Synthesis of new substituted N-sulfonyl pyrrolidine-2,5-dione using dawson-type heteropolyacid as catalyst

Article abstract of DOI:10.1080/10426507.2014.947413

The synthesis of new series of pyrrolidine-2,5-diones having sulfonamide moieties is described. These compounds are synthesized in good yield in three steps (carbamoylation-sulfamoylation, deprotection and condensation) using a catalytic amount of H₆P₂W₁₈O₆₂ in acetonitrile under refluxing conditions.

Full text of DOI:10.1080/10426507.2014.947413

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Phosphorus, Sulfur, and Silicon and the
Related Elements
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Synthesis of New Substituted N-Sulfonyl
Pyrrolidine-2,5-Dione Using Dawson-Type
Heteropolyacid as Catalyst
Chafika Boughelouma, Robila Belghichea & Abdelrani Messalhia
a LSC, Faculty of Science, Department of Chemistry, Badji Mokhtar-
Annaba University, 23000, Algeria
Accepted author version posted online: 29 Jul 2014.
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To cite this article: Chafika Bougheloum, Robila Belghiche & Abdelrani Messalhi (2015) Synthesis
of New Substituted N-Sulfonyl Pyrrolidine-2,5-Dione Using Dawson-Type Heteropolyacid as
Catalyst, Phosphorus, Sulfur, and Silicon and the Related Elements, 190:3, 269-276, DOI:
10.1080/10426507.2014.947413
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Phosphorus, Sulfur, and Silicon, 190:269–276, 2015
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426507.2014.947413
SYNTHESIS OF NEW SUBSTITUTED N-SULFONYL
PYRROLIDINE-2,5-DIONE USING DAWSON-TYPE
HETEROPOLYACID AS CATALYST
Chafika Bougheloum, Robila Belghiche,
and Abdelrani Messalhi
LSC, Faculty of Science, Department of Chemistry, Badji Mokhtar-Annaba
University, 23000, Algeria
GRAPHICAL ABSTRACT
Abstract The synthesis of new series of pyrrolidine-2,5-diones having sulfonamide moieties
is described. These compounds are synthesized in good yield in three steps (carbamoylation-
sulfamoylation, deprotection and condensation) using a catalytic amount of H6P2W18O62 in
acetonitrile under refluxing conditions.
Keywords Sulfonamide; Dawson heteropolyacid; catalyst; succinic anhydride; pyrrolidine-2;
5-diones
INTRODUCTION
Heterocyclic compounds are important and valuable parts of biologically active
molecules and natural products;1 therefore, the design of new strategies to synthesize
them is currently an important area of research. An interesting class of these compounds is
pyrrolidine-2,5-diones, which are commonly referred to as succinimides; they are charac-
terized by the presence of the fragment -(CO)NR(CO)- as belonging to the five-membered
ring.2
These cyclic imides show great bioactive and pharmacological potential acting as
enzyme inhibitors,3 analgesics,4 antimicrobial agents,5 anxiolytics, 6 cytotoxic,7 but mainly
as anticonvulsants8 (Figure 1).
Received 13 May 2014; accepted 18 July 2014.
Address correspondence to Chafika Bougheloum, Faculty of Sciences, Department of Chemistry, Badji
Mokhtar-Annaba University, BP 12 El Hadjar, 23000, Algeria. E-mail: c bougheloum@yahoo.fr
269

270
C. BOUGHELOUM ET AL.
Figure 1 Anticonvulsant drugs containing the fragment -(CO)NR(CO)-.
Previously, we reported the synthesis of the acyl sulfamides9 via acylation of de-
protected sulfamides with acetic anhydride. In this work, we describe the synthesis of
pyrrolidine-2,5-diones having sulfonamide moieties using an acylating agent.
The sulfonamide group is considered as a pharmacophore, which is present in a
number of biologically active molecules, particularly antimicrobial agents.10
It was shown that sulfonamide moieties can enhance largely the activity of antibacte-
rial agents especially against both Gram-positive and Gram-negative bacteria.11 In addition,
the sulfonamide derivatives constitute an important class of drugs, with several types of
pharmacological agents possessing antibacterial,12 antitumor,13 anticarbonic anhydrase,14
anticonvulsant,15 or protease inhibitory activity16 among others.
A number of synthetic methods have been developed in recent years to uncover a
variety of new reagents for the synthesis of pyrrolidine-2,5-diones derivatives.17 Recently,
it has been reported that succinimides can also be synthesized by addition reactions of
amines to olefinic bond of maleimides18 in the presence of a catalyst.
However, these methods suffer from some disadvantages that involve long-reaction
time, harsh reaction conditions, and unsatisfactory yields by using high temperatures and
the hydrolysis reaction.8,17 In addition, more than one step is involved in the synthesis of
these compounds.
Therefore, the development of an efficient method for the synthesis of these com-
pounds is an active ongoing research area and there is scope for further improvement toward
milder reaction conditions and higher yields.
Over the last few years, there has been a considerable growth in interest in the use
of heteropolyacids, HPAs, in organic synthesis because of their ease of handling, enhance
reaction rates, low cost, simple work-up, and recyclability of the catalyst.19–23
In continuation of our investigation on the use of heteropolyacids as catalyst for chem-
ical synthesis,9 we wish to report a simple, convenient, and efficient method for the prepa-
ration of N-sulfonyl pyrrolidine-2,5-diones derivatives from sulfamides and succinic anhy-
dride in the presence of catalytic amounts of Dawson type heteropolyacid H6P2W18O62, as
an eco-friendly catalyst.
To the best of our knowledge, no N-sulfonyl pyrrolidine-2,5-diones derivatives have
been reported to date (Scheme 1).
RESULTS AND DISCUSSION
In our previous works, we have established that chlorosulfonyl isocyanate (CSI) is a
suitable reagent allowing the introduction a sulfonamide moiety in biomolecules.24 CSI is
also the reagent of choice for the preparation of sulfonyl pyrrolidine-2,5-diones derivatives.

NEW SUBSTITUTED N-SULFONYL PYRROLIDINE-2,5-DIONE
271
Scheme 1
In this case, CSI contains the required sulfonyl group and the nitrogen, which is necessary
for the formation of pyrrolidine-2,5-diones.
The synthetic pathway followed for the preparation of the title compounds was ac-
complished by a three-steps sequence as shown in Scheme 1. First, the alcohol, t-butanol,
reacted smoothly with chlorosulfonyl isocyanate in the presence of dichloromethane to
easily form the desired carbamate. In the second step, condensation of the carbamate with
commercially available corresponding amines (propylamine, butylamine, tert-butylamine,
aniline, benzylamine, 3-fluoroaniline, 1,2,3,4-tetrahydroisoquinoline and 1-phenyl piper-
azine) in the presence of triethylamine at 0◦C afforded substituted sulfamides (1a–h) in
good yields. These products were purified by chromatography on silica gel (eluted with
DCM/MeOH: 9.1).
In the second step (Scheme 1), the deprotection of 1a–h in water with stirring at reflux
temperature provided deprotected sulfamides (2a–h) in 80% yield.25
In the last stage of the synthesis, compounds (2a–h) were subjected to the condensa-
tion reaction in on acidic medium under solvent reflux. The condensation was attempt with
a catalytic amount of Dawson-type heteropolyacid which showed its greater reactivity in
the acylation of sulfamide, 9 yielding N-sulfonyl pyrrolidine-2, 5-diones derivatives (3a-h).
Identification of all isolated products (1a–h), (2a–h), and (3a–h) was accomplished
by 1H and 13C NMR spectroscopies and mass spectrometry.
Initially, in order to find the optimal conditions, the reaction of 3,4-
Dihydroisoquinoline-2(1H)-sulfonamide (2 g) (1 mmol) with succinic anhydride
(2mmol) in the presence of various amount of H6P2W18O62 in various solvents were
used as a model reaction. The best result has been obtained at 2 mmol% of catalyst in
acetonitrile (Entry 5, Table 1). In order to show the merit of the presented protocol, the
model reaction between 3,4-Dihydroisoquinoline-2(1H)-sulfonamide (2 g) and succinic
anhydride was described, and different catalysts such as H6P2W12Mo6 O62, H3PW12O40,
H2SO4, montmorillonite K10 were subjected to the reaction (Table 1).
It should be noted that a blank reaction without any catalyst gave no product even after
1 h under identical conditions (Entry 13, Table 1). It should be noted that, this method is

272
C. BOUGHELOUM ET AL.
Table 1 Synthesis of N-sulfonyl pyrrolidine-2,5-diones derivatives using various conditions
Entry
Solvent
Catalyst (mmol%)
Time (min)/ Conversion (%)a
1
2
3
4
5
6
7
8
9
10
11
12
13
CH2Cl2
CHCl3
THF
H6P2W18O62 (2)
H6P2W18O62 (2)
H6P2W18O62 (2)
H6P2W18O62 (2)
H6P2W18O62 (2)
H6P2W18O62 (1.5)
H6P2W18O62 (1)
H6P2W18O62 (2.5)
H6P2W12Mo6 O62 (2)
H3PW12O40 (2)
H2SO4(2)
60/58
60/62
60/67
60/75
60/90
60/85
60/73
60/90
60/84
60/45
60/30
60/15
60/00
Toluene
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
K10(2)
None
aThe conversion was determined by1H NMR analysis of the crude product.
effective for the preparation of N-sulfonyl pyrrolidine-2,5-dione derivatives from reaction of
deprotected sulfamides with succinic anhydride. The optimized methodology was applied
to the synthesis of some derivatives of N-sulfonyl pyrrolidine-2,5-diones. The results are
summarized in Table 2. In all cases, good yields of products were obtained.
Table 2 H6P2W18O62 catalyzed synthesis of N-sulfonyl pyrrolidine-2,5-dione derivatives in acetonitrile under
refluxing conditions
Entry
R
Product
Time(min)/Yield(%)
1
2
3
3a
3b
3c
60/80
60/82
60/85
4
5
6
3d
3e
3f
60/80
60/83
60/81
7
8
3g
3h
60/84
60/83

NEW SUBSTITUTED N-SULFONYL PYRROLIDINE-2,5-DIONE
273
CONCLUSION
In summary, we have developed an alternative and simple procedure for the synthesis
of N-sulfonyl pyrrolidine-2,5-diones derivatives from sulfamides and succinic anhydride
using H6P2W18O62, as an eco-friendly, inexpensive, and efficient catalyst in various condi-
tions.
The advantages of this catalytic system is mild reaction conditions, short-reaction
times, high product yields, easy preparation of the catalysts, nontoxicity of the catalysts,
simple and clean work-up of the desired products.
EXPERIMENTAL
All the chemicals were commercially available and used as received.
H6P2W18O62 was prepared according to the literature.26 Melting points were deter-
mined in open capillary tubes on Buchi B-540. Proton nuclear magnetic resonance was
determined with a 400-MHz Brucker spectrometer using CDCl3 and DMSO-d6 as solvent
and TMS as an internal standard. Chemical shifts are reported in d units (ppm). All cou-
pling constants J are reported in Hertz. Multiplicity is indicated as s (singlet), d (doublet), t
(triplet), q (quadruplet), m (multiplet), and combination of these signals. The mass spectra
were recorded on a DSQ Thermoelectron apparatus (70 eV) by chemical ionization (gaseous
ammonia) by direct introduction. Elemental analysis was performed with a Perkin-Elmer
2400 C, H, N analyzer and determined values were within the acceptable limits of the
1
calculated values. Figures S1 to S16 (Supplemental Materials) are sample H NMR, 13C
NMR, and mass spectra for selected compounds.
General Procedure For The Synthesis of N-sulfonyl
Pyrrolidine-2,5-Diones (3a–h);
Under nitrogen atmosphere, a mixture of sulfamide (1 mmol), succinic anhydride
(2 mmol), and H6P2W18O62 catalyst (2 mmol%) in acetonitrile (2 mL), was stirred at
reflux. Reaction was monitored by TLC. After completion of the reaction, the solvent
was evaporated, diluted with water (10 mL) to solubilize the catalyst, and extracted with
EtOAc (3 × 15 mL), the combined organic layers were dried over anhydrous Na2SO4,
then the solvent was evaporated in vacuum, and the crude compound was purified by flash
chromatography (Merck silica gel 60 H, CH2Cl2/MeOH, 9:1) to afford the corresponding
sulfonyl pyrrolidine-2,5-dione derivatives.
N-(propyl)-2,5-dioxopyrrolidine-1-sulfonamide (3a)
Yield: 80%, mp 134◦C, Rf = 0.82 (CH2Cl2/MeOH, 9/1), 1H NMR (CDCl3, δ ppm):
1.1 (t, J = 5.02Hz, 3H, CH3),1.69 (m, 2H, CH2), 2.67(s, 4H, 2CH2-CO); 3.32 (m, 2H,
CH2), 5.3 (t, J = 5.4Hz, 1H, NH). 13C NMR (CDCl3, δ ppm): 11.3, 22.2, 28.1, 42.7, 177.6.
MS(ESI+70em/s) : 58.04(14%), 238([M+NH4]+,100%).
Elemental anal. (%), calculated: C, 38.18; H, 5.45; N, 12.72; found: C, 38.23; H,
5.49; N, 12.68.

274
C. BOUGHELOUM ET AL.
N-(butyl)-2,5-dioxopyrrolidine-1-sulfonamide (3b)
Yield: 82%, mp 136◦C, Rf = 0.80(CH2Cl2/MeOH, 9/1), 1H NMR (CDCl3, δ ppm):
0.89 (t, J = 5.02 Hz, 3H, CH3), 1.37 (m, 2H, CH2), 1.57 (m, 2H, CH2), 2.70 (s, 4H, 2CH2-
CO), 3.07 (m, 2H, CH2-N). 13C NMR (CDCl3, δ ppm): 13.5, 19.8, 28.8, 30.9, 43.5, 179.3.
MS (ESI+ 70 eV m/z): 72.09 (10%), 235(35%), 252.10 ([M+NH4]+, 100%). Elemental
anal. (%), calculated: C, 41.02; H, 5.98; N, 11.96; found: C, 41.12; H, 5.88; N, 11.87.
N-(tert-butyl)-.5-dioxopyrrolidine-1-sulfonamide (3c)
1
Yield: 85%, mp 138◦C, Rf = 0.83(CH2Cl2/MeOH, 9/1), HNMR(CDCl3,δ ppm):
1.35(s, 9H, 3(CH3); 2.65(s, 4H, 2CH2CO). 13CNMR(CDl3, δ ppm): 28.3, 29.6; 44.9, 176.6.
Ms(ESI+ 70 eVm/s): 72.05(10%), 252.09 ([M+NH4]+, 100%).
Elemental anal. (%), calculated: C, 41.02; H, 5.98; N, 11.96; found: C, 41.08; H,
5.99; N, 11.99.
N-(phenyl)-2,5-dioxopyrrolidine-sulfonamide (3d):
Yield: 80%, mp 149◦C, Rf = 0.78(CH2Cl2/MeOH, 9/1), 1H NMR (CDCl3, δ ppm):
2.77(s, 4H, 2CH2-CO), 6.86(m, 3H, Ar-H), 7.22(m, 2H, Ar-H). 13C NMR (CDCl3, δ
ppm): 28.6,117.9; 121.1, 129.5, 139.6, 175.8. MS (ESI+ 70 eV m/z): 255.13 (15%),
272.14([M+NH4]+, 85%).
Elemental anal. (%), calculated: C, 47.24; H, 3.94; N, 11.02; found: C, 47.34; H,
3.87; N, 11.09.
N-benzyl-2.5-dioxopyrrolidine-1-sulfonamide (3e):
Yield: 83%, mp 141◦C, Rf = 0.81(CH2Cl2/MeOH, 9/1), 1H NMR (CDCl3, δ ppm):
2.10(s, 4H, 2CH2CO), 4.10(d, J = 4.02 Hz, 2H, CH2-Ph), 7.26(m, 5H, H-Ar). 13C NMR
(CDCl3, δ ppm): 28.4, 44.5, 128.2, 128.7, 129.4, 138.8, 172.4. MS (ESI+ 70 eV m/z):
105.98 (8%), 296,13([M+1]+, 15%), 286.16 ([M+NH4]+, 100%).
Elemental anal. (%), calculated: C, 49.25; H, 4.47; N, 10.45; found: C, 49.34; H,
4.39; N, 10.49.
N-(3-fluorophenyl)-2,5-dioxopyrrolidine-1-sulfonamide (3f):
Yield: 81%, mp 158◦C, Rf = 0.77(CH2Cl2/MeOH, 9/1), 1H NMR (CDCl3, δ ppm):
2.94(s, 4H, 2CH2CO), 6.94(m, 1H, H-Ar), 7.26(m, 1H, H-Ar), 7.46(m, 1H, H-Ar), 7.66(m,
1H, H-Ar). 13C NMR (CDCl3, δ ppm): 28.6, 105.6, 110.1, 114.6, 130.7, 139.4, 163.9, 173.3.
MS (ESI+ 70 eV m/z): 111.04 (10%), 175.04 (10%), 290.10 ([M+NH4]+, 100%).
Elemental anal. (%), calculated: C, 44.12; H, 3.31; N, 10.29; found: C, 44.04; H,
3.38; N, 10.19.
1-(3,4-Dihydroisoquinolin-2(1H)-yl) Sulfonyl) Pyrrolidine-2.5-dione (3g):
Yield: 84%, mp 132◦C, Rf = 0.82(CH2Cl2/MeOH, 9/1), 1H NMR (CDCl3, δ ppm):
2.67 (s, 4H, 2CH2-CO), 2.91(t, 2H, J = 5.8 Hz, CH2-ph), 3.73(t, 2H, J = 5.7 Hz, CH2N),
4.59(s, 2H, CH2N), 7.02(m, 1H, Ar-H), 7.08(m, 1H, Ar-H), 7.14(m, 2H, Ar-H). 13C NMR

NEW SUBSTITUTED N-SULFONYL PYRROLIDINE-2,5-DIONE
275
(CDCl3, δ ppm): 28.5, 28.5, 44.6, 47.4, 126.3, 126.6, 127.2, 128.9, 131.1, 133.2, 172.5. MS
(ESI+ 70 eV m/z): 102.00(17%), 132.04(31%), 156.08(17%), 219.99(27%), 229.99(43%),
295.04([M+H]+, 10%), 312.05 ([M+NH4]+, 100%).
Elemental anal. (%), calculated: C, 53.06; H, 4.76; N, 9.52; found: C, 53.12; H, 4.81;
N, 9.63.
1-((4-Phenylpiperazine-1yl)sulfonyl)pyrrolidine-2,5-dione (3h):
Yield: 83%, mp 152◦C, Rf = 0.78(CH2Cl2/MeOH, 9/1), 1H NMR (CDCl3, δ ppm):
2.77(s, 4H, 2CH2-CO), 3.21(t, 4H, CH2-N), 3.56(t, 4H, CH2-N), 6.86(m, 3H, Ar-H),
7.22(m, 2H, Ar-H). 13C NMR (CDCl3, δ ppm): 28.6, 46.4, 49.1, 117.1, 121.1, 129.4, 150.6,
172.6. MS (ESI+ 70 eV m/z): 161.20 (6%), 216.00 (6%), 241.99(7%), 324.02([M+H]+,
100%).
Elemental anal. (%), calculated: C, 52.01; H, 5.26; N, 13.00; found: C, 52.11; H,
5.33; N, 13.09.
SUPPLEMENTAL MATERIAL
Supplementary data for the article (Full experimental detail for the first two steps and
supplemental data of new compounds (3a–h).) can be accessed on the publisher’s website
at http://doi.dx.org/10.1080/10426507.2014.947413.
REFERENCES
1. (a) Katritsky, A. R.; Pozharskii, A. F. Handbook of Heterocyclic Chemistry and edition, Perg-
amon, Oxford, 2000. (b) Katritsky, A. R.; Rees, C. W.; Scriven, E. F. In Comprehensive Het-
erocyclic Chemistry, Eds. Pergamon, Oxford, 1996. (c) Joule, J. A.; Mills, K. Heterocyclic
Chemistry, Blackwell Science: Oxford, 2000.
2. (a) Hargreaves, M. K.; Pritchard, J. G.; Dave, H. R. Chem. Rev. 1970, 70, 439-469. (b) Flaih, N.;
Pham-Huy, C.; Galons, H. Tetrahedron Lett. 1999, 40, 3697-3698.
3. Groutas, W. C.; Brubaker, M. J.; Stanga, M. A.; Castrisos, J. C.; Crowley, J. P.; Schatz, E. J. J.
Med. Chem. 1989, 32, 1607-1611.
4. (a) Filho, V. C.; Correˆa, R.; Vaz, Z.; Calixto, J. B.; Nunes, R. J.; Pinheiro, T. R.; Andricopulo,
A. D.; Yunes, R. A. Il Farmaco 1998, 53, 55-57. (b) Shannon, H. E.; Eberle, E. L.; Peters, S. C.
Neuropharmacol 2005, 48, 1012-1020.
5. (a) Filho, V. C.; Queiroz, E. F.; Lima, E. O.; Pinheiro, T. R.; Nunes, R. J.; Yunes, R. A. Qu´ım.
Nova 1996, 19, 590-595. (b) Andricopulo, A. D.; Yunes, R. A.; Nunes, R.J.; Savi, A. O. S.;
Correˆa, R.; Cruz, A. B.; Filho, V. C. Qu´ım Nova 1998, 21, 573-577. (c) Zentz, F.; Valla, A.;
Guillou, R.; Labia, R.; Mathot, A. D. Il Farmaco 2002, 57, 421-426.
6. Kossakowski, J.; Jarocka, M. Il Farmaco 2001, 56, 785-589.
7. Zents, F.; Guillou, R. L.; Labia, R.; Sirot, D.; Linard, B.; Valla, A. Il Farmaco. 2004, 59, 879-886.
8. (a) Luszczki, J. J.; Kocharov, S. L.; Cruczwar, S. J. Neurosci. Res. 2009, 64, 267-269. (b) Obniska,
J.; Kaminski, K.; Skrzynska, D.; Pichor, J. Eur. J. Med. Chem. 2009, 44, 2224-2233. (c) Obniska,
J.; Rzepka, S.; Kamin´ski, K. Bioorg. Med. Chem. 2012, 20, 4872-4880. (d) Kamin´ski, K.;
Obniska, J.; Chlebek, I.; Wiklik, B.; Rzepka, S. Bioorg. Med. Chem. 2013, 21, 6821-6830.
9. Bougheloum, C.; Barbey, C.; Berredjem, M.; Messalhi, A.; Dupont, N.; J. Mol. Struct. 2013,
1041, 6-15.
10. (a) Barbey, C.; Bouasla, R.; Berredjem, M.; Dupont, N.; Retailleauc, P.; Aouf, N.; Lecouvey, M.
Tetrahedron, 2012, 68, 9125-9130. (b) Joshi, S.; Khosla, N. Bioorg. Med. Chem. Lett. 2003, 13,
3747-3751.

276
C. BOUGHELOUM ET AL.
11. Jeon, H.; Jo, N. H.; Yoo, K. H.; Choi, J.-H.; Cho, H.; Cho, J. H.; Oh, C. H. Eur. J. Med.Chem.
2007, 42, 358-364.
12. Kamal, A.; Reddy, K. S.; Ahmed, S. K.; Khan, N. A.; Sinha, R. K.; Yadav, J. S.; Arora, S. K.
Bioorg. Med. Chem. 2006, 14, 650-658.
13. Mader, M. M.; Shih, C.; Considine, E.; De Dios, A.; Grossman, C. S.; Hipskind, P.A.; Lin, H.-S.;
Lobb, K. L.; Lopez, B.; Lopez, J. E.; Martin Cabrejas, L. M.; Richett, M. E.; White, W. T.;
Cheung, Y. Y.; Huang, Z.; Reilly, J. E.; Dinn, S. R. Bioorg. Med.Chem. Lett. 2006, 15, 617-620.
14. Supuran, C. T.; Maresca, A.; Remko, M. J. Enzyme Inhib. Med. 2013, 28, 289-293.
15. Wasowski, C.; Gavernet, L.; Barrios, I. A.; Villalba, M. L.; Pastore, V.; Samaja, G.; Enrique, A.;
Bruno-Blanch, L. E.; Marder, M. Biochem. Pharmacol. 2012, 83, 253-259.
16. Supuran, C. T.; Casini, A.; Scozzafava, A. Med. Res. Rev. 2003, 23, 535-558.
17. (a) De Oliveira, K. N.; Chiaradia, L. D.; Martins, P. G. A.; Mascarello, A.; Cordeiro, M. N. S.;
et al. Med. Chem. Commun. 2011, 2, 500-504. (b) Faghihi, K.; Absalar, M.; Hajibeygi, M. Turk
J Chem. 2010, 34, 81-90. (c) Miller, C. A.; Long, L. M. J. Am. Chem. Soc. 1951, 73, 4895.
(d) Hendry, C. M. J. Am. Chem. Soc. 1958, 80, 973.
18. Patel, R.; Dholakiya, B.; Mishra, N. j. pharm Res. 2013, 6, 442-446.
19. Mizuno, N.; Misono, M., Chem. Rev. 1998, 98, 199-218.
20. Misono, M.; Acad, C. R. Sci. Paris. Ser. Iic. Chim./Chem. 2000, 3, 369-472.
21. Keggin, J. F. Nature. 1933, 131, 908-909.
22. Misono, M. Catal. Rev. Sci. Eng. 1987, 29, 269-321.
23. Kozhevnikov, I. V. Catal. Rev. Sci. Eng. 1995, 37, 311-352.
24. (a) Abdaoui, M.; Dewynter, G.; Aouf, N.; Favre, G.; More`re, A.; Montero, J. L. Bioorg. Med.
Chem. 1996, 4, 1227-1235. (b) Abdaoui, M.; Dewynter, G.; Montero, J. L. Tetrahedron Lett.
1996, 37, 5695-5698.
25. Wang, G.; Li, C.; Li, J.; Jia, X. Tetrahedron Lett. 2009, 50, 1438-1440.
26. Kozhevnikov, I. Catalysts for Fine Chemical Synthesis, vol. 2, Catalysis by Polyoxometalates,
Wiley ed., England, 2002.