Reaction of (chloro carbonyl) phenyl ketene with 5-amino pyrazolones: Synthesis, characterization and theoretical studies of 7-hydroxy-6-phenyl-3-(phenyldiazenyl)pyrazolo[1,5-a]pyrimidine-2,5(1H,4H)-dione derivatives

Article abstract of DOI:10.1016/j.molstruc.2016.07.043

New 7-hydroxy-6-phenyl-3-(phenyldiazenyl)pyrazolo[1,5-a]pyrimidine-2,5(1H,4H)-dione derivatives were synthesized from the reaction of (chlorocarbonyl)phenyl ketene and 5-amino pyrazolones in high to excellent yields and short reaction times. Structures of

Full text of DOI:10.1016/j.molstruc.2016.07.043

Accepted Manuscript
Reaction of (chloro carbonyl) phenyl ketene with 5-amino pyrazolones:
Synthesis, characterization and theoretical studies of 7-hydroxy-6-phenyl-3-
(phenyldiazenyl)pyrazolo[1,5-a]pyrimidine-2,5(1H,4H)-dione derivatives
Mahboobeh Zahdifar, Razieh Razavi, Hassan Sheibani
PII:
S0022-2860(16)30724-4
10.1016/j.molstruc.2016.07.043
MOLSTR 22746
DOI:
Reference:
To appear in: Journal of Molecular Structure
Received Date: 4 June 2016
Revised Date: 3 July 2016
Accepted Date: 12 July 2016
Please cite this article as: M. Zahdifar, R. Razavi, H. Sheibani, Reaction of (chloro carbonyl) phenyl
ketene with 5-amino pyrazolones: Synthesis, characterization and theoretical studies of 7-hydroxy-6-
phenyl-3-(phenyldiazenyl)pyrazolo[1,5-a]pyrimidine-2,5(1H,4H)-dione derivatives, Journal of Molecular
Structure (2016), doi: 10.1016/j.molstruc.2016.07.043.
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ACCEPTED MANUSCRIPT

ACCEPTED MANUSCRIPT
Reaction of (chloro carbonyl) phenyl ketene with 5-amino pyrazolones:
synthesis, characterization and theoretical studies of 7-hydroxy-6-phenyl-3-
(phenyldiazenyl)pyrazolo[1,5-a]pyrimidine-2,5(1H,4H)-dione derivatives
Mahboobeh Zahdifar1*, Razieh Razavi1 and Hassan Sheibani2
1
Department of Chemistry, Faculty of Science University of Jiroft, Jiroft, 7867161167, Iran. 2 Department of
Chemistry, Shahid Bahonar University of Kerman, 76169 Kerman, Iran.
*E-mail: mzahedi@ujiroft.ac.ir
Abstract
New 7-hydroxy-6-phenyl-3-(phenyldiazenyl)pyrazolo[1,5-a]pyrimidine-2,5(1H,4H)-dione
derivatives were synthesized from the reaction of (chlorocarbonyl)phenyl ketene and 5-amino
pyrazolones in high to excellent yields and short reaction times. Structures of the new
compounds were fully characterized by their spectral data IR, 1H NMR, and 13C NMR and by the
theoretical results. Density Functional Theory (DFT) was used to optimize the structures,
1
compute the energies and vibrational frequencies IR and H NMR shielding tensors of the
desired products. The theoretical results excellent are compared with the experimental data.
Keywords: pyrazolo[1,5-a]pyrimidine; (chlorocarbonyl)phenyl ketene; Density Functional
Theory; 5-amino pyrazolones
1. Introduction
(Chlorocarbonyl)ketenes are versatile bifunctional reagents for the synthesis of numerous
heterocyclic compounds. The reactions of bisnucleophiles with these ketenes leads to cyclic
compounds, which have been reported in several papers.[1, 2] (Chlorocarbonyl)phenyl ketene
has been used mainly for the synthesis of five and six membered heterocycles functionalized
with oxo and hydroxyl groups in 1,3-positions. The reactions of binucleophiles with this ketene
lead to the synthesis of heterocyclic compounds.[3, 4] Structures containing such units often play
1

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an essential role due to their biological activity, predominantly in cancer and virus research.[5, 6]
Pyrazole derivatives are one of the important class of heterocyclic compounds. This compounds
can be used as the intermediate in organic synthesis and possess a range of interesting biological
and antimicrobial properties.[7-10] a massive search for new anticancer agents has been fueled
by various academics and industries to unveil the new molecular targets and mechanisms based
on the lead candidates of different classes of compounds. A large number of pyrazolo[1,5-
a]pyrimidine derivatives are reported to exhibit a broad spectrum of biological activities such as
antitumor, [11, 12] anxiolytic [13]and antimicrobial. [14] But pyrazolo[1,5-a]pyrimidine
derivatives are widely used as inhibitors of cyclin-dependent kinases (CDKs), that are involved
in mediating the transmission of mitogenic signals and numerous other cellular events [15-18]
including cell proliferation, migration, differentiation, metabolism and immune response. Some
their fused pyrimidine derivatives are used as dyes.[19-23] Due to the biological activities of
pyrazolo[1,5-a]pyrimidine derivatives new ways for the synthesis of these compounds have been
of interest. So in order to access analogs of pyrimidine fused to pyrazole rings, the reaction of
(chlorocarbonyl)phenyl ketene with 5-aminopyrazole-3-one derivatives was investigated in this
paper.
2. Experimental
Phenyl malonic acid, aniline derivatives, ethyl cyanoacetate and hydrazine hydrate were
obtained from Merck Chemical Co. and were used without further purification.
(Chlorocarbonyl)phenyl ketenes 2 were prepared according to the literature procedure.[24] The
5-amino-1,2-dihydro-3H-pyrazol-3-one derivatives 1a-e were known and prepared according to
the general procedure reported in the literature.[25] THF was dried over sodium and distilled
prior to use. Melting points were measured on an Electrothermal-9100 apparatus and are
uncorrected. IR spectra were recorded on a Brucker FT-IR Tensor 27 infrared
spectrophotometer. The proton and carbon NMR spectra were recorded with Bruker DRX-400
spectrometer (400 and 100 MHz, respectively) in DMSO-d6, internal standard TMS. Elemental
analyses were carried out using a Heraeus CHN-O-Rapid analyzer.
2.1. Theoretical method:
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All geometry optimizations and quantum chemical calculations were performed through
Gaussian 09 software[26] using density functional theory (DFT) with B3LYP/6-311G quantum
level. The B3LYP(Becke’s hybrid 3-parameter functional with Lee-Yang-Parr
correlation)functional was selected for the calculations. B3LYP has been introduced as one of
the most accurate methods for energy calculation. Structure parameters have been calculated by
optimizing type job in Gaussian package. For Thermodynamic properties (∆G) and IR spectrum,
frequency type job at Gaussian package has been done and NMR data have obtained by NMR
type job with the same method.
2.2. Typical procedure for the preparation of compounds (3a-c)
To a stirred solution of corresponding 5-amino-1,2-dihydro-3H-pyrazol-3-one derivatives 1
(2 mmol) in 20 mL boiling dry THF was added a mixture of (chlorocarbonyl)phenyl ketene 2 (2
mmol) in 5ml dry THF dropwise over 2 min. The product was formed after 5 minutes as a
colored precipitate. Stirring was then continued for an additional 15 minutes. The solid product
was collected and recrystallized from dry ethyl acetate and hexane (2:3).
2.3. 7-hydroxy-6-phenyl-3-(phenyldiazenyl)pyrazolo[1,5-a]pyrimidine-2,5(1H,4H)-dione (3a)
The 0.29 g (85%) red crystals, IR (KBr): 3200-2900 (NH, OH), 1657 (C=O), 1625, 1550,
1481 cm-1. 1H NMR (400 MHz, DMSO-d6): δ (ppm): 10.01 (1H, s, NH), 9.32 (1H, s, OH), 8.17-
3
3
6.97(10H, m, arom, NH)[8.16 (2H, d, JH-H=8Hz), 8.87 (2H, d, JH-H=8Hz), 7.46-7.43 (3H, m),
3
7.29-7.23 (3H, m), 7.98 (1H, t, JH-H=8Hz)]. 13C NMR (100 MHz, DMSO-d6): δ (ppm): 160.04,
159.80, 151.36, 145.94, 143.69, 134.35, 129.22, 127.51, 126.88, 123.31, 123.01, 117.76, 84.32,
67.93. Anal. Calcd for. C17H13NO3S: C, 62.24; H, 3.77; N, 20.16; O, 13.82%. Found: C, 62.02;
H. 3.59; N; 20.01 %.
2.4. 7-hydroxy-3-((4-methoxyphenyl)diazenyl)-6-phenylpyrazolo[1,5-a]pyrimidine-2,5(1H,4H)-
dione (3b)
The 034 g (90%) dark violet crystals, IR (KBr): 3200-2900 (NH, OH), 1668 (C=O), 1628,
1554, 1491 cm-1. 1H NMR (400 MHz, DMSO-d6): δ (ppm): 9.79 (1H, s, NH), 9.09 (1H, s, OH),
8.16-6.95(10H, m, arom, NH) [8.16 (2H, d, 3JH-H=4Hz), 7.83 (2H, d, 3JH-H=8Hz), 7.73-7.21 (3H,
3
3
13
m), 7.01 (2H, d, JH-H=8Hz), 6.97 (1H, t, JH-H=8Hz)], 3.38 (3H, s, methoxy). C NMR (100
3

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MHz, DMSO-d6): δ (ppm): 160.58, 160.48, 158.78, 150.49, 146.20, 134.59, 129.26, 126.48,
123.32, 119.88, 118.51, 114.70, 84.26, 66.30, 55.46. Anal. Calcd for. C19H15N5O4: C, 60.48; H,
4.01; N, 18.56; O, 16.96 %. Found: C, 60.31; H. 4.16; N; 18.39%.
2.5.
dione (3c)
The 0.34 g (90%) dark violet crystals, IR (KBr): 3200-2900 (NH, OH), 1672 (C=O), 1593,
1549, 1484 cm-1. 1H NMR (400 MHz, DMSO-d6): δ (ppm): 9.77 (1H, s, NH), 9.06 (1H, s, OH),
3-((4-chlorophenyl)diazenyl)-7-hydroxy-6-phenylpyrazolo[1,5-a]pyrimidine-2,5(1H,4H)-
3
3
8.15-6.96(10H, m, arom, NH) [8.14 (2H, d, JH-H=8Hz), 7,85 (2H, s), 7.48 (2H, d, JH-H=8Hz),
13
7.33-7.22 (2H, m), 6.96 (2H, s)]. C NMR (100 MHz, DMSO-d6): δ (ppm): 161.13, 160.35,
151.36, 145.54, 134.50, 131.10, 130.39, 129.54, 127.48, 123.26, 120.23, 116.85, 84.27, 67.64.
Anal. Calcd for. C18H12ClN5O3: C, 56.63; H, 3.17; Cl, 9.29; N, 18.34; O, 12.57%. Found: C,
56.51; H. 3.02; N; 18.25%.
2.6. 7-hydroxy-6-phenyl-3-(p-tolyldiazenyl)pyrazolo[1,5-a]pyrimidine-2,5(1H,4H)-dione (3d)
The 0.31 g (88%) violet crystals crystals, IR (KBr): 3200-2900 (NH, OH), 1672 (C=O),
1
1628, 1552, 1492 cm-1. H NMR (400 MHz, CDCl3): δ (ppm): 9.96 (1H, s, NH), 9.25 (1H, s,
OH), 8.17-6.97(10H, m, arom, NH) [7.16 (2H, d, 3JH-H=8Hz), 7.76 (2H, d, 3JH-H=8Hz), 7.24 (4H,
3
3
13
t, JH-H=8Hz), 6.98 (2H, t, JH-H=4Hz) , 2.49 (3H, s, methyl). C NMR (100 MHz, CDCl3): δ
(ppm): 160.08, 159.85, 151.31, 146.12, 141.10, 136.81, 134.47, 129.80, 127.61, 123.40, 123.10,
117.77, 84.40, 64.85, 20.62. Anal. Calcd for. C19H15N5O3: C, 63.15; H, 4.18; N, 19.38; O,
13.28%. Found: C, 63.01; H. 4.10; N; 19.29%
2.7.
4-((7-hydroxy-2,5-dioxo-6-phenyl-1,2,4,5-tetrahydropyrazolo[1,5-a]pyrimidin-3-
yl)diazenyl) benzenesulfonamide (3e)
The 0.35 (82%) dark violet crystals, IR (KBr): 3639, 3547 (NH2), 3300-2800 (NH, OH),
1
1688 (C=O), 1630, 1596, 1486 cm-1. H NMR (400 MHz, DMSO-d6): δ (ppm): 10.08 (1H, s,
NH), 9.32 (1H, s, OH), 8.16-6.96 (12H, m, arom, NH, NH2) [8.16 (2H, d, 3JH-H=4Hz), 8.00 (2H,
3
3
3
d, JH-H=4Hz), 8.87 (2H, d, JH-H=4Hz), 7.41 (2H, s, NH2), 7.29-7.22 (3H, m), 6.98 (1H, t, JH-
H=8Hz). 13C NMR (100 MHz, DMSO-d6): δ (ppm): 160.52, 160.43, 153.78, 145.48, 141.66,
134.48, 130.52, 129.82, 128.29, 127.60, 123.42, 118.41, 84.48, 67.02. Anal. Calcd for.
4

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C18H14N6O5S: C, 50.70; H, 3.31; N, 19.71; O, 18.76; S, 7.52%. Found: C, 50.54; H. 3.16; N;
19.88%.
3. Result and Discussion
Synthesis of 5-aminopyrazoles 3 is readily available by diazotiazation of aniline derivatives
1a-e followed by coupling with ethyl cyanoacetate, affording the corresponding hydrazones 2a-
e. Reaction of compounds 2 with hydrazine hydrate undergoes corresponding 5-aminopyrazoles
3a-e [25] in good yields, scheme 1.
XC6H4 N N
N2H4
NH2
NH
CN
CN
NaNO2/HCl
H
CO2Et
+
XC6H4 N2 Clꢀ
XC6H4NH2
XH4X6 N N
O
CO2Et
N
H
1a: X=H
1b: X=OCH3
1c: X=Cl
3aꢀe
2aꢀe
1d: X=CH3
1e: X=SO2NH2
Scheme 1. Synthesis of 5-aminopyrazoles 3a-e from aniline derivatives.
In connection with our ongoing work on the development of new synthetic routes to
heterocyclic compounds by condensation of (chlorocarbonyl)ketenes with 1,3-
4
dinucleophiles,[1, 3, 4] we report herein the reaction of (chlorocarbonyl)ketenes 4 with 5-
aminopyrazoles 3 for the synthesis of 7-hydroxy-6-phenyl-3-(phenyldiazenyl)pyrazolo[1,5-
a]pyrimidine-2,5(1H,4H)-dione derivatives 5a-e, scheme 2.
Scheme 2. Synthesis of 7-hydroxy-6-phenyl-3-(aryldiazenyl)pyrazolo[1,5-a]pyrimidine-
2,5(1H,4H)-dione derivatives 5 from the reaction of (chlorocarbonyl)phenyl ketene 4 and 5-
amino-4-(aryldiazenyl)-1,2-dihydro-3H-pyrazol-3-one derivatives 3
5

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A literature survey indicates that only a few references are available on the synthesis and
chemistry of pyrazolo[1,5-a]pyrimidine derivatives[27]. In this method, 7-hydroxy-6-phenyl-3-
(aryldiazenyl)pyrazolo[1,5-a]pyrimidine-2,5(1H,4H)-dione derivatives 5a-e have been produced
from the one-pot cyclocondensation of (chlorocarbonyl)phenyl ketene 4 and 5-amino-4-
(aryldiazenyl)-1,2-dihydro-3H-pyrazol-3-one derivatives 3. The simplicity and efficient one-pot
procedure is one aspect of particular interest, in comparison to the other multi-step methods. On
the other hand, readily available starting materials such as (chlorocarbonyl)phenyl ketene,
shorten experimental time, and high yield of the final products are the other advantages of this
method. When (chlorocarbonyl)phenyl ketenes 4 were added to a solution of the 5-
aminopyrazolone derivatives 3 at boiling solvent, precipitate of the product was formed
immediately.
A plausible mechanism for the formation of the product 5 is outlined in scheme 3. 5-
aminopyrazolones have three sites of electron rich positions, at the nitrogen atoms. Nucleophilic
reactions on these compounds can take place on either of the exocyclic or the endocyclic
nitrogen atoms. Here, the endocyclic nitrogen atom will attack the central carbon atom of the
ketene group, which possesses a low-lying LUMO. Subsequent cyclization affords compound II.
H+ elimination gives compound 5.
Scheme 3. Proposed mechanism for the formation of 7-hydroxy-6-phenyl-3-(aryldiazenyl)
pyrazolo[1,5-a]pyrimidine-2,5(1H,4H)-dione 5
6

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The structures of compounds 5a–e were determined on the basis of their elemental analyses,
13
1
1H- and C-NMR and IR spectral data. Only one product was obtained in each case. The H
NMR spectrum of 5a-e indicated two signal at low field (10-9 ppm) attributed to the OH and NH
groups.
In the present work, DFT/B3LYP approach was employed by using Gaussian 09 software. At
first, the different possible conformers was considered and optimized for the synthesized
products and then stable conformer was employed to calculate the vibrational frequencies and
NMR spectrum to confirm that the reported structures are true minima. Obtained positive first
frequency for each compound in frequency type job output data confirmed accurately true minima .[28]
To predict the spectroscopic properties of the most stable structure, DFT approach was used in
the Gaussian software. The computed wavenumbers were scaled with the scaling factor in order
to figure out how the predicted vibrational spectra are in agreement with experimental ones.
Vibrational analysis of molecule was computed by using B3LYP level with basis set 6-311 G.
The detected and predicted vibrational spectrum with results of fundamental vibrational modes
were given in table 1 and figure 1.
As shown in table 1, the experimental N-H and O-H stretching frequencies appeared in the
range of 3300-2800ꢁcm−1 for compound 5a-e, the theoretically predicted IR for N-H and O-H
stretching frequencies also were observed in the same range ~ 3199-2902 cm-1 by B3LYP/6-311
G. The frequencies characteristics of the C=O stretching modes were observed in the range of
1690-1650ꢁcm−1 in the experimental part which is in good correlation with B3LYP/6-311 G
studies, 1690-1650ꢁcm−1. For example, in the case of compound 5d, the experimental C=O
stretching frequencies appeared in 1672 cm-1 and the theoretically C=O stretching frequencies
was appeared in 1669 cm-1 (figure 1). The strongly intense peaks from B3LYP/6-311+G(d,p)
agree well to the intensities obtained experimentally. In this calculations, chemical shifts value
were predicted by ‘‘Gauge-Independent Atomic Orbital’’ (GIAO).
7

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Experimental IR(cm-1)
Theoretical IR(cm-1)
B3LYP/6-311G
Compound
5a
(NH,OH) 3200-2900,(C=O)
1657, 1625, 1481, 1550
(NH,OH) 3209-2902, (C=O)
1651, 1660, 1624, 1633,
1543, 1552, 1480, 1489
(NH,OH) 3200-2900, (C=O) (NH,OH) 3199-2893, (C=O)
5b
5c
5d
5e
1668, 1628, 1554, 1491
1669, 1624, 1633, 1552,
1489,1498
(NH,OH)3200-2900, (C=O)
1672, 1593, 1549, 1484
(NH,OH) 3208-2902, (C=O)
1670, 1679, 1588, 1597,
1543, 1480, 1489
(NH,OH) 3200-2900, (C=O) (NH,OH) 3207-2902, (C=O)
1672, 1628, 1552, 1492
1669,1678, 1624, 1633, 1552,
1561, 1489, 1498
(NH2) 3639, 3547, (NH, OH) (NH,OH) 3325-2803, (C=O)
3300-2800, (C=O) 1688,
1630, 1596, 1486
1687, 1624, 1633, 1642,
1588, 1597, 1480,1489
Table 1
Calculated IR frequency of synthesized compound by B3LYP/6-311G
Figure 1. The calculated and the experimental IR spectra of compound 5d
8

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The Nuclear Magnetic Resonance spectra of the ground state geometry of molecule have
been obtained by DFT/GIAO method. The GIAO method is one of the most common methods
for calculating isotropic nuclear magnetic. The predicted and measured NMR values were listed
in table 2.
The investigated compounds contain C=O and C=C-OH group, the oxygen atom causes an
increase in the chemical shift of the carbon atom band. This is evidence for a decrease in the
electron density around this atom. So, C-2, C-5, and C-7 appeared around 160-150 ppm in
experimental CNMR data. The theoretical CNMR data for C-2, C-5 and C-7 also appeared
around 160-150 ppm. The aromatic carbon atoms both for experimental and theoretical studies
appeared in 150-100 area. Because of resonance effect, the electron densities around the C-3 and
C-6 atom are higher than for other carbon double bonds, affording the lower chemical shift
values for these atoms, 84 ppm for C-3 and 64-68 ppm for C-6 in experimental data. The
experimental reaction was done in the solution but the theoretical method has been done in the
gas phase and caused to small differences between the calculated and experimentally obtained
chemical shift values in the last. Experimental NMR spectra of molecules are in excellent
agreement with theoretical ones.
Table2
NMR calculated chemical shift by B3LYP/6-311G
Experimental NMR(ppm)
13C NMR
Theoretical NMR(ppm) B3LYP/6-311G
13C NMR
5a
160.04
159.80
151.36
145.94
143.69
134.35
129.22
127.51
126.88
123.31
123.01
117.76
5b
5c
5d
5e
5a
5b
5c
5d
5e
160.58 161.13
160.48 160.35
158.78 151.36
150.49 145.54
146.20 134.50
134.59 131.10
129.26 130.39
126.48 129.54
123.32 127.48
119.88 123.26
118.51 120.23
114.70 116.85
160.08 160.52 159.71 159.06 159.51 159.83 159.00
159.85 160.43 154.94 157.75 152.63 153.00 156.16
151.31 153.78 149.63 149.75 149.28 149.69 155.05
146.12 145.48 145.92 149.24 146.56 145.66 148.70
141.10 141.66 130.44 140.89 146.12 136.29 147.12
136.81 134.48 129.65 132.99 130.44 130.45 130.50
134.47 130.52 128.24 129.31 130.05 129.96 127.93
129.80 129.82 127.96 128.17 129.69 128.73 126.36
127.61 128.29 126.29 127.62 127.68 128.15 125.68
123.40 127.60 125.97 123.34 126.08 126.90 122.12
123.10 123.42 124.19 118.31 125.51 125.90 120.93
117.77 118.41 115.81 116.19 115.83 115.76 115.94
9

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84.32
67.93
84.26 84.27
66.30 67.64
55.46
84.40
64.85
20.62
84.48 110.77 104.55 110.85 110.29 108.90
67.02 100.40 96.46
50.13
101.71 100.34 103.17
15.37
The optimized geometries of the desired products are depicted in figure 2.
Figure 2. The optimized geometries of the compounds 5a-e
Table 3 indicated Gibbs free energy for each compound at 298K. According to these data of
this table, Fig 2 was shown the activity energy surface of doing the reaction .Energy surface of
the product is higher than the reactant energy surface at room temperature. This happen obtained
the reaction will be done by external energy. Therefore for the experimental process must use
boiling point of THF used for synthesis reaction.
Table 3
Gibbs free energy of all compound calculated by B3LYP/6-311G at 298K in gas phase
Comp
4
3a
3b
3c
3d
3e
5a
5b
5c
5d
5e
THF HCl
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-6.53
-2.51 -1.83 -6.70 -4.86
-1.04 -3.13 -3.43 -4.34 -6.67 -4.72 -6.10 -1.21
ꢁG˚f
(j)×104
Figure 3. Activity energy surface of reactant and product in THF
4. Conclusion
In conclusion, we have presented the condensation of (chlorocarbonyl)phenyl ketene 4 with
1,2-bisnucleophilic 5-amino pyrazolone compounds 3, affording a convenient and rapid
synthesis of pharmacologically interesting 7-hydroxy-6-phenyl-3-(phenyldiazenyl)pyrazolo[1,5-
a]pyrimidine-2,5(1H,4H)-dione derivatives 5 in excellent yields. Also, no cumbersome apparatus
is needed and the desired product precipitated from the reaction mixtures and their purification is
straightforward. Furthermore, Calculated Gibbs free energy accordance with experimental
11

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process showed this reaction can be done at the boiling point of THF. Additionally, Vibration
frequencies recognized the experimental products of this reaction with different substitutes can
be produced and has the best accordance with empirical spectrum. NMR data also showed the
products in the experimental method are correct products of this reaction. Calculated parameters
predicted that this reaction theoretically suitable for experimental synthesis.
Acknowledgements
The authors express appreciation to the University of Jiroft Faculty Research Committee and
Shahid Bahonar University of Kerman for supporting this investigation.
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Highlights
•
Highly efficient synthesis of pharmacologically interesting 7-hydroxy-6-phenyl-3-
(phenyldiazenyl)pyrazolo[1,5-a]pyrimidine-2,5(1H,4H)-dione derivatives
Easy product separation and purification.
•
•
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Excellent yields and short reaction time.
Excellent agreement of experimental results with theoretical ones.