Jalapathi Pochampalli et al.

/ Journal of Pharmacy Research 2012,5(4),1957-1962

Research Article Available online through
ISSN: 0974-6943 www.jpronline.info
Synthesis and characterization of some novel coumarin based
pyrazoles, isoxazole and pyrimidyl derivatives
Jalapathi Pochampalli*, DevenderMandalaa, b, Balanarsimha Doddi a , Umapathi Nallaa
a
Department of chemistry, PG College of Science, Osmania University, Hyderabad-500004, India.
b
Allied Fabrichem Pvt. Ltd, Plot No-185, Phase-II, IDA Mallapur, Hyderabad-500076, India.
Received on:17-01-2012; Revised on: 12-02-2012; Accepted on:10-04-2012

ABSTRACT
4-Hydroxy-7-methoxy-3-phenyl-chromen-2-one has been build-up in new methodology using 1-(2-hydroxy-4-methoxy-phenyl)-2-phenyl-ethanone in
presence of sodium in diethyl carbonate. 1, 3-diketone system has been developed at 8 th position of coumarin nucleus by Backer venkatraman rearrangement
reaction. It is furtherly converted into substituted pyrazoles, isoxazole and pyrimidines under appropriate conditions using ethanol as solvent. All
synthesized compounds were purified by column chromatography and structures are analyzed by FT-IR, 1 H-NMR, 13 C NMR and Mass spectrum.

Keywords: Diethyl carbonate; Hydroxy pyrimidines; Phenylaceticacid; Resorcinol; Pyrimedine.

INTRODUCTION:
Coumarin heterocyclics are one of the major classes of naturally occurring
compounds and constitute a family of pharmacetiutically active agents. A
number of coumarin derivatives endowed with a large number of biological
activities such as antihelmintics, hypnotic insecticidal anticoagulant and coro-
nary vasodilator.
Coumarin derivatives have been reported to serve as antibacterial [1-3], antioxi-
dant [4, 5], anti-inflammatory [6, 7] and antitumor [8, 9] agents. Some of the
coumarin have displayed CNS depressant and anti-HIV [10] activities. Isoxazole
derivatives are a promising structural moiety for drug designery, which are
reported to possess antibacterial, anticonvulsant [11], antipsychotic, anti-
inflammatory, antitumor [ 1 2 ], analgesic insecticidal, antioxidant [13] ,
antidepressant [14]and antimicrobial activities. Pyrazolone derivatives are well
known for their versatile pharmacological activities. These pharmacological
properties of Coumarin, Isoxazole and pyrazole aroused our interest in syn-
thesizing some novel Coumarin molecules containing pyrazole/isoxazole
nuclei within the same molecule with the aim of testing their biological activ-
ity.
MATERIALS & METHODS:
Thin Layer Chromatography (TLC) was performed on E.Merk All Silica gel
60 F254 plates are visualized under UV light. The infrared (IR) spectra were
determined in a perkin-Elmer Fourier transform (FDIR spectrum). 1 H-NMR
spectra were recorded on Varian EM-360 (400MHz mercury plus) spec-
trometer in DMSO-d6 or CDCl3 and calibrated using solvent signals
[7.25(CDCl3 ) and 2.50(DMSO-d6 )]. All chemical shifts recorded in d (ppm)
using TMS as an internal standard. The mass spectra were recorded on
Agilent ion trap MS. Spectrometer at energy of ionizing electron equal to
70ev.
RESULTS AND DISCUSSION:
1- [2, 4-Dihydroxy phenyl] phenylethanone [15, 16] (2) has been prepared by
heating of resorcinol and phenylaceticacid in the presence of BF3 etharate
which is served as lewis acid. This compound was methylated with
Iodomethane-K2 CO3 in acetone to obtain compound (3). This reaction is
chemo selective, it offered the product (3) as major and confirmed by 1 H-
NMR spectra, in which the broad singlet at 5.38 corresponds to normal
phenolic protan is disappeared and mass spectral data (m/z: 243) is also
supported. The compound (3) was allowed to react with sodium in
diethylcarbonate to yield corresponding substituted coumarin [17] (4). Disap-
pearance of benzylic protons and appearance of enolic protons in compound
(4) in 1 H-NMR spectra indicating that the formation coumarin ring. This
compound (4) is treated with HI-acetic acid in Ac2 O (5)followed by acety-
lated in pyridine-AC2 O to afford diacetylated product (6). In the next step
compound (6) is subjected to fries migration with AlCl3 at 160C to afford
two isomeric products [18]. These are separated by column chromatography
using silica gel (60-120 mesh). In our laboratory, for the past several years,
we have been working on development of pyrazole, isoxazole and thiazole
based heterocyclic molecules. In continuation of our program, aimed at devel-
oping pharmaceutically active agents, we wanted to build up different het-
erocyclic moieties at 8th position of coumarin nuclei, for this reason we have
chosen isomer (7) and this compound was again acetylated in pyridine-Ac2 O
(8) and then subjected to rearrangement reaction according to the Baker
venkatraman rearrangement procedure. The resulted 1,3-diketone (9) has
been treated with hydrazine hydrate , hydroxylamine hydrochloride , phenyl
hydrazine , 2,4-dinitro phenyl hydrazine, urea at appropriate temperature in
ethanol to offered corresponding pyrazole, isoxazole, N-phenyl pyrazole,
N-(2,4 dinitro) phenyl pyrazole, hydroxy pyrimidyl derivatives respectively.
All the products have been analyzed by the FT- IR, 1 H-NMR, 13 C NMR and
mass spectra.

*Corresponding author. Experimental procedures:

Jalapathi Pochampalli,
Dept. of Chemistry, Preparation of 1-(2, 4-Dihydroxy-phenyl)-2-phenyl-ethanone (2):
PG College of Science, Phenylaceticacid (1.35g, 9.99mmol) was added to a solution of resorcinol (1)
Osmania University, Saifabad-500004, (1.0g, 9.09mmol) in BF3 -etharate (10mL) at room temperature and this mix-
Hyderabad-500004, India ture was heated at 85C for 4h. The reaction mixture was allowing to room
temperature and quenched with saturated sodium acetate (25mL) solution

Journal of Pharmacy Research Vol.5 Issue 4.April 2012 1957-1962

 Jalapathi Pochampalli et al. / Journal of Pharmacy Research 2012,5(4),1957-1962
and extracted with ethyl acetate (3x50mL). The combined organic layers
successively washed with water, brine solution and dried over anhydrous
Na2 SO4 and evaporated under vacuum. The crude product was purified with
column chromatography using 60-120 silica mesh and the pure product elute
at 20% ethyl acetate in pet ether to afford 1.8g (86.9%) of 1-(2, 4-Dihydroxy-
phenyl)-2-phenyl-ethanone (2) as light brown color solid.
1
H-NMR-(400MHz) in CDCl3 : 12.64 (s, 1H); 7.76 (d, 1H); 7.36-7.28 (m,
5H); 6.38 (d, 2H); 5.38 (br, 1H); 4.23 (s, 2H); m/z: 229 (M+H) +; IR (KBr)
cm-1 : 3550 (-OH, br), 1680 (C=O), 1450 (CH=CH).
droxy-4-methoxy-phenyl)-2-phenyl-ethanone (3) (1.0g, 4.13mmol) in di-
ethyl carbonate (5mL, 5vol) at 0C over period of 10min. The mixture was
wormed to room temperature and stirred for overnight. The reaction mixture
quenched with sufficient methanol, diluted with ether and extracted with
water (2x50mL) and washed with diethyl ether (2x25mL), The aquies layer
acidified with 2N HCl and extracted with ethyl acetate (3x50mL) the com-
bined organic layers dried over Na2 SO4 and concentrated under vaccuo to
afford 650mg (59%) of 4-hydroxy-7-methoxy-3-phenyl-chromen-2-one (4)
as brown color solid.

HO OH HO OH
O OH
Phenyl acetic acid O O O
(a),87% (b),85% (c),59%
(1) O
O
(2) OH
(3) (4)

O
HO O O O O O
HO O O
(d),63% (e),95% O
(f),46% (g),78%
OH O
OH
(5) (7)
O (6)
O

O O

O O O HO O O

O (h),76%
O Scheme-1:
O

O (8) O (9)

Reagents for above Scheme: (a) BF3 -Etharate,80C (b) MeI/K2CO3-Acetone (c) Diethylcarbonate/Sodium metal (d) HI/AcOH-AC2 O
(e) Pyridine/AC2O (f) AlCl3,160C (g) Pyridine/AC2O (h) NaH-THF
Preparation of 1-(2-hydroxy-4-methoxy-phenyl)-2-phenyl-ethanone (3):
Potassium carbonate (725mg, 5.25mmol) and Iodomethane (0.28mL,
4.38mmol) was added to a solution of 1-(2, 4-Dihydroxy-phenyl)-2-phenyl-
ethanone (2) (1.0g, 4.38mmol) in acetone at room temperature. This solution
was heated at 65C for 2h, the mixture cool to room temperature, filtered,
and the volatiles were evaporated by rotary diluted in ethyl acetate (50mL)
and successively washed with water, brine solution to afford 900mg (84.9%)
of 1-(2-hydroxy-4-methoxy-phenyl)-2-phenyl-ethanone (3) as off white color
solid.
1
H-NMR-(400MHz) in CDCl3 : 12.64 (s, 1H); 7.76 (d, 1H); 7.36-7.28 (m,
5H); 6.38 (d, 2H); 4.23 (s, 2H); 3.82 (s, 3H): m/z: 243 (M+H) +; IR (KBr) cm-
1
: 3550 (-OH, br), 2933 (CH str. Of CH3 ), 1692 (C=O), 1450 (CH=CH).
Preparation of 4-hydroxy-7-methoxy-3-phenyl-chromen-2-one (4):
Sodium (380mg, 16.52mmol) was added slowly to a solution of 1-(2-hy-
1
H-NMR-(400MHz) in CDCl3 : 7.80 (d, 1H); 7.56-7.43 (m, 5H); 6.96 (d,
1H); 6.69 (s, 1H); 3.98 (s, 3H); 13 C-NMR in CDCl3 : 54.30, 102.34,
106.53, 109.98, 111.32, 126.02, 131.40, 131.40,135.55, 156.66, 159.80,
162.75; m/z: 269 (M+H) +; ESI-HRMS: m/z Calcd. For C16 H12 O4 [M+H]
+
269.1291; Found: 269.1295; IR (KBr) cm-1 : 3490 (-OH, br), 1725(C=O of
lactone ring), 1450 (CH=CH), 1156 (C-O-C).
Preparation of 4, 7-dihydroxy-3-phenyl-chromen-2-one (5):
A suspension of 7-methoxy-3-phenyl-chroman-2, 4-dione (4) (2.0g,
7.46mmol), Hydroiodic acid (2vol, 4mL) in acetic acid (10vol, 20mL) and
acetic anhydride (5vol, 10mL) was heated to 100C for 45min. The reaction
mixture allows to room temperature, volatiles were evaporated, diluted with
ethyl acetate (50mL) and washed with water (25mL) and brine (25mL)
solution. The organic layer was evaporated by rotary. The crude compound
was recrystalized from aq.ethanol to afford 1.2g of (63.4%) 4, 7-dihydroxy-
3-phenyl-chromen-2-one (5) as pale yellow color solid.

Journal of Pharmacy Research Vol.5 Issue 4.April 2012 1957-1962

 Jalapathi Pochampalli et al. / Journal of Pharmacy Research 2012,5(4),1957-1962

O
N

HO O O
O

O O
O (k), 68% O
N (11) N
O O (j), 67% O
N
N
HO HO O O
(12) HO O O

(l), 60% O (i), 73%

O
O
N O2 O
O 2N Compound-9 O
O (10)
N (m), 75%
N O
HO O N
O
(13) N

HO O O

Scheme-2:
O
(14)
O
R e a g e n t s f o r a b o v e S c h e m e: (i) H 2 N - N H 2 - H 2 O ( j ) N H 2 OH (k) Phenylhydrazine (l) 2, 4-DNP (m) Urea in Ethanol
1
H-NMR-(400MHz) in DMSO-d6 : 11.06 (s, 1H); 10.52 (s, 1H); 7.86 (d, brine solution. The crude compound was purified by column chromatogra-
1H); 7.42-7.31 (m, 5H); 6.80 (d, 1H); 6.72 (d, 1H); m/z: 255(M+H) +; IR phy using 60-120 silica mesh, the pure product was eluted at 25% of ethyl
(KBr) cm-1 : 3530 (-OH, br), 1732(C=O of lactone ring), 1435 (CH=CH), acetate in pet ether to afford 400mg (45.7%) of 8-acetyl-4, 7-dihydroxy-3-
1150 (C-O-C). phenyl-chromen-2-one (7) as brown color solid.

Preparation of acetic acid 4-acetoxy-2-oxo-3-phenyl-2H-chromen-7-yl
ester (6):
Acetic anhydride (1.8mL, 17.71mmol) was added to a solution of 4, 7-
dihydroxy-3-phenyl-chromen-2-one (5) (1.5g, 5.90mmol) in dry pyridine at
0C. The reaction mixture was wormed to room temperature and stirred for
4h. To this reaction mixture ice cold water added, solid precipitated out. The
solid was filtered and washed with water, dried to afford 1.8g (94.7%) of
acetic acid 4-acetoxy-2-oxo-3-phenyl-2H-chromen-7-yl ester (6) as white
solid.
1
H-NM.R-(400MHz) in DMSO-d6 : 8.08 (d, 1H); 7.52-7.36 (m, 5H);
7.28(d, 2H); 2.34 (s, 3H); 2.32 (s, 3H); m/z: 339 (M+H) +; IR (KBr) cm-1 :
2978 (CH str. Of CH3 ), 1732(C=O of lactone ring), 1718 (C=O of diester);
1456 (CH=CH), 1175 (C-O-C).
Preparation of 8-acetyl-4, 7-dihydroxy-3-phenyl-chromen-2-one (7):
A mixture of AlCl3 (1.57g, 11.83mmol) and acetic acid -4-acetoxy-2-oxo-
phenyl-2H-chromen-7-yl ester (6) (1.0g, 2.95mmol) was heated at 160C
for 1h. The black residue was allowing to cool to room temperature, added
2N HCl (10mL) and heated to 100C for 2h. The reaction mixture allows to
room temperature and filtered the mass and the filterate was extracted with
ethyl acetate (3x30mL). The combined organic layers washed with water and
H1 -NMR-(400MHz) in CDCl3 : 7.97 (d, 1H); 7.78 (d, 1H); 7.51-7.41 (m,
5H); 2.35 (s, 3H); 13 C-NMR in CDCl3 : 29.60, 105.24, 107.33, 116.76,
117.32, 124.82, 129.90, 133.40,135.58, 148.54, 159.26, 163.25, 192.12; m/
z: 295 (M-H)-; ESI-HRMS: m/z Calcd. For C17 H12 O5 [M-H] -295.0814;
Found: 295.0821, IR (KBr) cm-1 : 3580 (-OH, br), 2933 (CH str. Of CH3 ),
1725 (C=O of lactone ring) , 1692 (C=O), 1450 (CH=CH).
Preparation of acetic acid 7-acetoxy-8-acetyl-2-oxo-3-phenyl-2H-
chromen-4-yl ester (8):
Acetic anhydride (0.95mL, 10.13mmol) was added to a solution of 8-acetyl-
4, 7-dihydroxy-3-phenyl-chromen-2-one (7) (1.0g, 3.37mmol) in dry pyri-
dine at 0C. The reaction mixture was wormed to room temperature and
stirred for 4h. To this mixture ice cold water was added, the solid precipitated
out. The solid was filtered and dried to afford 1.0g (78.1%) of acetic acid 7-
acetoxy-8-acetyl-2-oxo-3-phenyl-2H-chromen-4-yl ester (8) as light brown
color solid.
1
H-NMR-(400MHz) in CDCl3 : 7.76 (s, 1H); 7.26-7.18 (m, 5H); 6.88 (d,
1H); 2.36 (s, 3H); 2.16 (s, 6H): m/z: 381 (M+H) +; IR (KBr) cm-1 : 2933 (CH
str. Of CH3 ), 1731 (C=O of diester); 1717 (C=O of lactone ring), 1702
(C=O), 1456 (CH=CH).

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 Jalapathi Pochampalli et al. / Journal of Pharmacy Research 2012,5(4),1957-1962
Preparation of acetic acid 7-hydroxy-2-oxo-8-(3-oxo-butytyl)-3-phenyl-
2H-chromen-4-yl ester (9):
A suspension of Sodium hydride (105mg, 2.63mmol) in dry THF (5mL) was
added to a solution of acetic acid 7-acetoxy-8-acetyl-2-oxo-3-phenyl-2H-
chromen-4-yl ester (8) (500mg, 1.315mmol) in dry THF (10mL) at 0C. The
reaction mixture heated to 65C for 2h, The mixture was allowed to room
temperature and quenched with saturated NH4 Cl solution and extracted with
ethyl acetate (3x25mL), the combined organic layers dried over anhydrous
Na2 SO4 , concentrated under reduced pressure to afford 380mg (76%) of
acetic acid 7-hydroxy-2-oxo-8-(3-oxo-butytyl)-3-phenyl-2H-chromen-4-yl
ester (9) as a light brown color solid.
1
H-NMR-(400MHz) in DMSO-d6 : 7.60(d, 2H); 7.48 (d, 1H); 7.19 (t,
2H); 7.03 (d, 1H); 6.59 (d, 1H); 2.78 (s, 2H); 2.33 (s, 6H); 13 C-NMR in
DMSO-d6 : 19.20, 27.98, 58.90, 107.73, 115.76, 118.32, 124.82, 128.10,
133.10,134.58, 148.74, 152.06, 157.25, 159.00, 163.22, 193.61, 198.78; m/
z: 295 (M-H)-, ESI-HRMS: m/z Calcd. For C21 H16 O7 [M-H] -379.4087;
Found: 379.4052, m/z: 379 (M-1), IR (KBr) cm-1 : 3510 (-OH, br), 2933 (CH
str. Of CH3 ), 1740 (C=O of ester), 1725 (C=O of lactone ring) , 1692 (C=O),
1450 (CH=CH).
Preparation of acetic acid 7-hydroxy-8-(5-methyl-4H-pyrazol-3-yl)-2-
oxo-3-phenyl-2H-chromen-4-yl ester (10):
Hydrazine hydrate (1mL) was added to a solution of acetic acid 7-hydroxy-
2-oxo-8-(3-oxo-butytyl)-3-phenyl-2H-chromen-4-yl ester (9) (100mg,
0.263mmol) in ethanol (5mL) at room temperature and this mixture was
heated at 80C for 2h, after cooling the reaction mixture to room tempera-
ture, evaporated the volatiles, diluted with water and extracted with
chloroform(3x10mL). The combined organic layers dried over Na2 SO4 and
concentrated to afford 72mg (73%) of acetic acid 7-hydroxy-8-(5-methyl-
4H-pyrazol-3-yl)-2-oxo-3-phenyl-2H-chromen-4-yl ester (10) as off white
color solid.
1
H-NMR-(400MHz) in CDCl3 : 7.49(d, 1H); 7.36-7.28 (m, 5H); 6.88 (d,
1H); 2.92 (s, 2H); 2.26 (s, 3H); 1.94 (s, 3H); 13 C-NMR in CDCl3 : 20.40,
24.38, 34.43, 110.43, 116.46, 120.32, 124.92, 127.09, 131.71,133.58, 133.98,
149.54, 153.66, 159.75, 160.60, 166.22, 168.87; m/z: 377 (M+H) +, Anal.
Calcd. For C21 H16 O5 N2 (376): C, 67.02; H, 4.25; N, 7.44 %. Found: C, 67.05;
H, 4.28; N, 7.37%.IR (KBr) cm-1 : 3458 (-OH, br), 2963 (CH str), 1765 (C=O
of ester), 1726 (C=O of lactone ring) , 1599 (C=N), 1442 (CH=CH).
Preparation of acetic acid 7-hydroxy-8-(5-methyl-4, 5-dihydro-osoxazol-
3-yl)-2-oxo-3-phenyl-2H-chromen-4-yl ester (11): Hydroxylamine so-
lution (50% in Aq. 1mL) was added to a solution of acetic acid 7-hydroxy-2-
oxo-8-(3-oxo-butytyl)-3-phenyl-2H-chromen-4-yl ester (9) (100mg,
0.263mmol) in ethanol (5mL) at room temperature and this mixture was
heated at 80C for 6h, after cooling the reaction mixture to room tempera-
ture, evaporated the volatiles, diluted with water and extracted with
chloroform(3x10mL). The combined organic layers dried over Na2 SO4 and
concentrated and recrystalized with methanol to afford 67mg (67.5%) of
acetic acid 7-hydroxy-8-(5-methyl-4, 5-dihydro-osoxazol-3-yl)-2-oxo-3-
phenyl-2H-chromen-4-yl ester (11)as brown color solid.
1
H-NMR-(400MHz) in CDCl3 : 7.61-7.25 (m, 5H); 7.01 (d, 1H); 6.58 (d,
1H); 5.43 (s, 1H); 2.28 (s, 3H); 1.82 (s, 3H); 13 C-NMR in CDCl3 : 14.87,
21.30, 98.63, 111.46, 112.92, 115.87, 118.65, 126.42, 127.79, 132.21,133.48,
146.14, 157.06, 159.65, 162.80, 165.22, 168.96; m/z: 378 (M+H) +; Anal.
Calcd. For C21 H15 O6 N (377): C, 66.84; H, 3.97; N, 3.71%; Found: C, 66.78;
H, 4.02; N, 3.66 %; IR (KBr) cm-1 : 3420 (-OH, br), 2926 (CH str.), 1750
(C=O of ester), 1720 (C=O of lactone ring) , 1619 (C=N), 1468(CH=CH),
1167 (C-O-C).
Journal of Pharmacy Research Vol.5 Issue 4.April 2012
Preparation of acetic acid 7-hydroxy-8-(5-methyl-1-phenyl-1H-pyrazol-
3-yl)-2-oxo-3-phenyl-2H-chromen-4-yl ester (12):
phenyl hydrazine solution (0.081mL, 0.783mmol) was added to a solution
of acetic acid 7-hydroxy-2-oxo-8-(3-oxo-butytyl)-3-phenyl-2H-chromen-
4-yl ester (9) (100mg, 0.263mmol) in ethanol (5mL) at room temperature and
this mixture was heated at 80C for 4h, after cooling the reaction mixture to
room temperature, evaporated the volatiles, diluted with water and extracted
with chloroform(3x10mL). The combined organic layers dried over Na2 SO4
and concentrated and purified by column chromatography using neutral
alumina, the pure compound elute at 4% menthol in dichloromethane to
afford 82mg (68.3%) acetic acid 7-hydroxy-8-(5-methyl-1-phenyl-1H-
pyrazol-3-yl)-2-oxo-3-phenyl-2H-chromen-4-yl ester (12)as brown color
solid.
1
H-NMR-(400MHz) in CDCl3 : 7.76-7.70(m, 5H); 7.68-7.62 (m, 5H)
6.98 (d, 2H); 5.46 (s, 1H); 2.14 (s, 3H); 1.98 (s, 3H); 13 C-NMR in CDCl3 :
14.82, 19.65, 96.23, 110.96, 112.02, 114.67, 118.05, 119.34, 120.42, 125.69,
127.45, 131.91,132.88, 137.82, 140.22, 147.54, 152.96, 157.65, 161.80,
166.22; m/z: 451 (M-H)-, Anal. Calcd. For C 27 H20 O5 N2 (452): C, 71.68; H,
4.42; N, 6.19%. Found: C, 71.52; H, 4.48; N, 6.24%; IR (KBr) cm-1 : 3453 (-
OH, br), 2926 (CH str.), 17356(C=O of ester), 1720 (C=O of lactone ring) ,
1596 (C=N), 1413 (CH=CH).
Preparation of acetic acid 8-[1-(2,4-dinitro-phenyl)-5-methyl-1H-
pyrazol-3-yl]-7-hydroxy-2-oxo-3-phenyl-2H-cromen-yl ester (13):
2, 4-dinitro phenyl hydrazine (103mg, 0.523mmol) was added to a solution
of acetic acid 7-hydroxy-2-oxo-8-(3-oxo-butytyl)-3-phenyl-2H-chromen-
4-yl ester (9) (100mg, 0.263mmol) in ethanol (10mL) at room temperature
and this mixture was heated at 80C for 1.5h, after cooling the reaction
mixture to room temperature, evaporated the volatiles, diluted with water
and extracted with chloroform(3x10mL). The combined organic layers dried
over Na2 SO4 and concentrated and purified by column chromatography
using neutral alumina, the pure compound elute at 2% menthol in
dichloromethane to afford 75mg (60%) acetic acid 8-[1-(2,4-dinitro-phe-
nyl)-5-methyl-1H-pyrazol-3-yl]-7-hydroxy-2-oxo-3-phenyl-2H-cromen-yl
ester (13)as pale yellow solid.
1
H-NMR-(400MHz) in CDCl3 : 7.80 (s, 1H); 7.63 (d, 1H); 7.58-7.51 (m,
5H); 7.32 (d, 2H); 6.98 (d, 1H); 5.56 (s, 1H); 2.36(s, 3H); 2.08 (s, 3H); 13 C-
NMR in CDCl3 : 14.32, 21.03, 98.43, 107.96, 110.10, 112.67, 116.35,
118.94, 120.42, 126.29, 127.45, 130.91,131.08, 135.82, 136.87, 138.12,
146.64, 150.96, 156.05, 159.23, 163.60, 168.22; m/z: 543 (M+H) +, Anal.
Calcd. For C27 H18 O9 N4 (542): C, 59.77; H, 3.32; N, 10.33%. Found: C,
59.65; H, 3.28; N, 10.32%; IR (KBr) cm-1 : 3436 (-OH, br), 2976 (CH str.),
1747 (C=O of ester), 1720 (C=O of lactone ring) , 1596 (C=N), 1587 (NO2 ),
1411 (CH=CH), 1346 (NO2 ).
Preparation of acetic acid 7-hydroxy-8-(6-methyl-2-oxo-2,5-dihydro-
pyrimidin-4-yl)-2-oxo-3-phenyl-2H-chromen-4-yl ester (14): urea (31mg,
0.523mmol) was added to a solution of acetic acid 7-hydroxy-2-oxo-8-(3-
oxo-butytyl)-3-phenyl-2H-chromen-4-yl ester (9) (100mg, 0.263mmol) in
ethanol (8mL) at room temperature and this mixture was heated at 80C for
12h, after cooling the reaction mixture to room temperature, evaporated the
volatiles, diluted with water and extracted with chloroform(3x10mL). The
combined organic layers dried over Na2 SO4 and concentrated to afford 80mg
(74.7%) of acetic acid 7-hydroxy-8-(6-methyl-2-oxo-2,5-dihydro-pyrimidin-
4-yl)-2-oxo-3-phenyl-2H-chromen-4-yl ester (14)as pale brown solid.
1
H-NMR-(400MHz) in CDCl3 : 7.60-7.52(m, 5H); 7.08 (d, 1H); 6.78 (d,
1H); 2.48 (s, 3H); 1.92 (s, 2H); 1.84 (s, 3H); 13 C-NMR in CDCl3 : 18.82,
20.43, 34.54, 111.82, 116.70, 118.94, 125.90, 126.25,131.88, 135.82, 136.28,
1957-1962
 Jalapathi Pochampalli et al. / Journal of Pharmacy Research 2012,5(4),1957-1962
147.24, 150.96, 156.05, 160.22, 162.80, 165.74, 167.20; m/z: 405 (M+H)+;
Anal. Calcd. For C22 H16 O6 N2 (404): C, 65.34; H, 3.96; N, 6.93%. Found: C,
65.45; H, 3.88; N, 7.19%; IR (KBr) cm-1 : 3444 (-OH, br), 2931 (CH str.),
1737 (C=O of ester), 1720 (C=O of lactone ring) , 1687 (C=O of amide),
16027(C=N), 1405 (CH=CH).
ACKNOWLEDGMENT:
The authors wish to thank the Council of Scientific and Industrial Research
(CSIR) New Delhi, India for awarding SRF for Balanarsimha Doddi.
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Journal of Pharmacy Research Vol.5 Issue 4.April 2012 1957-1962