Condensation of 2-pyrone with 3-aminopyrazolone. A novel synthesis of pyrazolo[3,4-b]pyridines

Article abstract of DOI:10.1081/SCC-120038500

A simple route to the preparation of new heterocyclic systems: pyrazolo [3,4-b] pyridines from the easily available 2-pyrone and 3-aminopyrazolone. The structure of the compounds and the mechanism of their formation are reported.

Full text of DOI:10.1081/SCC-120038500

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Condensation of 2‐Pyrone with 3‐Aminopyrazolone.
A Novel Synthesis of Pyrazolo[3,4‐b]pyridines
S. Fadel a , Y. Hajbi a , E. M. Rakib a , M. Khouili a , M. D. Pujol b & G. Guillaumet c
a Laboratoire de Chimie Organique et Analytique , Faculté des Sciences et Techniques ,
BP 523, 23000, Béni‐Mellal, Morocco
b Laboratori Química Farmacèutica, Facultat de Farmàcia , Universitat de Barcelona ,
Barcelona, Spain
c Institut de Chimie Organique et Analytique, Université d'Orléans , Rue de Chartres,
Orleans, France
Published online: 17 Aug 2006.
To cite this article: S. Fadel , Y. Hajbi , E. M. Rakib , M. Khouili , M. D. Pujol & G. Guillaumet (2004) Condensation
of 2‐Pyrone with 3‐Aminopyrazolone. A Novel Synthesis of Pyrazolo[3,4‐b]pyridines, Synthetic Communications: An
International Journal for Rapid Communication of Synthetic Organic Chemistry, 34:12, 2195-2204, DOI: 10.1081/
SCC-120038500
To link to this article: http://dx.doi.org/10.1081/SCC-120038500
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SYNTHETIC COMMUNICATIONSw
Vol. 34, No. 12, pp. 2195–2204, 2004
Condensation of 2-Pyrone with
3-Aminopyrazolone. A Novel Synthesis
of Pyrazolo[3,4-b]pyridines
1
2
S. Fadel,1 Y. Hajbi,1 E. M. Rakib,1, M. Khouili, M. D. Pujol,
*
and G. Guillaumet3
1
´
Laboratoire de Chimie Organique et Analytique, Faculte des
´
Sciences et Techniques, Beni-Mellal, Morocco
´ ` `
Laboratori Quımica Farmaceutica, Facultat de Farmacia,
2
Universitat de Barcelona, Barcelona, Spain
3Institut de Chimie Organique et Analytique,
´ ´
Universite d’Orleans, Orleans, France
ABSTRACT
A simple route to the preparation of new heterocyclic systems: pyrazolo
[3,4-b]pyridines from the easily available 2-pyrone and 3-aminopyrazolone.
The structure of the compounds and the mechanism of their formation are
reported.
*
Correspondence: E. M. Rakib, Laboratoire de Chimie Organique et Analytique,
´ ´
Faculte des Sciences et Techniques, BP 523, 23000 Beni-Mellal, Morocco; E-mail:
m.rakib@fstbm.ac.ma.
2195
DOI: 10.1081/SCC-120038500
0039-7911 (Print); 1532-2432 (Online)
www.dekker.com
Copyright # 2004 by Marcel Dekker, Inc.

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Key Words: Decarboxylation; Esterification; n-Butanol; Pyrones;
Pyrazolo[3,4-b]pyridines.
INTRODUCTION
Pyrazolo[3,4-b]pyridines are considered as very interesting compounds
and have received considerable attention as result of their biological activity
and structural relationship to indoles. A number of pyrazolo[3,4-b]pyridines
are under intensive development by research groups throughout the world.
Several compounds display interesting anxiolytic activity,[1,2] are potential
biologically active compounds as new inhibitors of xantine oxidases,[3] or
for treatment of erectile dysfunction.[4] Moreover, other pyrazolo[3,4-b]
pyridines have proved to be active against Gram positive and Gram negative
bacteria,[5] as cholesterol formation-inhibiting compounds,[6] or are promising
for the treatment of cataracts associated with diabetis.[7]
RESULTS AND DISCUSSION
Pyrazolo[3,4-b]pyridines have been prepared generally by cyclization
reactions starting from different heterocyclic reagent.[8–12] As a continuation
of our work on the synthesis of pyridine analogs which have potential pharma-
cological properties; we investigated the condensation of 2-pyrone with
5-aminopyrazolone. The pyrone derivatives are versatile and increasingly
used in a variety of organic syntheses, in particular in the synthesis of
new types of heterocyclic compounds. The pyrones are electrophilic and
highly reactive toward binucleophiles; their reactivity has been reported
in the literature.[13–19] We have found that the reaction of 2-pyrone with
5-aminopyrazolone constitutes a facile method for the synthesis of several
novel pyrazolo[3,4-b]pyridines. Thus, it has been found that condensation
of 3-aminopyrazolone 1 with pyrone 2 in refluxing n-butanol affords the
mixture of two isomeric pyrazolo[3,4-b]pyridines 3 and 4 (Sch. 1).
The products 3 and 4 were separated by silica gel chromatography
and their structures were assigned by 2D NMR-experiments (HMQC and
HMBC). The carbon at 157.0 ppm is assignable as the C-7a, and this carbon
shows a cross-peak with the CH2 at 3.62 ppm. Whereas the methyl group at
2.25 ppm gives a cross-peak to carbon signal at 158.9 ppm corresponding to
C-7a. The absence of CH2 signal due to the methylene protons of the pyrazole
1
1 in H NMR spectrum of the compounds 3 and 4, shows that cyclization is
carried out on C-4 carbon of the pyrazole ring.

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2197
Scheme 1.
The synthesis of the compounds 3 and 4 can be explained by the following
mechanism: initial competitive attack of the amino group on C-6 and C-4 of
pyrone 2 followed by the opening of the pyranic cycle and formation of the
intermediates [A] and [B]. Butanol (weak nucleophile) plays an important
role in this mechanism. These intermediates thus formed undergo an disrotary
electrocyclization 6ep leading after aromatization of the pyridine cycle to the
pyrazolo[3,4-b]pyridines 3 and 4 (Sch. 2).
In a classical experiment, 3-aminopyrazolone 1 reacted with pyrone 2 under
reflux in n-butanol in the presence of catalytic amount of p-toluenesulfonic
acid, giving two different compounds: pyrazolo[3,4-b]pyridines 3 and 5
(Sch. 3).
The 1H NMR spectrum of the product 5 revealed two singlets at 2.24 and
2.72 ppm corresponding to the methyl groups, and the peak at 6.54 ppm
assignable to CH group of pyridine ring.
The catalytic amount of PTSA is very important in this reaction; the
initial attack of the amino group takes place on the C-6 of the pyrone 2
giving the intermediate [A0]. The compound obtained cyclizes in two differ-
ent pathways: decarboxylation or esterification and then intramolecular
electrocyclization affording compounds 3 and 5 (Sch. 4). In the presence
of PTSA the attack was regioselectively at C-6 of the pyrone.

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Fadel et al.
Scheme 2.
In order to investigate the scope of this reaction, we studied the conden-
sation of the pyrone 2 with the 3-aminopyrazolone in acetic acid. Under these
conditions, two products were isolated: product 5 identified in the reaction with
backward flow of n-butanol with PTSA and the pyrazolo[3,4-b]pyridine 6.
The formation of 6 suggests the attack of the amino group at C-4 of the
pyrone 2 (Sch. 5).
Scheme 3.

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2199
Scheme 4.
When the acetic acid is used as a solvent, the aminopyrazolone attacks
directly the carbon on position 4 of pyrone. The intermediate [B0] evolves
according to two ways leading after aromatization to the pyrazolopyridines
5 and 6 (Sch. 6).
In conclusion, we found that the condensation of pyrone with 3-amino-
pyrazolone is dependent on the reaction conditions. Whereas in presence of
n-butanol condensation is initiated at the C-6 and C-4 carbons of pyrone 2,
in n-butanol with PTSA the aminopyrazolone attacks directly the carbon at
position 6 of pyrone, and in acetic acid, it is the C-4 position, which is
attacked, in the first step.
Scheme 5.

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Fadel et al.
Scheme 6.
EXPERIMENTAL
General Instrumentation
Melting points were determined using a Bu¨chi-Tottoli apparatus and are
uncorrected. IR spectra were recorded on a Perkin–Elmer 577 spectrometer
1
using KBr disks, only noteworthy IR absorptions are listed (cm21). H and
13C NMR spectra were recorded on a Varian Gemini 200 and 300 spectro-
meter and d values are expressed in ppm; J values are given in Hz. HMQC
and HMBC data were recorded at 400 Hz (Varian-Unity 400). Multiplicities
of 13C NMR resources were assigned by distortionless enhancement by polari-
zation transfer (DEPT) experiments. Mass spectra were recorded on a Varian
MAT 112 spectrometer MS. Elemental analysis data were taken on a Perkin–
Elmer 240C elemental analytical instrument. Column chromatography was
carried out on SiO2 (silica gel 60 Merck 0.063–0.200 mm). TLC was carried
out on SiO2 (silica gel 60, F 254 Merck 0.063–0.200 mm) and the spots
located with UV light. All solvents were dried or purified by standard
methods. All reagents were used as purchased from commercial sources.

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2201
Commercial chemicals: 3-aminopyrazolone 1 and 2-pyrone 2 were used
without purification.
Synthesis of pyrazolo[3,4-b]pyridines 3 and 4. 4-Hydroxy-6-methyl-
pyran-2-one (1.26 g, 10 mmol) was added to a solution of 3-aminopyrazolone
(5 mmol) in 50 mL of n-butanol. The reaction mixture was refluxed for 48 hr.
After evaporation of solvent, the residue was then purified over silica gel
column chromatography using a 60 : 40 mixture of hexane and ethyl acetate
as eluent.
2-(6-Methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazolo[3,4-b]pyridin-4-yl)
acetic acid butylester (3). Yield 36%, orange solid. M.p. 129–1318C; IR: 1620,
1
1730 (CO), 3010 (NH); H NMR (CDCl3): d 0.89 (t, J ¼ 7.4 Hz, 3H, CH3),
1.32 (m, 2H, CH2), 1.54 (m, 2H, CH2), 2.74 (s, 3H, CH3), 3.62 (s, 2H, CH2),
4.06 (t, J ¼ 6.6 Hz, 2H, CH2O), 6.86 (s, 1H, H-5), 7.26 (m, 1H, CH), 7.45
(m, 2H, CH), 7.86 (dd, J ¼ 0.8, 8.4 Hz, 2H, CH), 14.01 (s, 1H, NH); 13C
NMR (CDCl3): d 13.7 (CH3), 17.3 (CH3), 19.0 (CH2), 30.4 (CH2), 42.9
(CH2), 65.2 (CH2O), 109.5 (C-4), 119.5 (CH-5), 119.7, 125.3, 129.0 (5CH),
137.1 (C-10), 150.8 (C-6), 156.7 (C-3a), 157.0 (C-7a), 159.6 (CON), 169.4
(CO); MS (EI): m/z 339 (Mþ). Anal. Calcd for C19H21N3O3: C, 67.24;
H, 6.24; N, 12.38. Found: C, 67.34; H, 6.20; N, 12.44.
2-(4-Methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazolo[3,4-b]pyridin-6-yl)
acetic acid butylester (4). Yield 49%, orange solid. M.p. 114–1168C; IR:
1
1670, 1740 (CO), 2960 (NH); H NMR (CDCl3): d 0.90 (t, 3H, J ¼ 7.2 Hz,
CH3), 1.36 (m, 2H, CH2), 1.61 (m, 2H, CH2), 2.25 (s, 3H, CH3), 4.20 (s, 2H,
CH2), 4.15 (t, J ¼ 6.6 Hz, 2H, CH2O), 6.74 (s, 1H, H-5), 7.24 (m, 1H, CH),
7.42 (m, 2H, CH), 7.88 (dd, J ¼ 0.8, 8.2 Hz, 2H, CH), 14.02 (s, 1H, NH);
13C NMR (CDCl3): d 13.7 (CH3), 19.1 (CH2), 23.1 (CH3), 30.5 (CH2), 35.5
(CH2), 65.3 (CH2O), 108.3 (C-4), 117.9 (CH-5), 120.0 (2CH), 125.4 (CH),
129.0 (2CH), 137.5 (C-10), 146.4 (C-6), 155.2 (C-3a), 158.9 (C-7a), 159.7
(CON), 169.8 (CO); MS (EI): m/z 339 (Mþ). Anal. Calcd for C19H21N3O3:
C, 67.24; H, 6.24; N, 12.38. Found: C, 67.18; H, 6.28; N, 12.40.
Synthesis of pyrazolo[3,4-b]pyridines 3 and 5. To a solution of
4-hydroxy-6-methylpyran-2-one (1.26 g, 10 mmol) and 3-aminopyrazolone 2
(5 mmol) in 40 mL of n-butanol was added p-toluenesulfonic acid (0.5 mg).
The reaction mixture was refluxed for 48 hr. After evaporation of solvent,
the residue was then purified over silica gel column chromatography using
a 60 : 40 mixture of hexane and ethyl acetate as eluent. Under these conditions
the compound 3 was obtained in 40% yield.
4,6-Dimethyl-2-phenyl-1,2-dihydro-pyrazolo[3,4-b]pyridin-3-one (5).
Yield 42%, orange solid. M.p. 199–2018C; IR: 1660 (CO), 3040 (NH);
1H NMR (CDCl3): d 2.24 (s, 3H, CH3), 2.72 (s, 3H, CH3), 6.54 (s, 1H,
H-5), 7.20 (m, 1H, CH), 7.42 (m, 2H, CH), 7.94 (dd, J ¼ 1.6, 7.8 Hz, 2H,
CH), 13.81 (s, 1H, NH); 13C NMR (CDCl3): d 16.6 (CH3), 20.9 (CH3),

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Fadel et al.
108.6 (C-4), 111.8 (CH-5), 118.5 (2CH), 123.8 (1CH), 128.6 (2CH), 139.3 (C-
10), 150.1 (C-6), 153.5 (C-3a), 155.0 (C-7a), 159.1 (CON); MS (EI): m/z 239
(Mþ). Anal. Calcd for C14H13N3O: C, 70.28; H, 5.48; N, 17.56. Found: C,
70.36; H, 5.44; N, 17.50.
Synthesis of pyrazolo[3,4-b]pyridine 5 and 6. A mixture of 4-hydroxy-
6-methylpyran-2-one (126 g, 10 mmol) and 3-aminopyrazolone (5 mmol) in
acetic acid (40 mL) was heated under reflux for 30 hr. After evaporation of
the solvent, the residue was then purified over silica gel column chromato-
graphy using a 30 : 70 mixture of hexane and ethyl acetate as eluent.
Under these conditions the compound 5 was obtained in 45% yield.
2-(4-Methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazolo[3,4-b]pyridin-6-yl)
acetic acid (6). Yield 26%, white solid. M.p. 175–1778C; IR: 1690 (CO),
1
3040 (NH); H NMR (CDCl3): d 2.24 (s, 3H, CH3), 4.06 (s, 2H, CH2), 7.17
(m, 1H, CH), 7.33 (s, 1H, H-5), 7.37 (m, 2H, CH), 7.80 (dd, J ¼ 1.4,
7.6 Hz, 2H, CH), 9.38 (s, 1H, OH), 13.90 (s, 1H, NH); 13C NMR (CDCl3):
d 25.0 (CH3), 42.5 (CH2), 111.6 (C-4), 120.0 (2CH), 122.6 (CH-5), 126.2
(1CH), 130.8 (2CH), 141.3 (C-10), 151.6 (C-6), 155.2 (C-3a), 157.1 (C-7a),
160.1 (CON), 178.2 (CO); MS (EI): m/z 283 (Mþ). Anal. Calcd for
C15H13N3O3: C, 63.60; H, 4.63; N, 14.83. Found: C, 63.66; H, 4.61; N, 14.79.
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Received in Poland December 9, 2003

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