Synthesis of 3-aminoisoxazolmethylnaphthols via one-pot three-component reaction under solvent-free conditions

Article abstract of DOI:10.1007/s11164-018-3566-y

A one-pot three-component condensation reaction of 3-amino-5-methylisoxazole, aryl aldehyde and 2-naphthol to afford the corresponding 3-amino isoxazolmethylnaphthols in good to excellent yields. The remarkable features of this new procedure are high conv

Full text of DOI:10.1007/s11164-018-3566-y

Research on Chemical Intermediates
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Synthesis of 3-aminoisoxazolmethylnaphthols via one-pot
three-component reaction under solvent-free conditions
Mohyeddin Safarzaei1 Malek Taher Maghsoodlou1 Ebrahim Mollashahi1
•
•
•
Nourallah Hazeri1 Mojtaba Lashkari2
•
Received: 5 May 2018 / Accepted: 16 August 2018
Ó Springer Nature B.V. 2018
Abstract
A one-pot three-component condensation reaction of 3-amino-5-methylisoxazole,
aryl aldehyde and 2-naphthol to afford the corresponding 3-amino isoxazol-
methylnaphthols in good to excellent yields. The remarkable features of this new
procedure are high conversions, clean reaction condition, short reaction time,
nonhazardous and environmentally friendly reaction condition, inexpensive and
easily commercially availability of the catalyst and simple work-up procedures.
Keywords 3-Amino-5-methylisoxazole Á b-Naphthol Á Aryl aldehyde Á Solvent-free
conditions
Introduction
Multi-component reactions (MCRs) are an effective strategy for the synthesis of
complex structures and research into new processes can lead to the discovery of
unreported reactions. [1–4]. Since they are one-pot processes in which three or more
accessible components react to form a single product, the results of them can be
achieved in an expedient manner without isolation of any intermediate [5, 6].
Biginelli [7, 8], Betti [9], Passerini [10, 11], and Mannich [12–14] reactions are
some examples of MCRs. Nevertheless, development and discovery of new MCRs
is still in demand. Recently, this strategy became important in drug discovery in the
context of synthesis of biologically active compounds. This method increases the
efficiency of the reactions by reducing the reaction time and increases the yield of
products in comparison with normal multistep methods [15, 16]. Furthermore,
&
Malek Taher Maghsoodlou
mt_maghsoodlou@yahoo.com; mt_maghsoodlou@chem.usb.ac.ir
1
2
Department of Chemistry, Faculty of Sciences, University of Sistan and Baluchestan,
P.O. Box 98135-674, Zahedan, Iran
Faculty of Sciences, Velayat University, Iranshahr, Iran
123

M. Safarzaei et al.
isoxazole derivatives, especially 5-methylisoxazole, represent an interesting class of
heterocycles possessing a wide range of biological activity [17–22].
A large number of isoxazole derivatives exhibited antibacterial [23], antifungal
[24], anticonvulsant [25], analgesic and anticancer [26] activity (Fig. 1).
In continuation of our work on one-pot multi-component reactions (MCRs)
[27–31], we embarked on the synthesis of a novel compound possessing 2-amino-5-
methylisoxazole, aromatic aldehydes and 2-naphthol moieties embedded in a fused
molecular framework via a three-component reaction under solvent-free conditions
(Scheme 1).
Experimental section
General
Infrared (IR) spectra and melting points of all compounds were determined using an
Electrothermal 9100 apparatus and an FT-IR-JASCO-460 plus spectrometer. The 1H
and 13C NMR spectra of compounds were recorded on a Bruker DRX-300 Avance
instrument in DMSO at 300 MHz. Mass spectra were obtained on Agilent-HP and
N
NH
O
O
O
O
N
N
Pimprinine (fungicidal)
Texaline (Antitubercular)
N
O
N
HN
Amazole (Antibacterial)
Fig. 1 A few selected drugs and biologically active compounds containing an oxazole ring
Me
O
N
NH
OH
Ar
Me
O
O
OH
Oxalic acid ( 10 mol %)
Solvent-free, 90 oC
+
+
Ar
H
N
H2N
1
2
3
4
Scheme 1 Synthesis of 3-aminoisoxazolmethylnaphthols
123

Synthesis of 3-aminoisoxazolmethylnaphthols via one-pot…
Sciex-3200 Technology spectrometers operating at an ionization potential of 70 eV.
We purchased all the chemicals from chemical producers Merck and Fluka and they
were used without further purification.
General procedure for the preparation of 3-aminoisoxazolmethylnaphthols
To a mixture of aldehyde (1.0 mmol), 2-naphthol (1.0 mmol) and 3-amino-5-
methylisoxazole (1.0 mmol) oxalic acid (10 mol%) were added. The mixture was
stirred at 90 °C in an oil bath and the reaction was followed by thin layer
chromatography (TLC). After completion of the reaction, the mixture was cooled to
room temperature and washed with water to remove oxalic acid from the reaction
mixture. The solid obtained was recrystallized from absolute EtOH to furnish the
desired pure product.
Spectral data for the selected compounds
1-[(5-Methyl-isoxazol-3-ylamino)-phenyl-methyl]-naphthalen-2-ol (4a) White pow-
der, IR (KBr mmax, cm-1): 3403, 3058, 2925, 1628, 1600, 1581, 1541, 1516,
1493; H NMR (300 MHz, DMSO-d6): 2.23 (3H, s, CH3), 5.90 (1H, s, CHNH),
1
6.74–6.85 (2H, dd, Haromat), 7.14–7.41 (8H, m, Haromat), 7.76–7.83 (2H, m, Haromat),
8.01–8.04 (1H, d, NH), 10.10 (1H, s, OH); 13C NMR (75 MHz, DMSO-d6): 12.5,
53.0, 94.5, 118.9, 120.4, 122.8, 124.1, 126.4, 126.6, 128.3, 128.9, 129.0, 129.5,
132.6, 143.6, 153.2, 165.0, 167.7; MS m/z (%):77.1 (5), 98.1 (7), 115.2 (8), 202.2
(23), 215.2 (8), 231.2 (100), 246.2 (4), 330.2 (M?, 3).
1-[(5-Methyl-isoxazol-3-ylamino)-p-tolyl-methyl]-naphthalen-2-ol (4b) White pow-
der, IR (KBr mmax, cm-1): 3393, 3060, 1625, 1581, 1538, 1535, 1511, 1478,
1437; H NMR (300 MHz, DMSO-d6): 2.22, 2.24 (6H, s, 2CH3), 5.88 (1H, s,
1
CHNH), 6.67–6.80 (2H, dd, Haromat), 7.05–7.08 (2H, d, Haromat), 7.19–7.29 (4H, m,
H
aromat), 7.34–7.39 (1H, t, Haromat), 7.74–7.82 (2H, m, Haromat), 7.99–8.02 (1H, d,
NH), 10.06 (1H, s, OH); 13C NMR (75 MHz, DMSO-d6): 12.5, 21.0, 52.9, 94.4,
118.9, 120.5, 122.7, 124.2, 126.6, 128.9, 129.0, 129.4, 132.6, 135.3, 140.6, 153.1,
164.9, 167.7. MS m/z (%): 98.2 (10), 115.5 (8), 202.2 (20), 216.2 (9), 231.2 (100),
245.2 (46), 344.3 (M?, 2).
1-[(4-Methoxy-phenyl)-(5-methyl-isoxazol-3-ylamino)-methyl]-naphthalen-2-ol
(4c)
White powder, IR (KBr mmax, cm-1): 3380, 2962, 1626, 1579, 1556, 1509, 1475,
1436; 1H NMR (300 MHz, DMSO-d6): 2.21 (3H, s, CH3), 3.69 (3H, s, OCH3), 5.86
(1H, s, CHNH), 6.62–6.64 (1H, d, Haromat), 6.76–6.85 (3H, m, Haromat), 7.20–7.39
(4H, m, Haromat), 7.73–7.81 (2H, m, Haromat), 7.99–8.02 (1H, d, NH), 10.06 (1H, s,
OH); 13C NMR (75 MHz, DMSO-d6): 12.5, 52.7, 55.4, 94.4, 113.8, 118.9, 120.4,
122.7, 124.1, 126.5, 127.8, 128.9, 129.0, 129.4, 132.6, 135.4, 153.1, 158.0, 164.9,
167.7; MS m/z (%): 98.2 (20), 115.2(5), 165.2(10), 189.2 (45), 202.2 (10), 218.2
(30), 231.2 (95), 261.1 (100), 360.3 (M?, 2).
1-[(4-Chloro-phenyl)-(5-methyl-isoxazol-3-ylamino)-methyl]-naphthalen-2-ol
(4d)
White powder, IR (KBr mmax, cm-1): 3389, 3064, 1624, 1580, 1572, 1532, 1516,
123

M. Safarzaei et al.
1
1488; H NMR (300 MHz, DMSO-d6): 2.23 (3H, s, CH3), 5.88 (1H, s, CHNH),
6.69–6.87 (2H, dd, Haromat), 7.25–7.42 (7H, m, Haromat), 7.77–7.83 (2H, t, Haromat),
7.95–7.98 (1H, d, NH), 10.16 (1H, s, OH); 13C NMR (75 MHz, DMSO-d6): 12.5,
52.5, 94.4, 118.8, 119.9, 122.9, 124.0, 126.8, 128.3, 128.5, 129.0, 129.8, 130.9,
132.5, 142.8, 153.2, 164.9, 167.8; MS m/z (%): 98.2 (8), 115.2 (9), 202.2 (32), 231.2
(100), 265.1 (58), 364.2 (M?, 1).
1-[(3-Chloro-phenyl)-(5-methyl-isoxazol-3-ylamino)-methyl]-naphthalen-2-ol
(4e)
White powder, IR (KBr mmax, cm-1): 3414, 3066, 1629, 1592, 1551, 1537, 1516,
1473, 1437; 1H NMR (300 MHz, DMSO-d6): 2.23 (3H, s, CH3), 5.88 (1H, s,
CHNH), 6.70–6.91 (2H, dd, Haromat), 7.19–7.34 (6H, m, Haromat), 7.39–7.44 (1H, t,
H
aromat), 7.78–7.84 (1H, t, Haromat), 7.97–8.00 (1H, d, NH), 10.16 (1H, s, OH); 13C
NMR (75 MHz, DMSO-d6): 12.5, 52.6, 94.4, 118.8, 119.8, 122.9, 123.8, 125.4,
126.3, 126.4, 126.9, 129.0, 129.0, 129.9, 130.3, 132.4, 133.2, 146.5, 153.2, 164.8,
167.9; MS m/z (%): 98.2 (10), 115.2 (13), 202.2 (32), 231.2 (100), 265.1 (48), 364.2
(M?, 3).
1-[(2-2.3.6.1-[(3-Chloro-phenyl)-(5-methyl-isoxazol-3-ylamino)-methyl]-naphthalen-2-ol
(4f) White powder, IR (KBr mmax, cm-1): 3411, 3057, 2924, 1629, 1583, 1544,
1515, 1468, 1438; 1H NMR (300 MHz, DMSO-d6): 2.22 (3H, s, CH3), 5.78 (1H, s,
CHNH), 6.72–6.89 (2H, dd, Haromat), 7.16–7.42 (6H, m, Haromat), 7.69–7.82 (2H, m,
H
aromat), 8.04–8.07 (1H, d, NH), 9.94 (1H, s, OH); 13C NMR (75 MHz, DMSO-d6):
12.5, 52.5, 94.4, 118.6, 120.0, 122.9, 123.6, 125.4, 126.5, 126.4, 126.9, 129.2,
129.5, 129.9, 130.3, 132.4, 134.2, 146.5, 154.2, 163.6, 168.2; MS m/z (%): 98.2 (5),
115.2 (7), 202.2 (20), 231.2 (100), 265.1 (8), 364.2 (M?, 1).
1-[(4-Bromo-phenyl)-(5-methyl-isoxazol-3-ylamino)-methyl]-naphthalen-2-ol
(4 g)
White powder, IR (KBr mmax, cm-1): 3391, 3064, 1624, 1580, 1533, 1516, 1486,
1436. H NMR (300 MHz, DMSO-d6): 2.23 (3H, s, CH3), 5.88 (1H, s, CHNH),
1
6.67–6.87 (2H,dd, Haromat), 7.23–7.48 (7H, m, Haromat), 7.77–7.83 (2H,t, Haromat),
7.95–7.98 (1H, d, NH), 10.16 (1H, s, OH); 13C NMR (75 MHz, DMSO-d6): 12.5,
52.6, 94.4, 118.8, 119.4, 119.9, 122.9, 124.0, 126.8, 128.9, 129.0, 129.8, 131.2,
132.9, 143.3, 153.2, 164.9, 167.8; MS m/z (%): 98.2 (8), 101.2 (9), 115.3 (9), 202.2
(35), 215.2 (4), 231.2 (100), 311.2 (23), 408.2 (M?, 1).
1-[(3-Bromo-phenyl)-(5-methyl-isoxazol-3-ylamino)-methyl]-naphthalen-2-ol
(4h)
White powder, IR (KBr mmax, cm-1): 3417, 3065, 1629, 1586, 1555, 1516, 1504,
1474, 1437; 1H NMR (300 MHz, DMSO-d6): 2.23 (3H, s, CH3), 5.88 (1H, s,
CHNH), 6.70–6.91 (2H, dd, Haromat), 7.19–7.49 (7H, m, Haromat), 7.78–7.84 (2H, t,
H
aromat), 7.98–8.00 (1H, d, NH), 10.14 (1H, s, OH); 13C NMR (75 MHz, DMSO-
d6): 12.5, 52.6, 94.4, 118.8, 119.8, 121.9, 122.9, 123.8, 125.8, 126.9, 129.0, 129.0,
129.1, 129.3, 129.9, 130.6, 132.4, 146.7, 153.2, 164.8, 167.9; MS m/z (%): 98.2
(10), 101.2 (9), 115.3 (12), 202.2 (32), 231.2 (100), 311.1 (25), 408.2 (M?, 1).
1-[(4-Fluoro-phenyl)-(5-methyl-isoxazol-3-ylamino)-methyl]-naphthalen-2-ol
(4i)
White powder, IR (KBr mmax, cm-1): 3400, 3061, 1626, 1604, 1582, 1539,1507,
1470, 1437; 1H NMR (300 MHz, DMSO-d6): 2.23 (3H, s, CH3), 5.87 (1H, s,
123

Synthesis of 3-aminoisoxazolmethylnaphthols via one-pot…
CHNH), 6.68–6.86 (2H, dd, Haromat), 7.06–7012 (2H, t, Haromat), 7.25–7.33 (4H, m,
H
aromat), 7.36–7.41 (1H, t, Haromat), 7.76–7.83 (2H, m, Haromat), 7.97–7.99 (1H, d,
NH), 10.11 (1H, s, OH); 13C NMR (75 MHz, DMSO-d6): 12.5, 52.5, 94.4, 114.9,
115.1, 118.8, 120.1, 122.8, 124.0, 126.7, 128.4, 128.5, 129.0, 129.7, 132.5, 139.7,
139.7, 153.1, 159.5, 162.7, 164.9, 167.8; MS m/z (%): 98.2 (10), 115.2 (8), 202.2
(8), 220.2 (21), 249.2 (100), 348.3 (M?, 1).
1-[(5-Methyl-isoxazol-3-ylamino)-(4-nitro-phenyl)-methyl]-naphthalen-2-ol (4j) Yel-
low powder, IR (KBr mmax, cm-1): 3416, 3082, 1628, 1604, 1595, 1582, 1541,
1514, 1488; 1H NMR (300 MHz, DMSO-d6): 2.25 (3H, s, CH3), 5.89 (1H, s,
CHNH), 6.79–7.00 (2H, dd, Haromat), 7.26–7.30 (2H, m, Haromat), 7.38–7.43 (1H, t,
H
aromat), 7.52–7.55 (2H, d, Haromat), 7.80–7.85 (2H, m, Haromat), 7.93–7.96 (1H, d,
NH), 8.15–8.18 (2H, d, Haromat), 10.25 (1H, s, OH); 13C NMR (75 MHz, DMSO-
d6): 12.5, 52.9, 94.4, 96.3, 118.4, 118.8, 119.4, 123.0, 123.6, 123.8, 124.4, 127.0,
127.7, 127.8, 128.9, 129.0, 129.1, 130.0, 130.2, 132.4, 146.3, 152.2, 153.3, 164.8,
168.0, 169.8; MS m/z (%): 43.2 (17), 115.2 (50), 144.2 (60), 202.2 (39), 230.2 (100),
2454.2 (32), 291.2 (52), 375.3 (M?, 1).
1-[(5-Methylisoxazol-3-ylamino)-(pyridin-4-yl)-methyl]-naphthalen-2-ol (4k) White
powder, IR (KBr mmax, cm-1): 3375, 3140, 2924, 1629, 1604, 1576, 1560, 1512;
1H NMR (300 MHz, DMSO-d6): 2.24 (3H, s, CH3), 5.89 (1H, s, CHNH), 6.70–6.93
(2H, dd, Haromat), 7.25–7.30 (4H, m, Haromat), 7.38–7.43 (1H, t, Haromat), 7.79–7.84
(2H, t, Haromat), 7.92–7.95 (1H, d, NH), 8.44–8.46 (2H, d, Haromat), 10.2 (1H, s, OH);
13C NMR (75 MHz, DMSO-d6): 12.5, 52.3, 94.4, 118.8, 119.2, 121.9, 122.9, 123.8,
126.9, 129.0, 129.0, 130.1, 132.4, 149.6, 153.0, 153.4, 164.8, 168.0; MS m/z (%):
83.0 (9), 121.0 (9), 188.0 (13), 234.0 (15), 256.0 (30), 304.2 (20), 332.1 (100), 333.1
(14), 334.1 (M?? H, 3).
1-[(5-Methylisoxazol-3-ylamino)-(thiophen-2-yl)methyl]-naphthalen-2-ol (4l) White
1
powder, IR (KBr mmax, cm-1): 3394, 3113, 1624, 1582, 1537, 1530, 1516; H
NMR (300 MHz, DMSO-d6): 2.21 (3H, s, CH3), 5.90 (1H, s, CHNH), 6.79–6.80
(1H, d, Haromat), 6.89–6.91 (2H, t, Haromat), 6.97 (1H, d, Haromat), 7.25–7.33 (3H, m,
H
aromat), 7.40–7.45 (1H, t, Haromat), 7.77–7.84 (2H, m, Haromat),8.09–8.12 (1H, d,
NH), 10.2 (1H, s, OH); 13C NMR (75 MHz, DMSO-d6): 12.5, 50.5, 94.4, 118.9,
119.6, 122.9, 123.7, 124.3, 124.7, 126.7, 126.9, 128.9, 129.0, 129.8, 132.5,148.2,
153.3, 164.5, 168.0; MS m/z (%):59.0 (3), 96.9 (100), 118.9 (10), 224.0 (11), 236.9
(7), 235.0 (M?–H, 96).
Results and discussion
We compared the catalytic activity of oxalic acid with some other catalysts reported
in the literature for the three-component condensation reaction of benzaldehyde,
2-naphthol and 3-amino-5-methylisoxazole in solvent-free conditions after 40 min
at 80 °C (Table 1). In the absence of the catalyst, no product was formed (Table 1,
entry 1). After several experiments, oxalic acid was found to the most efficient
catalyst among all the other examined catalysts under these conditions.
123

M. Safarzaei et al.
To achieve an optimal temperature, solvent and amounts of catalyst, we used
different solvents such as ethanol, tetrahydrofuran (THF), dimethylformamide
(DMF), AcOH:H2O(1:1) and chloroform in 70 °C, but no superior results were
obtained as compared to solvent-free condition (Table 2, entries 1–8). Also, we
studied the influence of temperature on the reaction time and percentage yield.
Table 2 displays that 90 °C was optimum temperature for maximum conversion.
Increasing the temperature above 90 °C neither improved the yield nor decreased
the reaction time (Table 2, entries 9–13). In contrast, reducing the temperature is
Table 1 Effects of catalyst on the synthesis of 3-aminoisoxazolmethylnaphthols
Entry
Catalyst (10 mol%)
Yield (%)a
1
2
3
4
5
6
7
8
Trace
30
–
Fe2O3
MgSO4Á3H2O
ZnCl2
72
75
K2HPO4
65
CoCl2Á6H2O
Oxalic acid
NaOAc
60
86
76
aIsolated yields
Table 2 Optimization of solvent, temperature and catalyst in synthesis of compound 4a
Entry
Solvent
Temperature (°C)
Catalyst (mol%)
Time (min)
Yield (%)a
1
EtOH
70
70
70
70
70
70
70
70
r.t
10
10
10
10
10
10
10
10
10
10
10
10
10
3
30
30
35
45
40
45
40
25
60
45
8
55
60
66
53
40
50
55
81
Trace
57
92
90
90
85
90
88
2
H2O: EtOH(1:1)
3
AcOH:H2O(1:1)
4
AcOH
5
DMF
6
THF
7
CHCl3
8
–
–
–
–
–
–
–
–
–
9
10
11
12
13
14
15
16
50
90
100
110
90
90
90
10
10
20
15
22
5
15
aIsolated yields. The bolded entry indicates the largest yield obtained.
123

Synthesis of 3-aminoisoxazolmethylnaphthols via one-pot…
Table 3 Synthesis of 3-aminoisoxazolmethylnaphthols using oxalic acid in solvent-free conditions
Entry
Product
Time (min)
Isolated yield (%)a
Product
M.p (°C)
Me
O
N
1
8
92
4a
212–214
NH
OH
Me
O
N
2
12
90
4b
202–203
194–195
NH
OH
Me
O
N
H3CO
3
16
88
4c
NH
OH
Me
O
N
Cl
4
5
6
6
10
8
93
91
92
4d
4e
4f
194–195
NH
OH
Me
O
N
Cl
193–195
NH
OH
Me
Cl
O
N
185–186
NH
OH
123

M. Safarzaei et al.
Table 3 continued
Entry
Product
Me
Time (min)
10
Isolated yield (%)a
Product
M.p (°C)
200–201
O
N
Br
7
92
4g
NH
OH
Me
O
Br
N
8
12
90
94
91
91
92
4h
195–196
193–194
150–151
200–202
185–187
NH
OH
Me
O
N
F
9
8
4i
NH
OH
Me
O
N
O2N
10
11
12
10
12
10
4j
4k
4l
NH
OH
Me
O
N
N
NH
OH
Me
O
N
NH
OH
S
aYields refer to those of pure isolated products characterized by IR, 1H and 13C NMR spectroscopic data
and mass spectrometry
123

Synthesis of 3-aminoisoxazolmethylnaphthols via one-pot…
O
C
O
C
H
O
O
H
O
C
O
C
A
H
O
Ar
H
OH
Ar
O
H
O
O
O
O
O
H
Ar
H
Ar
H
B
1
2
C
o-QMs
Me
O
N
Ar
Ar
NH
OH
H2N
N
O
Oxalic acid
O
+
Me
o-QMs
3
4
Scheme 2
3-aminoisoxazolmethylnaphthols (4a–k)
A
suggested
mechanism
for
the
three-component
synthesis
of
detrimental to the reaction, resulting in lower yields. We also studied the model
reaction catalyzed by oxalic acid with different catalyst loading (Table 2, entries
14–16). The optimal quantity of catalyst was found to be 10 mol%. Excess amount
of catalyst did not increase the yields.
The reactions of 2-naphthol with various aromatic aldehydes and 3-amino-5-
methylisoxazole were carried out in the presence of 10 mol% oxalic acid at 90 °C.
The results are summarized in Table 3 and showed an excellent tolerance toward
electron-withdrawing and electron-donating groups with similar yields and reaction
times. However, aromatic aldehydes containing electron-withdrawing groups gave
shorter times and higher yields than that with electron-donating groups. A suggested
mechanism for this transformation is shown in Scheme 2. According to the
literature [28, 32, 33], it is suggested that the reaction is performed through o-QMs.
All the products 4a–l are new compounds identified by IR, 1H NMR, 13C NMR and
MS spectral data.
Conclusion
In this research, we have demonstrated a green and efficient method for the
synthesis of 3-aminoisoxazolmethylnaphthols via condensation of an aldehyde,
2-naphthol and 3-amino-5-methylisoxazole using oxalic acid as the catalyst in
solvent-free conditions. The catalyst is green, inexpensive and readily commercially
available. Simple experimental procedure, excellent yields, shorter reaction time,
easy workup, product purity, a nonhazardous nature and environmentally friendly
reaction conditions are the key features of this procedure.
Acknowledgements We gratefully acknowledge financial support from the Research Council of the
University of Sistan and Baluchestan.
123

M. Safarzaei et al.
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