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

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

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

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

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Preparation of acetic acid 7-hydroxy-2-oxo-8-(3-oxo-butytyl)-3-phenyl- Preparation of acetic acid 7-hydroxy-8-(5-methyl-1-phenyl-1H-pyrazol-
2H-chromen-4-yl ester (9): 3-yl)-2-oxo-3-phenyl-2H-chromen-4-yl ester (12):
A suspension of Sodium hydride (105mg, 2.63mmol) in dry THF (5mL) was phenyl hydrazine solution (0.081mL, 0.783mmol) was added to a solution
added to a solution of acetic acid 7-acetoxy-8-acetyl-2-oxo-3-phenyl-2H- of acetic acid 7-hydroxy-2-oxo-8-(3-oxo-butytyl)-3-phenyl-2H-chromen-
chromen-4-yl ester (8) (500mg, 1.315mmol) in dry THF (10mL) at 0C. The 4-yl ester (9) (100mg, 0.263mmol) in ethanol (5mL) at room temperature and
reaction mixture heated to 65C for 2h, The mixture was allowed to room this mixture was heated at 80C for 4h, after cooling the reaction mixture to
temperature and quenched with saturated NH4 Cl solution and extracted with room temperature, evaporated the volatiles, diluted with water and extracted
ethyl acetate (3x25mL), the combined organic layers dried over anhydrous with chloroform(3x10mL). The combined organic layers dried over Na2 SO4
Na2 SO4 , concentrated under reduced pressure to afford 380mg (76%) of and concentrated and purified by column chromatography using neutral
acetic acid 7-hydroxy-2-oxo-8-(3-oxo-butytyl)-3-phenyl-2H-chromen-4-yl alumina, the pure compound elute at 4% menthol in dichloromethane to
ester (9) as a light brown color solid. 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
1
H-NMR-(400MHz) in DMSO-d6 : 7.60(d, 2H); 7.48 (d, 1H); 7.19 (t, solid.
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, 1
H-NMR-(400MHz) in CDCl3 : 7.76-7.70(m, 5H); 7.68-7.62 (m, 5H)
133.10,134.58, 148.74, 152.06, 157.25, 159.00, 163.22, 193.61, 198.78; m/ 6.98 (d, 2H); 5.46 (s, 1H); 2.14 (s, 3H); 1.98 (s, 3H); 13 C-NMR in CDCl3 :
z: 295 (M-H)-, ESI-HRMS: m/z Calcd. For C21 H16 O7 [M-H] -379.4087; 14.82, 19.65, 96.23, 110.96, 112.02, 114.67, 118.05, 119.34, 120.42, 125.69,
Found: 379.4052, m/z: 379 (M-1), IR (KBr) cm-1 : 3510 (-OH, br), 2933 (CH 127.45, 131.91,132.88, 137.82, 140.22, 147.54, 152.96, 157.65, 161.80,
str. Of CH3 ), 1740 (C=O of ester), 1725 (C=O of lactone ring) , 1692 (C=O), 166.22; m/z: 451 (M-H)-, Anal. Calcd. For C 27 H20 O5 N2 (452): C, 71.68; H,
1450 (CH=CH). 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) ,
Preparation of acetic acid 7-hydroxy-8-(5-methyl-4H-pyrazol-3-yl)-2- 1596 (C=N), 1413 (CH=CH).
oxo-3-phenyl-2H-chromen-4-yl ester (10):
Hydrazine hydrate (1mL) was added to a solution of acetic acid 7-hydroxy- Preparation of acetic acid 8-[1-(2,4-dinitro-phenyl)-5-methyl-1H-
2-oxo-8-(3-oxo-butytyl)-3-phenyl-2H-chromen-4-yl ester (9) (100mg, pyrazol-3-yl]-7-hydroxy-2-oxo-3-phenyl-2H-cromen-yl ester (13):
0.263mmol) in ethanol (5mL) at room temperature and this mixture was 2, 4-dinitro phenyl hydrazine (103mg, 0.523mmol) was added to a solution
heated at 80C for 2h, after cooling the reaction mixture to room tempera- of acetic acid 7-hydroxy-2-oxo-8-(3-oxo-butytyl)-3-phenyl-2H-chromen-
ture, evaporated the volatiles, diluted with water and extracted with 4-yl ester (9) (100mg, 0.263mmol) in ethanol (10mL) at room temperature
chloroform(3x10mL). The combined organic layers dried over Na2 SO4 and and this mixture was heated at 80C for 1.5h, after cooling the reaction
concentrated to afford 72mg (73%) of acetic acid 7-hydroxy-8-(5-methyl- mixture to room temperature, evaporated the volatiles, diluted with water
4H-pyrazol-3-yl)-2-oxo-3-phenyl-2H-chromen-4-yl ester (10) as off white and extracted with chloroform(3x10mL). The combined organic layers dried
color solid. over Na2 SO4 and concentrated and purified by column chromatography
using neutral alumina, the pure compound elute at 2% menthol in
1
H-NMR-(400MHz) in CDCl3 : 7.49(d, 1H); 7.36-7.28 (m, 5H); 6.88 (d, dichloromethane to afford 75mg (60%) acetic acid 8-[1-(2,4-dinitro-phe-
1H); 2.92 (s, 2H); 2.26 (s, 3H); 1.94 (s, 3H); 13 C-NMR in CDCl3 : 20.40, nyl)-5-methyl-1H-pyrazol-3-yl]-7-hydroxy-2-oxo-3-phenyl-2H-cromen-yl
24.38, 34.43, 110.43, 116.46, 120.32, 124.92, 127.09, 131.71,133.58, 133.98, ester (13)as pale yellow solid.
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;
1
H-NMR-(400MHz) in CDCl3 : 7.80 (s, 1H); 7.63 (d, 1H); 7.58-7.51 (m,
H, 4.28; N, 7.37%.IR (KBr) cm-1 : 3458 (-OH, br), 2963 (CH str), 1765 (C=O 5H); 7.32 (d, 2H); 6.98 (d, 1H); 5.56 (s, 1H); 2.36(s, 3H); 2.08 (s, 3H); 13 C-
of ester), 1726 (C=O of lactone ring) , 1599 (C=N), 1442 (CH=CH). 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.
Preparation of acetic acid 7-hydroxy-8-(5-methyl-4, 5-dihydro-osoxazol- Calcd. For C27 H18 O9 N4 (542): C, 59.77; H, 3.32; N, 10.33%. Found: C,
3-yl)-2-oxo-3-phenyl-2H-chromen-4-yl ester (11): Hydroxylamine so- 59.65; H, 3.28; N, 10.32%; IR (KBr) cm-1 : 3436 (-OH, br), 2976 (CH str.),
lution (50% in Aq. 1mL) was added to a solution of acetic acid 7-hydroxy-2- 1747 (C=O of ester), 1720 (C=O of lactone ring) , 1596 (C=N), 1587 (NO2 ),
oxo-8-(3-oxo-butytyl)-3-phenyl-2H-chromen-4-yl ester (9) (100mg, 1411 (CH=CH), 1346 (NO2 ).
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- Preparation of acetic acid 7-hydroxy-8-(6-methyl-2-oxo-2,5-dihydro-
ture, evaporated the volatiles, diluted with water and extracted with pyrimidin-4-yl)-2-oxo-3-phenyl-2H-chromen-4-yl ester (14): urea (31mg,
chloroform(3x10mL). The combined organic layers dried over Na2 SO4 and 0.523mmol) was added to a solution of acetic acid 7-hydroxy-2-oxo-8-(3-
concentrated and recrystalized with methanol to afford 67mg (67.5%) of oxo-butytyl)-3-phenyl-2H-chromen-4-yl ester (9) (100mg, 0.263mmol) in
acetic acid 7-hydroxy-8-(5-methyl-4, 5-dihydro-osoxazol-3-yl)-2-oxo-3- ethanol (8mL) at room temperature and this mixture was heated at 80C for
phenyl-2H-chromen-4-yl ester (11)as brown color solid. 12h, after cooling the reaction mixture to room temperature, evaporated the
volatiles, diluted with water and extracted with chloroform(3x10mL). The
1
H-NMR-(400MHz) in CDCl3 : 7.61-7.25 (m, 5H); 7.01 (d, 1H); 6.58 (d, combined organic layers dried over Na2 SO4 and concentrated to afford 80mg
1H); 5.43 (s, 1H); 2.28 (s, 3H); 1.82 (s, 3H); 13 C-NMR in CDCl3 : 14.87, (74.7%) of acetic acid 7-hydroxy-8-(6-methyl-2-oxo-2,5-dihydro-pyrimidin-
21.30, 98.63, 111.46, 112.92, 115.87, 118.65, 126.42, 127.79, 132.21,133.48, 4-yl)-2-oxo-3-phenyl-2H-chromen-4-yl ester (14)as pale brown solid.
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; 1
H-NMR-(400MHz) in CDCl3 : 7.60-7.52(m, 5H); 7.08 (d, 1H); 6.78 (d,
H, 4.02; N, 3.66 %; IR (KBr) cm-1 : 3420 (-OH, br), 2926 (CH str.), 1750 1H); 2.48 (s, 3H); 1.92 (s, 2H); 1.84 (s, 3H); 13 C-NMR in CDCl3 : 18.82,
(C=O of ester), 1720 (C=O of lactone ring) , 1619 (C=N), 1468(CH=CH), 20.43, 34.54, 111.82, 116.70, 118.94, 125.90, 126.25,131.88, 135.82, 136.28,
1167 (C-O-C).

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 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)+; 9. Marchenko, M. M. ; Kopylchuk, G. P. ; Shmarakov, I. A. ; Ketsa,
Anal. Calcd. For C22 H16 O6 N2 (404): C, 65.34; H, 3.96; N, 6.93%. Found: C, O. V. ; and Kushner, V. N. ; Pharm.Chem. J. 2006, 40, 296-297.
65.45; H, 3.88; N, 7.19%; IR (KBr) cm-1 : 3444 (-OH, br), 2931 (CH str.), 10. L. Huang. ; X. Yuon. ; D. Yu. ; K.H. Lee. ; and H. C. Chin. ;
1737 (C=O of ester), 1720 (C=O of lactone ring) , 1687 (C=O of amide), Virology, 332, 623(2005).
16027(C=N), 1405 (CH=CH). 11. M. A. Bhat. ; N. Siddiqui. ; and S. A. Khan. ; Indian J.Pharm. Sci.,
68, 120(2006).
ACKNOWLEDGMENT: 12. N. S. Habib. ; and M. A. Khalil. ; J. Pharm. Sci., 73, 982(1984).
The authors wish to thank the Council of Scientific and Industrial Research 13. Manohar, K.; Manjunath, G.; and Raviraj, K.; Indian Journal of
(CSIR) New Delhi, India for awarding SRF for Balanarsimha Doddi. Heterocyclic Chemistry; (2004). 13:201-204.
14. Bailey, D. M. ; Hansen, P. E. ; Hlavac, A. G. ; Baizman, E. R. ;
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Source of support: Nil, Conflict of interest: None Declared

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

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