp 161-162°C. IR
spectrum (KBr, cm-1): 1725, 1701, 1608, 1514, 1423, 1368, 1291, 1261, 1246, 1177, 1135, 1078, 997, 840, 812. UV spectrum
(CH CN, λmax, nm, log ε): 204 (4.76), 311 (4.28). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 1.18 [9H, s, (CH ) ],
3
6
3 3
2.28 (3H, s, Me-8), 3.83 (3H, s, OMe-4′), 5.31 (2H, s, CH -1″), 6.18 (1H, s, H-3), 6.81 (1H, d, J = 9.2, H-6), 7.11 (2H, d,
2
J = 8.4, H-3′, H-5′), 7.27 (1H, d, J = 9.2, H-5), 7.46 (2H, d, J = 8.4, H-2′, H-6′).
4-(4-Methoxyphenyl)-7-(1-methyl-2-oxopropoxy)-2H-2-chromenone (11). Prepared analogously to 7 from 5
(1.07 g, 4 mmole) and 3-chloro-2-butanone (0.44 mL, 4.4 mmole). Yield 0.92 g (68%), C20H18O5, mp 103-104°C. IR spectrum
(KBr, cm-1): 1725, 1606, 1513, 1421, 1375, 1305, 1268, 1251, 1201, 1184, 1151, 1118, 1089, 1033, 1005, 832. UV spectrum
(CH CN, λmax, nm, log ε): 203 (4.91), 313 (4.44). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 1.48 (1H, d, J = 7.2,
3
6
CH -1″), 2.21 (3H, s, CH -3″), 3.83 (3H, s, OMe-4′), 5.17 (1H, q, H-1″), 6.19 (1H, s, H-3), 6.92 (1H, dd, J = 2.4, J = 9.2, H-6),
3
3
6.99 (1H, d, J = 2.4, H-8), 7.11 (2H, d, J = 8.4, H-3′, H-5′), 7.42 (1H, d, J = 9.2, H-5), 7.48 (2H, d, J = 8.4, H-2′, H-6′).
4-(4-Methoxyphenyl)-8-methyl-7-(1-methyl-2-oxopropoxy)-2H-2-chromenone (12). Preparedanalogouslyto7from
6 (1.13 g, 4 mmole) and 3-chloro-2-butanone (0.44 mL, 4.4 mmole). Yield 1.04 g (74%), C21H20O5, mp 89-90°C. IR spectrum
(KBr, cm-1): 1721, 1602, 1513, 1426, 1370, 1278, 1255, 1180, 1127, 1110, 1019, 839. UV spectrum (CH CN, λmax, nm,
3
log ε): 204 (4.66), 311 (4.36). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 1.48 (1H, d, J = 7.2, CH -1″), 2.20 (3H,
6
3
s, CH -3″), 2.28 (3H, s, Me-8), 3.83 (3H, s, OMe-4′), 5.08 (1H, q, H-1″), 6.17 (1H, s, H-3), 6.84 (1H, d, J = 9.2, H-6), 7.09 (2H,
3
d, J = 8.4, H-3′, H-5′), 7.26 (1H, d, J = 9.2, H-5), 7.44 (2H, d, J = 8.4, H-2′, H-6′).
4-(4-Methoxyphenyl)-7-(1-methyl-2-oxo-2-phenylethoxy)-2H-2-chromenone (13). Preparedanalogouslyto7from
5 (1.07 g, 4 mmole) and 2-bromopropiophenone (0.66 mL, 4.4 mmole). The oil that formed after pouring the reaction mixture
into H SO (1 N) was extracted with ethylacetate (50 mL). The organic layer was successively washed with NaHCO solution
2
4
3
(5%, 25 mL), water (25 mL), H SO (1 N, 25 mL), water (25 mL), and saturated NaCl solution (25 mL). The organic layer
2
4
was dried over anhydrous MgSO . The solvent was removed in vacuum. The solid was ground with petroleum ether. The
4
mother liquor was poured off. The resulting oil was dried in vacuum. Yield 1.04 g (65%), C25H20O5, yellow oil. PMR
spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 1.61 (1H, d, J = 7.2, CH -1″), 3.82 (3H, s, OMe-4′), 6.17 (1H, s, H-3), 6.19 (1H,
6
3
q, H-1″), 6.92 (1H, dd, J = 2.4, J = 9.2, H-6), 6.99 (1H, d, J = 2.4, H-8), 7.11 (2H, d, J = 8.4, H-3′, H-5′), 7.40 (1H, d, J = 9.2,
H-5), 7.47 (2H, d, J = 8.4, H-2′, H-6′), 7.58 (2H, t, J = 7.6, H-3″′, H-5″′), 7.68 (1H, t, J = 7.6, H-4″′), 8.07 (2H, d, J = 7.6, H-2″,
H-6″′).
4-(4-Methoxyphenyl)-8-methyl-7-(1-methyl-2-oxo-2-phenylethoxy)-2H-2-chromenone (14). Preparedanalogously
to 7 from 6 (1.13 g, 4 mmole) and 2-bromopropiophenone (0.66 mL, 4.4 mmole). Yield 1.39 g (84%), C26H22O5, mp 140-
141°C. IR spectrum (KBr, cm-1): 1720, 1680, 1604, 1513, 1445, 1371, 1293, 1272, 1251, 1182, 1134, 1104, 1024, 837. UV
spectrum (CH CN, λmax, nm, log ε): 203 (4.90), 244 (4.37), 310 (4.31). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz):
3
6
1.60 (1H, d, J = 7.2, CH -1″), 2.29 (3H, s, Me-8), 3.81 (3H, s, OMe-4′), 6.17 (1H, s, H-3), 6.19 (1H, q, H-1″), 6.85 (1H, d,
3
J = 9.2, H-6), 7.06 (2H, d, J = 8.4, H-3′, H-5′),, 7.24 (1H, d, J = 9.2, H-5), 7.43 (2H, d, J = 8.4, H-2′, H-6′), 7.56 (2H, t, J = 7.6,
H-3″′, H-5″′), 7.69 (1H, t, J = 7.6, H-4″′), 8.06 (2H, d, J = 7.6, H-2″′, H-6″′).
542

4-(4-Methoxyphenyl)-7-(2-oxo-2-phenylethoxy)-2H-2-chromenone (15). Prepared analogously to 7 from 5
(1.07 g, 4 mmole) and phenacylbromide (0.84 g, 4.2 mmole). Yield 1.38 g (89%), C24H18O5, mp 192-193°C. IR spectrum
(KBr, cm-1): 1721, 1699, 1605, 1547, 1511, 1416, 1379, 1290, 1251, 1235, 1216, 1180, 1159, 1121, 1032, 1010, 978, 831. UV
spectrum (CH CN, λmax, nm, log ε): 202 (4.94), 240 (4.56), 313 (4.42). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz):
3
6
3.84 (3H, s, OMe-4′), 5.76 (1H, s, CH -1″), 6.19 (1H, s, H-3), 7.00 (1H, dd, J = 2.4, J = 9.2, H-6), 7.11 (2H, d, J = 8.4, H-3′,
2
H-5′), 7.17 (1H, d, J = 2.4, H-8), 7.43 (1H, d, J = 9.2, H-5), 7.49 (2H, d, J = 8.4, H-2′, H-6′), 7.58 (2H, t, J = 7.6, H-3″′, H-5″′),
7.71 (1H, t, J = 7.6, H-4″′), 8.04 (2H, d, J = 7.6, H-2″′, H-6″′).
4-(4-Methoxyphenyl)-8-methyl-7-(2-oxo-2-phenylethoxy)-2H-2-chromenone (16). Preparedanalogouslyto7from
6 (1.13 g, 4 mmole) and phenacylbromide (0.84 g, 4.2 mmole). Yield 1.49 g (93%), C25H20O5, mp 181-182°C. IR spectrum
(KBr, cm-1): 1721, 1699, 1608, 1513, 1425, 1370, 1294, 1262, 1246, 1231, 1179, 1132, 1025, 822. UV spectrum (CH CN, λmax
,
3
nm, log ε): 202 (4.96), 240 (4.47), 310 (4.36). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 2.33 (3H, s, Me-8), 3.82
6
(3H, s, OMe-4′), 5.77 (1H, s, CH -1″), 6.18 (1H, s, H-3), 6.98 (1H, d, J = 9.2, H-6), 7.09 (2H, d, J = 8.4, H-3′, H-5′), 7.26 (1H,
2
d, J = 9.2, H-5), 7.46 (2H, d, J = 8.4, H-2′, H-6′), 7.57 (2H, t, J = 7.6, H-3″′, H-5″′), 7.70 (1H, t, J = 7.6, H-4″′), 8.02 (2H, d,
J = 7.6, H-2″′, H-6″′).
4-(4-Methoxyphenyl)-7-[2-(4-methylphenyl)-2-oxoethoxy]-2H-2-chromenone (17). Preparedanalogouslyto7from
5 (1.07 g, 4 mmole) and 4-methylphenacylbromide (0.89 g, 4.2 mmole). Yield 1.44 g (90%), C25H20O5, mp 170-171°C. IR
spectrum (KBr, cm-1): 1713, 1700, 1609, 1514, 1422, 1378, 1289, 1262, 1245, 1221, 1184, 1165, 1121, 1027, 1011, 977, 812.
UV spectrum (CH CN, λmax, nm, log ε): 204 (4.93), 255 (4.42), 313 (4.35). PMR spectrum (400 MHz, DMSO-d , δ, ppm,
3
6
J/Hz): 2.40 (3H, s, Me-4″′), 3.84 (3H, s, OMe-4′), 5.72 (1H, s, CH -1″), 6.19 (1H, s, H-3), 7.00 (1H, dd, J = 2.4, J = 9.2, H-6),
2
7.11 (2H, d, J = 8.4, H-3′, H-5′), 7.15 (1H, d, J = 2.4, H-8), 7.39 (2H, d, J = 7.6, H-3″′, H-5″′), 7.43 (1H, d, J = 9.2, H-5), 7.49
(2H, d, J = 8.4, H-2′, H-6′), 7.94 (2H, d, J = 7.6, H-2″′, H-6″′).
4-(4-Methoxyphenyl)-8-methyl-7-[2-(4-methylphenyl)-2-oxoethoxy]-2H-2-chromenone (18). Preparedanalogously
to 7 from 6 (1.13 g, 4 mmole) and 4-methylphenacylbromide (0.89 g, 4.2 mmole). Yield 1.46 g (88%), C26H22O5, mp 207-
208°C. IRspectrum (KBr, cm-1): 1712, 1700, 1610, 1513, 1427, 1370, 1296, 1261, 1246, 1180, 1131, 1022, 811. UV spectrum
(CH CN, λmax, nm, log ε): 204 (4.91), 257 (4.40), 311 (4.34). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 2.33 (3H,
3
6
s, Me-8), 2.39 (3H, s, Me-4″′), 3.82 (3H, s, OMe-4′), 5.73 (1H, s, CH -1″), 6.19 (1H, s, H-3), 6.96 (1H, d, J = 9.2, H-6), 7.09
2
(2H, d, J = 8.4, H-3′, H-5′), 7.26 (1H, d, J = 9.2, H-5), 7.37 (2H, d, J = 8.0, H-3″′, H-5″′), 7.46 (2H, d, J = 8.4, H-2′, H-6′), 7.91
(2H, d, J = 8.0, H-2″′, H-6″′).
7-[2-(4-Fluorophenyl)-2-oxoethoxy]-4-(4-methoxyphenyl)-2H-2-chromenone (19). Preparedanalogouslyto7from
5 (1.07 g, 4 mmole) and 4-fluorophenacylchloride (0.72 g, 4.2 mmole). Yield 1.47 g (91%), C24H17FO5, mp 196-197°C. IR
spectrum (KBr, cm-1): 1712, 1695, 1600, 1510, 1416, 1378, 1290, 1252, 1234, 1217, 1181, 1157, 1121, 1032, 1011, 985, 837.
UV spectrum (CH CN, λmax, nm, log ε): 202 (4.97), 240 (4.47), 313 (4.36). PMR spectrum (400 MHz, DMSO-d , δ, ppm,
3
6
J/Hz): 3.84 (3H, s, OMe-4′), 5.74 (1H, s, CH -1″), 6.19 (1H, s, H-3), 6.99 (1H, dd, J = 2.4, J = 9.2, H-6), 7.11 (2H, d, J = 8.4,
2
H-3′, H-5′), 7.17 (1H, d, J = 2.4, H-8), 7.41 (2H, m, H-3″′, H-5″′), 7.44 (1H, d, J = 9.2, H-5), 7.49 (2H, d, J = 8.4, H-2′, H-6′),
8.12 (2H, m, H-2″′, H-6″′).
7-[2-(4-Fluorophenyl)-2-oxoethoxy]-4-(4-methoxyphenyl)-8-methyl-2H-2-chromenone (20). Preparedanalogously
to 7 from 6 (1.13 g, 4 mmole) and 4-fluorophenacylchloride (0.72 g, 4.2 mmole). Yield 1.56 g (93%), C25H19FO5, mp 199-
200°C. IR spectrum (KBr, cm-1): 1714, 1699, 1611, 1514, 1427, 1371, 1299, 1261, 1243, 1233, 1181, 1133, 1029, 835. UV
spectrum (CH CN, λmax, nm, log ε): 203 (4.84), 240 (4.37), 310 (4.27). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz):
3
6
2.33 (3H, s, Me-8), 3.83 (3H, s, OMe-4′), 5.75 (1H, s, CH -1″), 6.19 (1H, s, H-3), 6.98 (1H, d, J = 9.2, H-6), 7.09 (2H, d,
2
J = 8.4, H-3′, H-5′), 7.26 (1H, d, J = 9.2, H-5), 7.41 (2H, m, H-3″′, H-5″′), 7.46 (2H, d, J = 8.4, H-2′, H-6′), 8.10 (2H, m, H-2″′,
H-6″′).
7-[2-(4-Chlorophenyl)-2-oxoethoxy]-4-(4-methoxyphenyl)-2H-2-chromenone (21). Preparedanalogouslyto7from
5 (1.07 g, 4 mmole) and 4-chlorophenacylchloride (0.79 g, 4.2 mmole). Yield 1.45 g (86%), C24H17ClO5, mp 202-203°C. IR
spectrum (KBr, cm-1): 1710, 1694, 1617, 1514, 1419, 1383, 1293, 1252, 1220, 1181, 1162, 1125, 1088, 1036, 1010, 985, 826.
UV spectrum (CH CN, λmax, nm, log ε): 203 (4.67), 252 (4.41), 313 (4.38). PMR spectrum (400 MHz, DMSO-d , δ, ppm,
3
6
J/Hz): 3.84 (3H, s, OMe-4′), 5.75 (1H, s, CH -1″), 6.20 (1H, s, H-3), 7.01 (1H, dd, J = 2.4, J = 9.2, H-6), 7.11 (2H, d, J = 8.4,
2
H-3′, H-5′), 7.19 (1H, d, J = 2.4, H-8), 7.43 (1H, d, J = 9.2, H-5), 7.50 (2H, d, J = 8.4, H-2′, H-6′), 7.67 (2H, d, J = 8.4, H-3″′,
H-5″′), 8.05 (2H, d, J = 8.4, H-2″′, H-6″′).
7-[2-(4-Chlorophenyl)-2-oxooethoxy]-4-(4-methoxyphenyl)-8-methyl-2H-2-chromenone (22). Preparedanalogously
to 7 from 6 (1.13 g, 4 mmole) and 4-chlorophenacylchloride (0.79 g, 4.2 mmole). Yield 1.58 g (91%), C25H19ClO5, mp 206-
543

207°C. IR spectrum (KBr, cm-1): 1711, 1700, 1602, 1573, 1512, 1427, 1368, 1293, 1257, 1243, 1176, 1132, 1092, 1026, 983,
824. UV spectrum (CH CN, λmax, nm, log ε): 203 (4.62), 250 (4.13), 310 (4.03). PMR spectrum (400 MHz, DMSO-d , δ, ppm,
3
6
J/Hz): 2.31 (3H, s, Me-8), 3.82 (3H, s, OMe-4′), 5.75 (1H, s, CH -1″), 6.18 (1H, s, H-3), 6.98 (1H, d, J = 9.2, H-6), 7.09 (2H,
2
d, J = 8.4, H-3′, H-5′), 7.26 (1H, d, J = 9.2, H-5), 7.45 (2H, d, J = 8.4, H-2′, H-6′), 7.65 (2H, d, J = 8.0, H-3″′, H-5″′), 8.02 (2H,
d, J = 8.0, H-2″′, H-6″′).
7-[2-(4-Bromophenyl)-2-oxoethoxy]-4-(4-methoxyphenyl)-2H-2-chromenone (23). Preparedanalogouslyto7from
5 (1.07 g, 4 mmole) and 4-bromophenacylbromide (1.17 g, 4.2 mmole). Yield 1.75 g (94%), C24H17BrO5, mp 212-213°C. IR
spectrum (KBr, cm-1): 1716, 1696, 1615, 1587, 1513, 1419, 1382, 1292, 1251, 1219, 1179, 1162, 1125, 1035, 1010, 984, 829.
UV spectrum (CH CN, λmax, nm, log ε): 204 (4.93), 256 (4.47), 312 (4.34). PMR spectrum (400 MHz), DMSO-d , δ, ppm,
3
6
J/Hz): 3.84 (3H, s, OMe-4′), 5.74 (1H, s, CH -1″), 6.20 (1H, s, H-3), 7.01 (1H, dd, J = 2.4, J = 9.2, H-6), 7.11 (2H, d, J = 8.4,
2
H-3′, H-5′), 7.20 (1H, d, J = 2.4, H-8), 7.43 (1H, d, J = 9.2, H-5), 7.50 (2H, d, J = 8.4, H-2′, H-6′), 7.81 (2H, d, J = 8.0, H-3″′,
H-5″′), 7.97 (2H, d, J = 8.0, H-2″′, H-6″′).
7-[2-(4-Bromophenyl)-2-oxoethoxy]-4-(4-methoxyphenyl)-8-methyl-2H-2-chromenone (24). Preparedanalogously
to 7 from 6 (1.13 g, 4 mmole) and 4-bromophenacylbromide (1.17 g, 4.2 mmole). Yield 1.78 g (93%), C25H19BrO5, mp 224-
225°C. IR spectrum (KBr, cm-1): 1702, 1606, 1512, 1368, 1292, 1246, 1226, 1177, 1133, 1071, 982, 825. UV spectrum
(dioxane, λmax, nm, log ε): 211 (4.71), 257 (4.31), 302 (4.17). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 2.35 (3H,
6
s, Me-8), 3.84 (3H, s, OMe-4′), 5.68 (1H, s, CH -1″), 6.12 (1H, s, H-3), 6.90 (1H, d, J = 9.2, H-6), 7.06 (2H, d, J = 8.4, H-3′,
2
H-5′), 7.26 (1H, d, J = 9.2, H-5), 7.42 (2H, d, J = 8.4, H-2′, H-6′), 7.73 (2H, d, J = 8.0, H-3″′, H-5″′), 7.95 (2H, d, J = 8.0, H-2″′,
H-6″′).
4-(4-Methoxyphenyl)-7-[2-(4-methoxyphenyl)-2-oxoethoxy]-2H-2-chromenone (25). Preparedanalogouslyto7from
5 (1.07 g, 4 mmole) and 4-methoxyphenacylbromide (0.96 g, 4.2 mmole). Yield 1.58 g (95%), C25H20O6, mp 200-201°C. IR
spectrum (KBr, cm-1): 1731, 1715, 1680, 1603, 1512, 1382, 1319, 1291, 1269, 1243, 1171, 1156, 1121, 1031, 967, 825. UV
spectrum (CH CN, λmax, nm, log ε): 204 (4.94), 222 (4.65), 284 (4.55), 321 (4.35). PMR spectrum (400 MHz, DMSO-d , δ,
3
6
ppm, J/Hz): 3.84 (3H, s, OMe-4′), 3.87 (3H, s, OMe-4″′), 5.68 (1H, s, CH -1″), 6.19 (1H, s, H-3), 6.99 (1H, dd, J = 2.4, J = 2.4,
2
J = 8.4, H-6), 7.09 (2H, d, J = 9.2, H-3″′, H-5″′), 7.11 (2H, d, J = 9.2, H-3′, H-5′), 7.13 (1H, d, J = 2.4, H-8), 7.43 (1H, d,
J = 8.4, H-5), 7.49 (2H, d, J = 9.2, H-2′, H-6′), 8.02 (2H, d, J = 9.2, H-2″′, H-6″′).
4-(4-methoxyphenyl)-7-[2-(4-methoxyphenyl)-2-oxoethoxy]-8-methyl-2H-2-chromenone(26). Preparedanalogously
to 7 from 6 (1.13 g, 4 mmole) and 4-methoxyphenacylbromide (0.96 g, 4.2 mmole). Yield 1.53 g (89%), C26H22O6, mp 206-
207°C. IR spectrum (KBr, cm-1): 1716, 1698, 1600, 1557, 1514, 1423, 1369, 1293, 1261, 1240, 1177, 1134, 1025, 984, 836.
UV spectrum (CH CN, λmax, nm, log ε): 203 (4.95), 284 (4.61), 312 (4.45). PMR spectrum (400 MHz, DMSO-d , δ, ppm,
3
6
J/Hz): 2.32 (3H, s, Me-8), 3.83 (3H, s, OMe-4′), 3.85 (3H, s, OMe-4″′), 5.69 (1H, s, CH -1″), 6.18 (1H, s, H-3), 6.94 (1H, d,
2
J = 9.2, H-6), 7.07 (2H, d, J = 8.8, H-3″′, H-5″′), 7.09 (2H, d, J = 8.4, H-3′, H-5′), 7.26 (1H, d, J = 9.2, H-5), 7.46 (2H, d,
J = 8.4, H-2′, H-6′), 7.99 (2H, d, J = 8.8, H-2″′, H-6″′).
4-(4-Methoxyphenyl)-7-[2-(3-methoxyphenyl)-2-oxoethoxy]-2H-2-chromenone (27). Preparedanalogouslyto7from
5 (1.07 g, 4 mmole) and 3-methoxyphenacylbromide (0.96 g, 4.2 mmole). Yield 1.45 g (87%), C25H20O6, mp 202-203°C. IR
spectrum (KBr, cm-1): 1704, 1610, 1588, 1516, 1378, 1288, 1262, 1207, 1189, 1165, 1013, 989, 865. UV spectrum (CH CN,
3
λ
max, nm, log ε): 204 (4.83), 218 (4.69), 247 (4.28), 312 (4.35). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 3.84 (3H,
6
s, OMe-4′), 3.85 (3H, s, OMe-4″′), 5.76 (1H, s, CH -1″), 6.20 (1H, s, H-3), 7.01 (1H, dd, J = 2.4, J = 8.4, H-6), 7.12 (2H, d,
2
J = 9.2, H-3′, H-5′), 7.18 (1H, d, J = 2.4, H-8), 7.26 (1H, dd, J = 2.4, J = 8.4, H-4″′), 7.44 (1H, d, J = 8.4, H-5), 7.49 (2H, d,
J = 9.2, H-2′, H-6′), 7.52 (2H, m, H-2″′, H-5″′), 7.64 (1H, d, J = 7.6, H-6″′).
4-(4-Methoxyphenyl)-7-[2-(3-methoxyphenyl)-2-oxoethoxy]-8-methyl-2H-2-chromenone (28). Preparedanalogously
to 7 from 6 (1.13 g, 4 mmole) and 3-methoxyphenacylbromide (0.96 g, 4.2 mmole). Yield 1.65 g (96%), C26H22O6, mp 177-
178°C. IR spectrum (KBr, cm-1): 1700, 1609, 1586, 1514, 1426, 1371, 1299, 1261, 1206, 1181, 1127, 1054, 1023, 991, 827.
UV spectrum (CH CN, λmax, nm, log ε): 205 (4.76), 220 (4.66), 248 (4.18), 311 (4.31). PMR spectrum (400 MHz, DMSO-d ,
3
6
δ, ppm, J/Hz): 2.32 (3H, s, Me-8), 3.83 (6H, s, OMe-4′, OMe-4″′), 5.75 (1H, s, CH -1″), 6.18 (1H, s, H-3), 6.97 (1H, d, J = 9.2,
2
H-6), 7.09 (2H, d, J = 8.4, H-3′, H-5′), 7.27 (2H, m, H-5, H-4″′), 7.45 (2H, d, J = 8.4, H-2′, H-6′), 7.49 (2H, m, H-2″′, H-5″′),
7.60 (1H, d, J = 8.0, H-6″′).
7-(2-Benzo[b]furan-2-yl-2-oxoethoxy)-4-(4-methoxyphenyl)-2H-2-chromenone (29). Preparedanalogouslyto7from
5 (1.07 g, 4 mmole) and 1-(1-benzofuran-2-yl)-2-bromo-1-ethanol (1.00 g, 4.2 mmole). Yield 1.42 g (83%), C26H18O6, mp 191-
192°C. IR spectrum (KBr, cm-1): 1699, 1611, 1551, 1512, 1381, 1277, 1248, 1179, 1158, 1119, 1014, 995, 832. UV spectrum
544

(CH CN, λmax, nm, log ε): 202 (4.90), 236 (4.40), 302 (4.65). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 3.85 (3H,
3
6
s, OMe-4′), 5.69 (1H, s, CH -1″), 6.23 (1H, s, H-3), 7.06 (1H, dd, J = 2.4, J = 9.2, H-6), 7.13 (2H, d, J = 8.4, H-3′, H-5′), 7.23
2
(1H, d, J = 2.4, H-8), 7.42 (1H, t, J = 8.0, H-5″), 7.46 (1H, d, J = 9.2, H-5), 7.52 (2H, d, J = 8.4, H-2′, H-6′), 7.60 (1H, t, J = 8.0,
H-6″), 7.78 (1H, d, J = 8.0, H-7″), 7.92 (1H, d, J = 8.0, H-4″), 8.10 (1H, s, H-3″).
7-(2-Benzo[b]furan-2-yl-2-oxoethoxy)-4-(4-methoxyphenyl)-8-methyl-2H-2-chromenone (30). Preparedanalogously
to 7 from 6 (1.13 g, 4 mmole) and 1-benzo[b]furan-2-yl-2-bromo-1-ethanone (1.00 g, 4.2 mmole). Yield 1.60 g (91%),
C27H20O6, mp 182-183°C. IRspectrum (KBr, cm-1): 1711, 1694, 1609, 1557, 1513, 1427, 1370, 1288, 1248, 1179, 1127, 1062,
1014, 822. UV spectrum (CH CN, λmax, nm, log ε): 201 (4.81), 226 (4.43), 305 (4.55). PMR spectrum (400 MHz, DMSO-d ,
3
6
δ, ppm, J/Hz): 2.38 (3H, s, Me-8), 3.83 (3H, s, OMe-4′), 5.60 (1H, s, CH -1″), 6.12 (1H, s, H-3), 6.94 (1H, d, J = 9.2, H-6), 7.06
2
(1H, dd, J = 2.4, J = 9.2, H-6), 7.28 (1H, d, J = 9.2, H-6), 7.37 (1H, t, J = 8.0, H-5″), 7.42 (2H, d, J = 8.4, H-2′, H-6′), 7.55 (1H,
t, J = 8.0, H-6″), 7.68 (1H, d, J = 8.0, H-7″), 7.85 (1H, d, J = 8.0, H-4″), 8.00 (1H, s, H-3″).
4-(4-Methoxyphenyl)-7-(2-oxocyclohexyloxy)-2H-2-chromenone (31). A solution of5 (1.61 g, 6mmole)in absolute
DMF (30 mL) was treated with freshlycalcined potash (2.48 g, 18 mmole), stirred vigorouslyand heated (70-80°C), and treated
with 2-chlorocyclohexanone (1.15 mL, 10 mmole). The reaction mixture was heated and vigorouslystirred for 24 h and poured
into H SO (300 mL, 1 N). The resulting precipitate was filtered off and crystallized from propan-2-ol. Yield 1.18 g (54%),
2
4
C22H20O5, mp 185-186°C. IR spectrum (KBr, cm-1): 2941, 1733, 1712, 1605, 1515, 1374, 1284, 1250, 1181, 1109, 1028, 841.
UV spectrum (EtOH, λmax, nm, log ε): 205 (4.47), 324 (4.12). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 1.62-2.68
6
(8H, m, CH -3″, CH -4″, CH -5″, CH -6″), 3.85 (3H, s, OMe-4′), 5.19 (1H, m, H-2″), 6.10 (1H, s, H-3), 6.83 (1H, dd, J = 2.4,
2
2
2
2
J = 9.2, H-6), 6.96 (1H, d, J = 2.4, H-8), 7.08 (2H, d, J = 8.4, H-3′, H-5′), 7.39 (1H, d, J = 9.2, H-5), 7.44 (2H, d, J = 8.4, H-2′,
H-6′).
4-(4-Methoxyphenyl)-8-methyl-7-(2-oxocyclohexyloxy)-2H-2-chromenone (32). Prepared analogously to 31 from
6 (1.69 g, 6 mmole) and 2-chlorocyclohexanone (1.15 mL, 10 mmole). Yield 1.39 g (61%), C23H22O5, mp 190-191°C. IR
spectrum (KBr, cm-1): 2942, 1730, 1710, 1600, 1561, 1512, 1370, 1283, 1250, 1177, 1123, 1105, 1029, 838. UV spectrum
(EtOH, λmax, nm, log ε): 205 (4.71), 318 (4.22). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 1.65-2.60 (8H, m,
6
CH -3″, CH -4″, CH -5″, CH -6″), 2.29 (3H, s, Me-8), 3.84 (3H, s, OMe-4′), 5.14 (1H, m, H-2″), 6.10 (1H, s, H-3), 6.77 (1H,
2
2
2
2
d, J = 9.2, H-6), 7.07 (2H, d, J = 8.4, H-3′, H-5′), 7.22 (1H, d, J = 9.2, H-5), 7.41 (2H, d, J = 8.4, H-2′, H-6′).
5-(4-Methoxyphenyl)-7H-furo[3,2-g]chromen-7-ones 33-58. A solution or suspension of ketone 7-32 (2 mmole) in
propan-2-ol (10 mL) was treated with NaOH solution (10 mL, 1 N). The reaction mixture was heated for 4 h until the ketone
dissolved completely. The course of the reaction was monitored by TLC, after which H SO (20 mL, 1 N) was added. The
2
4
resulting precipitate was filtered off and crystallized from propan-2-ol.
5-(4-Methoxyphenyl)-3-methyl-7H-furo[3,2-g]chromen-7-one (33). Yield0.50g(82%), C19H14O4, mp200-201°C.
IR spectrum (KBr, cm-1): 1720, 1609, 1514, 1372, 1341, 1258, 1243, 1188, 1136, 1062, 1036, 830. UV spectrum (dioxane,
λ
max, nm, log ε): 213 (4.42), 238 (4.39), 254 (4.33), 298 (4.14). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 2.14 (3H,
6
s, Me-3), 3.86 (3H, s, OMe-4′), 6.29 (1H, s, H-6), 7.14 (2H, d, J = 8.4, H-3′, H-5′), 7.55 (2H, d, J = 8.4, H-2′, H-6′), 7.60 (1H,
s, H-9), 7.71 (1H, s, H-4), 7.86 (1H, s, H-2).
5-(4-Methoxyphenyl)-3,9-dimethyl-7H-furo[3,2-g]chromen-7-one (34). Yield 0.51 g (80%), C20H16O4, mp 178-
179°C. IR spectrum (KBr, cm-1): 1719, 1608, 1589, 1513, 1389, 1289, 1240, 1181, 1111, 1027, 849. UV spectrum (CH CN,
3
λ
max, nm, log ε): 204 (4.77), 271 (4.69), 232 (4.62), 253 (4.58), 302 (4.14). PMR spectrum (400 MHz, DMSO-d , δ, ppm,
6
J/Hz): 2.13 (3H, s, Me-3), 2.51 (3H, s, Me-9), 3.86 (3H, s, OMe-4′), 6.27 (1H, s, H-6), 7.14 (2H, d, J = 8.4 Hz, H-3′, H-5′), 7.44
(1H, s, H-4), 7.53 (2H, d, J = 8.4, H-2′, H-6′), 7.87 (1H, s, H-2).
3-(t-Butyl)-5-(4-methoxyphenyl)-7H-furo[3,2-g]chromen-7-one(35). Yield0.59g(85%), C22H20O4, mp193-194°C.
IR spectrum (KBr, cm-1): 1728, 1626, 1608, 1575, 1509, 1442, 1379, 1344, 1293, 1253, 1174, 1137, 1116, 1073, 1038, 835.
UV spectrum (CH CN, λmax, nm, log ε): 205 (4.73), 216 (4.64), 238 (4.55), 254 (4.45), 299 (4.34). PMR spectrum (400 MHz,
3
DMSO-d , δ, ppm, J/Hz): 1.33 [9H, s, (CH ) ], 3.89 (3H, s, OMe-4′), 6.26 (1H, s, H-6), 7.13 (2H, d, J = 8.4, H-3′, H-5′), 7.52
6
3 3
(2H, d, J = 8.4, H-2′, H-6′), 7.64 (1H, s, H-9), 7.71 (1H, s, H-4), 7.80 (1H, s, H-2).
3-(t-Butyl)-5-(4-methoxyphenyl)-9-methyl-7H-furo[3,2-g]chromen-7-one (36). Yield 0.62 g (86%), C23H22O4, mp
174-175°C. IR spectrum (KBr, cm-1): 1720, 1606, 1586, 1512, 1383, 1349, 1295, 1260, 1244, 1178, 1115, 1075, 1021, 841.
UV spectrum (CH CN, λmax, nm, log ε): 204 (4.72), 217 (4.66), 238 (4.53), 254 (4.48), 301 (4.33). PMR spectrum (400 MHz,
3
DMSO-d , δ, ppm, J/Hz): 1.31 [9H, s, (CH ) ], 2.55 (3H, s, Me-9), 3.89 (3H, s, OMe-4′), 6.23 (1H, s, H-6), 7.12 (2H, d,
6
3 3
J = 8.4, H-3′, H-5′), 7.48 (2H, d, J = 8.4, H-2′, H-6′), 7.63 (1H, s, H-4), 7.70 (1H, s, H-2).
545

5-(4-Methoxyphenyl)-2,3-dimethy-7H-furo[3,2-g]chromen-7-one (37). Yield 0.47 g (74%), C20H16O4, mp 208-
209°C. IR spectrum (KBr, cm-1): 1736, 1609, 1514, 1456, 1377, 1346, 1263, 1239, 1180, 1143, 1021, 829. UV spectrum
(CH CH, λmax, nm, log ε): 203 (4.70), 216 (4.60), 232 (4.53), 257 (4.51), 299 (4.28). PMR spectrum (400 MHz, DMSO-d ,
3
6
δ, ppm, J/Hz): 2.06 (3H, s, Me-3), 2.39 (3H, s, Me-2), 3.86 (3H, s, OMe-4′), 6.27 (1H, s, H-6), 7.14 (2H, d, J = 8.4, H-3′, H-5′),
7.47 (1H, s, H-9), 7.54 (2H, d, J = 8.4, H-2′, H-6′), 7.63 (1H, s, H-4).
5-(4-Methoxyphenyl)-2,3,9-trimethyl-7H-furo[3,2-g]chromen-7-one (38). Yield 0.54 g (81%), C21H18O4, mp 224-
225°C. IR spectrum (KBr, cm-1): 1734, 1609, 1586, 1515, 1399, 1378, 1263, 1179, 1155, 1101, 1022, 827. UV spectrum
(CH CN, λmax, nm, log ε): 218 (4.56), 233 (4.51), 257 (4.50), 302 (4.26). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz):
3
6
2.03 (3H, s, Me-3), 2.39 (3H, s, Me-2), 2.45 (3H, s, Me-9), 3.86 (3H, s, OMe-4′), 6.23 (1H, s, H-6), 7.13 (2H, d, J = 8.4, H-3′,
H-5′), 7.27 (1H, s, H-4), 7.50 (2H, d, J = 8.4, H-2′, H-6′).
5-(4-Methoxyphenyl)-2-methyl-3-phenyl-7H-furo[3,2-g]chromen-7-one (39). Yield 0.63 g (82%), C25H18O4, mp
223-224°C. IR spectrum (KBr, cm-1): 1726, 1608, 1568, 1513, 1437, 1376, 1340, 1262, 1177, 1143, 844. UV spectrum
(CH CN, λmax, nm, log ε): 223 (4.60), 258 (4.50), 302 (4.30). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 2.52 (3H,
3
6
s, Me-2), 3.83 (3H, s, OMe-4′), 6.27 (1H, s, H-6), 7.08 (2H, d, J = 8.4, H-3′, H-5′), 7.37 (1H, m, H-4″), 7.46 (4H, m, H-2″, H-3″,
H-5″, H-6″), 7.50 (2H, d, J = 8.4, H-2′, H-6′), 7.58 (1H, s, H-9), 7.72 (1H, s, H-4).
5-(4-Methoxyphenyl)-2,9-dimethyl-3-phenyl-7H-furo[3,2-g]chromen-7-one (40). Yield 0.68 g (86%), C26H20O4,
mp 246-247°C. IR spectrum (KBr, cm-1): 1726, 1606, 1585, 1513, 1393, 1375, 1336, 1297, 1264, 1177, 1120, 841. UV
spectrum (CH CN, λmax, nm, log ε): 222 (4.61), 258 (4.54), 304 (4.33). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz):
3
6
2.54 (6H, s, Me-2, Me-9), 3.82 (3H, s, OMe-4′), 6.28 (1H, s, H-6), 7.08 (2H, d, J = 8.4, H-3′, H-5′), 7.37 (1H, m, H-4″), 7.44
(1H, s, H-4), 7.46 (4H, m, H-2″, H-3″, H-5″, H-6″), 7.50 (2H, d, J = 8.4, H-2′, H-6′).
5-(4-Methoxyphenyl)-3-phenyl-7H-furo[3,2-g]chromen-7-one (41). Yield 0.63g(85%), C24H16O4, mp197-198°C.
IR spectrum (KBr, cm-1): 1728, 1628, 1607, 1563, 1512, 1438, 1374, 1342, 1300, 1247, 1194, 1185, 1164, 1137, 1073, 1030,
844. UV spectrum (CH CN, λmax, nm, log ε): 222 (4.66), 257 (4.44), 302 (4.32). PMRspectrum (400 MHz, DMSO-d , δ, ppm,
3
6
J/Hz): 3.84 (3H, s, OMe-4′), 6.33 (1H, s, H-6), 7.12 (2H, d, J = 8.4, H-3′, H-5′), 7.37 (1H, m, H-4″), 7.49 (2H, t, J = 7.6, H-3″,
H-5″), 7.58 (4H, d, J = 8.4, H-2′, H-6′, H-2″, H-6″), 7.86 (1H, s, H-9), 7.89 (1H, s, H-4), 8.43 (1H, s, H-2).
5-(4-Methoxyphenyl)-9-methyl-3-phenyl-7H-furo[3,2-g]chromen-7-one (42). Yield 0.67 g (88%), C25H18O4,
mp 235-236°C. IR spectrum (KBr, cm-1): 1723, 1606, 1585, 1512, 1380, 1295, 1261, 1247, 1177, 1117, 1094, 1024, 841. UV
spectrum (CH CN, λmax, nm, log ε): 222 (4.66), 257 (4.47), 304 (4.33). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz):
3
6
2.51 (3H, s, Me-9), 3.83 (3H, s, OMe-4′), 6.27 (1H, s, H-6), 7.08 (2H, d, J = 8.4, H-3′, H-5′), 7.35 (1H, m, H-4″), 7.43 (2H, t,
J = 7.6, H-3″, H-5″), 7.49 (2H, d, J = 9.2, H-2″, H-6″), 7.52 (2H, d, J = 8.4, H-2′, H-6′), 7.67 (1H, s, H-4), 8.40 (1H, s, H-2).
5-(4-Methoxyphenyl)-3-(4-methylphenyl)-7H-furo[3,2-g]chromen-7-one (43). Yield 0.60 g (79%), C25H18O4,
mp 201-202°C. IR spectrum (KBr, cm-1): 1708, 1626, 1606, 1582, 1511, 1444, 1376, 1345, 1293, 1252, 1179, 1162, 1137,
1072, 1024, 833. UV spectrum (CH CN, λmax, nm, log ε): 225 (4.69), 257 (4.48), 304 (4.36). PMR spectrum (400 MHz,
3
DMSO-d , δ, ppm, J/Hz): 2.31 (3H, s, Me-4″). 3.84 (3H, s, OMe-4′), 6.30 (1H, s, H-6), 7.11 (2H, d, J = 8.4, H-3′, H-5′), 7.24
6
(2H, d, J = 8.0, H-3″, H-5″), 7.43 (2H, d, J = 8.0, H-2″, H-6″), 7.53 (2H, d, J = 8.4, H-2′, H-6′), 7.79 (1H, s, H-9), 7.84 (1H, s,
H-4), 8.34 (1H, s, H-2).
5-(4-Methoxyphenyl)-9-methyl-3-(4-methylphenyl)-7H-furo[3,2-g]chromen-7-one (44). Yield 0.65 g (82%),
C26H20O4, mp 213-214°C. IRspectrum (KBr, cm-1): 1731, 1720, 1605, 1585, 1512, 1460, 1379, 1292, 1253, 1179, 1118, 1096,
1041, 1024, 838. UV spectrum (CH CN, λmax, nm, log ε): 224 (4.67), 237 (4.61), 255 (4.51), 305 (4.38). PMR spectrum
3
(400 MHz, DMSO-d , δ, ppm, J/Hz): 2.32 (3H, s, Me-4″), 2.53 (3H, s, Me-9), 3.85 (3H, s, OMe-4′), 6.28 (1H, s, H-6), 7.10 (2H,
6
d, J = 8.4, H-3′, H-5′), 7.24 (2H, d, J = 8.0, H-3″, H-5″), 7.41 (2H, d, J = 8.0, H-2″, H-6″), 7.52 (2H, d, J = 8.4, H-2′, H-6′), 7.67
(1H, s, H-4), 8.36 (1H, s, H-2).
3-(4-Fluorophenyl)-5-(4-methoxyphenyl)-7H-furo[3,2-g]chromen-7-one (45). Yield 0.64 g (83%), C24H15FO4,
mp 204-205°C. IR spectrum (KBr, cm-1): 1726, 1629, 1608, 1573, 1511, 1447, 1376, 1344, 1301, 1263, 1251, 1227, 1190,
1163, 1138, 1073, 1027, 832. UV spectrum (CH CN, λmax, nm, log ε): 224 (4.56), 257 (4.37), 302 (4.26). PMR spectrum (400
3
MHz, DMSO-d , δ, ppm, J/Hz): 3.85 (3H, s, OMe-4′), 6.35 (1H, s, H-6), 7.13 (2H, d, J = 8.4, H-3′, H-5′), 7.32 (2H, m, H-3″,
6
H-5″), 7.59 (2H, d, J = 8.4, H-2′, H-6′), 7.63 (2H, m, H-2″, H-6″), 7.86 (1H, s, H-9), 7.87 (1H, s, H-4), 8.43 (1H, s, H-2).
3-(4-Fluorophenyl)-5-(4-methoxyphenyl)-9-methyl-7H-furo[3,2-g]chromen-7-one (46). Yield 0.71 g (89%),
C25H17FO4, mp 258-259°C. IR spectrum (KBr, cm-1): 1721, 1604, 1585, 1511, 1381, 1259, 1245, 1224, 1184, 1119, 1097,
1020, 841. UV spectrum (CH CN, λmax, nm, log ε): 223 (4.47), 257 (4.43), 304 (4.18). PMR spectrum (400 MHz, DMSO-d ,
3
6
546

δ, ppm, J/Hz): 2.54 (3H, s, Me-9), 3.85 (3H, s, OMe-4′), 6.31 (1H, s, H-6), 7.11 (2H, d, J = 8.4, H-3′, H-5′), 7.31 (2H, m, H-3″,
H-5″), 7.53 (2H, d, J = 8.4, H-2′, H-6′), 7.58 (2H, m, H-2″, H-6″), 7.67 (1H, s, H-4), 8.42 (1H, s, H-2).
3-(4-Chlorophenyl)-5-(4-methoxyphenyl)-7H-furo[3,2-g]chromen-7-one (47). Yield 0.69 g (86%), C24H15ClO4,
mp 244-245°C. IR spectrum (KBr, cm-1): 1726, 1629, 1608, 1578, 1513, 1447, 1376, 1344, 1302, 1265, 1250, 1190, 1166,
1138, 1094, 1073, 1026, 831. UV spectrum (CH CN, λmax, nm, log ε): 222 (4.56), 240 (4.52), 257 (4.44), 302 (4.31). PMR
3
spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 3.87 (3H, s, OMe-4′), 6.30 (1H, s, H-6), 7.13 (2H, d, J = 8.4, H-3′, H-5′), 7.50
6
(2H, d, J = 8.0, H-3″, H-5″), 7.55 (2H, d, J = 8.4, H-2′, H-6′), 7.58 (2H, d, J = 8.0, H-2″, H-6″), 7.78 (1H, s, H-9), 7.85 (1H, s,
H-4), 8.38 (1H, s, H-2).
3-(4-Chlorophenyl)-5-(4-methoxyphenyl)-9-methyl-7H-furo[3,2-g]chromen-7-one (48). Yield 0.68 g (81%),
C25H17ClO4, mp 262-263°C. IR spectrum (KBr, cm-1): 1721, 1606, 1588, 1513, 1493, 1382, 1260, 1248, 1182, 1122, 1097,
1024, 832. UV spectrum (dioxane, λmax, nm, log ε): 223 (4.65), 242 (4.61), 258 (4.52), 302 (4.39). PMR spectrum (400 MHz,
DMSO-d , δ, ppm, J/Hz): 2.51 (3H, s, Me-9), 3.86 (3H, s, OMe-4′), 6.30 (1H, s, H-6), 7.10 (2H, d, J = 8.4, H-3′, H-5′), 7.49
6
(6H, m, H-2′, H-6′, H-2″, H-3″, H-5″, H-6″), 7.65 (1H, s, H-4), 8.40 (1H, s, H-2).
3-(4-Bromophenyl)-5-(4-methoxyphenyl)-7H-furo[3,2-g]chromen-7-one (49). Yield 0.81 g (91%), C24H15BrO4,
mp 243-244°C. IR spectrum (KBr, cm-1): 1726, 1608, 1576, 1513, 1376, 1344, 1301, 1265, 1249, 1189, 1165, 1137, 1078,
1025, 831. UV spectrum (CH CN, λmax, nm, log ε): 222 (4.58), 241 (4.55), 256 (4.48), 302 (4.32). PMR spectrum (400 MHz,
3
DMSO-d , δ, ppm, J/Hz): 3.87 (3H, s, OMe-4′), 6.34 (1H, s, H-6), 7.14 (2H, d, J = 8.4, H-3′, H-5′), 7.54 (2H, d, J = 8.0, H-3″,
6
H-5″), 7.58 (2H, d, J = 8.4, H-2′, H-6′), 7.66 (2H, d, J = 8.0, H-2″, H-6″), 7.86 (1H, s, H-9), 7.88 (1H, s, H-4), 8.46 (1H, s, H-2).
3-(4-Bromophenyl)-5-(4-methoxyphenyl)-9-methyl-7H-furo[3,2-g]chromen-7-one (50). Yield 0.88 g (95%),
C25H17BrO4, mp 267-268°C. IR spectrum (KBr, cm-1): 1722, 1606, 1513, 1382, 1260, 1248, 1182, 1123, 1098, 1078, 1024,
831. UV spectrum (CH CN, λmax, nm, log ε): 222 (4.78), 241 (4.69), 257 (4.64), 302 (4.47). PMR spectrum (400 MHz,
3
DMSO-d , δ, ppm, J/Hz): 2.56 (3H, s, Me-9), 3.86 (3H, s, OMe-4′), 6.33 (1H, s, H-6), 7.13 (2H, d, J = 8.4, H-3′, H-5′), 7.52
6
(2H, d, J = 8.0, H-3″, H-5″), 7.55 (2H, d, J = 8.4, H-2′, H-6′), 7.66 (2H, d, J = 8.0, H-2″, H-6″), 7.71 (1H, s, H-4), 8.50 (1H, s,
H-2).
3,5-Di(4-methoxyphenyl)-7H-furo[3,2-g]chromen-7-one (51). Yield 0.64 g (80%), C25H18O5, mp 202-203°C. IR
spectrum (KBr, cm-1): 1727, 1628, 1606, 1565, 1512, 1376, 1298, 1248, 1188, 1164, 1137, 1073, 1037, 1027, 835. UV
spectrum (CH CN, λmax, nm, log ε): 229 (4.78), 237 (4.76), 258 (4.64), 310 (4.52). PMR spectrum (400 MHz, DMSO-d , δ,
3
6
ppm, J/Hz): 3.79 (3H, s, OMe-4″), 3.86 (3H, s, OMe-4′), 6.34 (1H, s, H-6), 7.03 (2H, d, J = 8.4, H-3″, H-5″), 7.14 (2H, d,
J = 8.4, H-3′, H-5′), 7.52 (2H, d, J = 8.4, H-2″, H-6″), 7.59 (2H, d, J = 8.4, H-2′, H-6′), 7.85 (1H, s, H-9), 7.88 (1H, s, H-4), 8.34
(1H, s, H-2).
3,5-Di(4-methoxyphenyl)-9-methyl-7H-furo[3,2-g]chromen-7-one (52). Yield 0.73 g (88%), C26H20O5, mp 238-
239°C. IR spectrum (KBr, cm-1): 1723, 1607, 1585, 1512, 1460, 1381, 1296, 1255, 1230, 1179, 1116, 1025, 841. UV spectrum
(CH CN, λmax, nm, log ε): 228 (4.59), 240 (4.56), 259 (4.41), 311 (4.18). PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz):
3
6
2.53 (3H, s, Me-9), 3.78 (3H, s, OMe-4″), 3.86 (3H, s, OMe-4′), 6.28 (1H, s, H-6), 7.00 (2H, d, J = 8.4, H-3″, H-5″), 7.10 (2H,
d, J = 8.4, H-3′, H-5′), 7.45 (2H, d, J = 8.4, H-2″, H-6″), 7.51 (2H, d, J = 8.4, H-2′, H-6′), 7.66 (1H, s, H-4), 8.31 (1H, s, H-2).
3-(3-Methoxyphenyl)-5-(4-methoxyphenyl)-7H-furo[3,2-g]chromen-7-one (53). Yield0.68g(85%), C25H18O5, mp
187-188°C. IR spectrum (KBr, cm-1): 1729, 1609, 1568, 1515, 1428, 1377, 1348, 1257, 1224, 1187, 1139, 1071, 1050, 1023,
824. UV spectrum (CH CN, λmax, nm, log ε): 219 (4.82), 241 (4.61), 258 (4.51), 302 (4.45). PMR spectrum (400 MHz,
3
DMSO-d , δ, ppm, J/Hz): 3.76 (3H, s, OMe-3″), 3.84 (3H, s, OMe-4′), 6.34 (1H, s, H-6), 6.92 (1H, dd, J = 2.4, J = 8.4, H-4″′),
6
7.10 (2H, d, J = 8.4, H-3′, H-5′), 7.15 (2H, m, H-2″′, H-5″′), 7.36 (1H, m, H-6″′), 7.58 (2H, d, J = 8.4, H-2′, H-6′), 7.85 (1H,
s, H-9), 7.89 (1H, s, H-4), 8.46 (1H, s, H-2).
3-(3-Methoxyphenyl)-5-(4-methoxyphenyl)-9-methyl-7H-furo[3,2-g]chromen-7-one (54). Yield 0.67 g (81%),
C26H20O5, mp 183-184°C. IR spectrum (KBr, cm-1): 1733, 1721, 1607, 1588, 1513, 1382, 1294, 1262, 1243, 1214, 1185, 1119,
1021, 839. UV spectrum (CH CN, λmax, nm, log ε): 219 (4.68), 239 (4.52), 258 (4.38), 304 (4.34). PMR spectrum (400 MHz,
3
DMSO-d , δ, ppm, J/Hz): 2.52 (3H, s, Me-9), 3.75 (3H, s, OMe-3″), 3.84 (3H, s, OMe-4′), 6.29 (1H, s, H-6), 6.91 (1H, dd,
6
J = 2.4, J = 8.4, H-4″′), 7.09 (4H, m, H-3′, H-5′, H-2″, H-5″), 7.37 (1H, m, H-6″′), 7.52 (2H, d, J = 8.4, H-2′, H-6′), 7.69 (1H,
s, H-4), 8.44 (1H, s, H-2).
3-Benzo[b]furan-2-yl-5-(4-methoxyphenyl)-7H-furo[3,2-g]chromen-7-one(55). Yield0.60g(74%), C26H16O5, mp
259-260°C. IR spectrum (KBr, cm-1): 1720, 1608, 1512, 1453, 1376, 1346, 1296, 1259, 1177, 1157, 1136, 1070, 1027, 829.
UV spectrum (dioxane, λmax, nm, log ε): 212 (4.65), 221 (4.63), 245 (4.51), 267 (4.53), 274 (4.54), 314 (4.56), 322 (4.52). PMR
547

spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 3.91 (3H, s, OMe-4′), 6.39 (1H, s, H-6), 7.11 (1H, s, H-3″), 7.22 (2H, d, J = 8.4,
6
H-3′, H-5′), 7.28 (1H, t, J = 8.0, H-5″), 7.35 (1H, t, J = 8.0, H-6″), 7.50 (1H, d, J = 8.0, H-7″), 7.64 (2H, d, J = 8.4, H-2′, H-6′),
7.69 (1H, d, J = 8.0, H-4″), 7.93 (1H, s, H-9), 8.15 (1H, s, H-4), 8.75 (1H, s, H-2).
3-Benzo[b]furan-2-yl-5-(4-methoxyphenyl)-9-methyl-7H-furo[3,2-g]chromen-7-one (56). Yield 0.68 g (81%),
C27H18O5, mp 261-262°C. IR spectrum (KBr, cm-1): 1719, 1607, 1588, 1512, 1451, 1386, 1344, 1252, 1176, 1113, 1091, 1045,
840. UV spectrum (dioxane, λmax, nm, log ε): 218 (4.21), 242 (4.11), 259 (4.13), 267 (4.13), 312 (4.13), 334 (3.95). PMR
spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 2.61 (3H, s, Me-9), 3.92 (3H, s, OMe-4′), 6.30 (1H, s, H-6), 7.02 (1H, s, H-3″),
6
7.18 (2H, d, J = 8.4, H-3′, H-5′), 7.23 (1H, t, J = 8.0, H-5″), 7.30 (1H, t, J = 8.0, H-6″), 7.44 (1H, d, J = 8.0, H-7″), 7.57 (2H,
d, J = 8.4, H-2′, H-6′), 7.62 (1H, d, J = 8.0, H-4″), 7.99 (1H, s, H-4), 8.62 (1H, s, H-2).
4-(4-Methoxyphenyl)-6,7,8,9-tetrahydro-2H-benzo[4,5]furo[3,2-g]chromen-2-one (57). Yield 0.58 g (84%),
C22H18O4, mp 190-191°C. IR spectrum (KBr, cm-1): 2927, 1714, 1605, 1412, 1458, 1379, 1259, 1181, 1142, 1124, 1025, 837.
UV spectrum (EtOH, λmax, nm, log ε): 205 (4.68), 233 (4.53), 259 (4.59), 304 (4.37). PMR spectrum (400 MHz, DMSO-d ,
6
δ, ppm, J/Hz): 1.79 (2H, m, CH -7), 1.90 (2H, m, CH -8), 2.53 (2H, m, CH -6), 2.74 (2H, m, CH -9), 3.95 (3H, s, OMe-4′),
2
2
2
2
6.19 (1H, s, H-3), 6.27 (1H, s, H-3), 7.11 (2H, d, J = 8.4, H-3′, H-5′), 7.46 (2H, d, J = 8.4, H-2′, H-6′), 7.50 (1H, s, H-11), 7.55
(1H, s, H-5).
4-(4-Methoxyphenyl)-11-methyl-6,7,8,9-tetrahydro-2H-benzo[4,5]furo[3,2-g]chromen-2-one (58). Yield 0.62 g
(86%), C23H20O4, mp 222-223°C. IR spectrum (KBr, cm-1): 2945, 1720, 1606, 1583, 1513, 1458, 1398, 1341, 1256, 1178,
1132, 1114, 1091, 1020, 835. UV spectrum (EtOH, λmax, nm, log ε): 204 (4.64), 219 (4.54), 234 (4.44), 259 (4.43), 305 (4.21).
PMR spectrum (400 MHz, DMSO-d , δ, ppm, J/Hz): 1.78 (2H, m, CH -7), 1.91 (2H, m, CH -8), 2.50 (2H, m, CH -6), 2.53
6
2
2
2
(3H, s, CH -11), 2.75 (2H, m, CH -9), 3.94 (3H, s, OMe-4′), 6.19 (1H, s, H-3), 7.11 (2H, d, J = 8.4, H-3′, H-5′), 7.21 (1H, s,
3
2
H-5), 7.45 (2H, d, J = 8.4, H-2′, H-6′).
ACKNOWLEDGMENT
We thank OAO "Eximed" (the Ukraine, Kiev) for help with performing this work.
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