Design and identification of nano-Mg-[4-methoxy phenyl-salicylaldimine–methyl-pyranopyrzole] Cl2 and its catalytic application on the preparation of 1-(α-aminoalkyl)-2-naphthols

Article abstract of DOI:10.1002/aoc.5372

Nano-Mg- [4-methoxy phenylsalicylaldiminemethylpyranopyrazole]Cl₂ (nano-[Mg-4MSMP]Cl₂) as a nano-Schiff base complex was prepared and fully characterized using some various techniques including fourier transform infrared spectroscopy

Full text of DOI:10.1002/aoc.5372

Received: 14 August 2019
DOI: 10.1002/aoc.5372
Revised: 26 September 2019
Accepted: 21 October 2019
F U L L P A P E R
Design and identification of nano-Mg-[4-methoxy phenyl-
salicylaldimine–methyl-pyranopyrzole] Cl2 and its catalytic
application on the preparation of 1-(α-aminoalkyl)-2-
naphthols
Hamid Goudarziafshar
| Ahmad Reza Moosavi-Zare
| Jafar Hasani
Sayyed Jamaleddin Asadabadi University,
Asadabad, 6541861841, I. R, Iran
Nano-Mg- [4-methoxy phenylsalicylaldiminemethylpyranopyrazole]Cl2 (nano-
[Mg-4MSMP]Cl2) as a nano-Schiff base complex was prepared and fully
characterized using some various techniques including fourier transform
infrared spectroscopy (FT-IR), energy-dispersive x-ray spectroscopy (EDS),
X-ray diffraction (XRD), thermal gravimetric analysis (TGA), differential ther-
mal gravimetric analysis (DTA), mass spectroscopy (MS) and scanning electron
microscopy (SEM). Nano-[Mg-4MSMP]Cl2 was successfully used as an efficient
catalyst for the preparation of some 1-(α-aminoalkyl) -2 -naphthols.
Correspondence
Ahmad Reza Moosavi-Zare, Sayyed
Jamaleddin Asadabadi University,
Asadabad, 6541861841, I. R. Iran.
Email: moosavizare@yahoo.com
Hamid Goudarziafshar, Sayyed
Jamaleddin Asadabadi University,
Asadabad, 6541861841, I. R. Iran.
Email: hamid_gafshar@yahoo.com
K E Y W O R D S
1-(α-aminoalkyl)-2-naphthol, Nano-[mg-4MSMP]Cl2, Pyranopyrazole, Schiff base
Funding information
Sayyed Jamaleddin Asadabadi University
1 | INTRODUCTION
carbonyl compounds such as aldehydes or ketones.
Schiff base compounds are widely introduced as one of
One-pot multi-component reactions are important in
organic chemistry because of the ability of them to pre-
pare the related products from the reaction between three
or more starting materials in one step without the crea-
tion of side products and atomic waste. Short reaction
time, high efficiency, simplicity, easy work up and the
lack of the need to isolate the generated intermediates
during the reaction are significant advantages of these
reactions.[1–11]
1-aminoalkyl-2-naphthols could be hydrolyzed and
converted to 1-amidoalkyl-2-naphthols as a significant
class of bioactive compounds. Hypotensive and bradycar-
dia properties have been reported for 1-amidoalkyl-
2-naphthols.[12–15] One of the important methods for the
direct preparation of these considerable compounds is
the one-pot three-component reaction of aldehyde,
2-naphthol and amine derivatives.[16–24]
the useful kinds of ligands due to their easy and
convenient route for the preparation of materials and
their interesting coordination chemistry.[25] Schiff base
complexes were prepared by the coordination of Schiff
base ligands with metal. There are some important
activities for these compounds such as antibacterial,
antifungal, anticancer, antioxidant, anti-inflammatory,
antimalarial, antiviral properties. Additionally, Schiff
base complexes were used as efficient catalysts in
organic transformations.[26–28] In continuing our
previous works to prepare some new Schiff base
complexes by the reaction of pyranopyrazole deriva-
tives with salicylaldehyde and different metal
salts,[29–33] herein, we have designed and identified
nano-Mg-[4-methoxy
phenylsalicylaldiminemethylpy-
ranopyrazole]Cl2 (nano-[Mg-4MSMP]Cl2) (Figure 1)
and used it, as an active and efficient catalyst, for the
preparation of 1-(α-aminoalkyl)-2-naphthol derivatives
(Scheme 1).
Azomethine compounds, namely Schiff bases are
prepared by the reaction of primary amine with
Appl Organometal Chem. 2020;e5372.
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https://doi.org/10.1002/aoc.5372

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GOUDARZIAFSHAR ET AL.
for three times to purify nano-[Mg-4MSMP]Cl2 from
excess salicylaldehyde (Scheme 2).
(E)-6-((2-hydroxybenzylidene) amino)-4-(4-methoxy-
phenyl)-3-methyl-1,4- dihydropyrano [2,3-c] pyrazole-
5-carbonitrile.
Pale yellow solid; M.P: 254–256 C; IR (KBr, cm−1):
ꢀ
3631, 3310, 3129, 3048, 2967, 2841, 2207, 1630, 1599,
1
1561, 1513, 759; H NMR (400 MHz, DMSO-d6) δ 12.39
(s, 1H), 11.72 (s, 1H), 9.26 (d, J = 1.70 Hz, 1H), 7.93–7.86
(m, 1H), 7.57–7.50 (m, 1H), 7.25 (d, J = 8.70 Hz, 2H), 7.04
(t, J = 7.50 Hz, 2H), 6.95 (d, J = 8.70 Hz, 2H), 5.00 (s,
1H), 3.77 (s, 3H), 1.85 (s, 3H). 13C NMR (100 MHz,
DMSO-d6): δ (ppm) 10.2, 37.4, 55.5, 88.8, 97.4, 114.5,
117.4, 118.2, 119.6, 120.2, 129.5, 132.7, 134.6, 135.9, 136.6,
155.0, 157.9, 158.9, 161.06, 163.1.
FIGURE 1 The proposed structures of nano-[Mg-4MSMP]Cl2
2 | EXPERIMENTAL
All chemicals were purchased from Merck or Fluka
Chemical Companies. The known products were identi-
fied by comparison of their melting points and spectral
data with those reported in the literature.
2.2 | General procedure for the synthesis
of 1-(α-aminoalkyl)-2-naphthol derivatives
2.1 | Procedure for the synthesis of
nano-mg- [4-methoxy phenyl salicyl
aldimine methyl pyrano pyrazole] Cl2
(nano-[mg-4MSMP]Cl2)
A mixture of 2-naphthol (0.288 g, 2 mmol), amine
(2.5 mmol), aromatic aldehyde (2 mmol), nano-[Mg-
4MSMP]Cl2 (10 mol %) and ethanol (10 ml) was added to
a 25 ml round-bottomed flask connected to a reflux con-
denser and stirred at 65 ꢀC for appropriate time. After the
completion of the reaction, as monitored by TLC, the
reaction mixture was cooled to room temperature and
the product and remind starting materials were extracted
A mixture of ethyl acetoacetate (0.13 g, 1 mmol), hydra-
zine hydrate (1.25 mmol) and isonicotinic acid (0.1 mmol,
0.0123 g, 10 mol%) was added in a 10 ml round-bottomed
flasꢀk connected to a reflux condenser, and stirred at
85 C for 5 min and then 4-anisaldehyde (1 mmol) and
malononitrile (0.066 g, 1 mmol) were added to the reac-
tion mixture. After the completion of the reaction, as
followed by TLC, the reaction mixture was cooled to
room temperature. Water was added to the reaction
mixture to dissolve isonicotinic acid and then aqueous
layer was separated from the reaction mixture.
Afterwards, the solid residue (crude product) was
triturated by a mixture of ethanol and water (9/1) to
prepare (E)-6-(2-hydroxybenzylideneamino)-4-(4-metho-
xyphenyl)-3-methyl-1,4-dihydropyrano[2,3-c] pyrazole-
5-carbonitrile as an amine.[34] The prepared amine
(1 mmol) and MgCl2.6H2O (1 mmol) were pulverized in a
mortar for 10 min and then, transferred to a 25 ml
round-bottomed
flask containing
salicylaldehyde
(1.5 mmol) and ethanol (10 ml), connected to a reflux
condenser and stirred under reflux condition for 72 hr.
Finally, the reaction mixture was washed by ethyl acetate
SCHEME 2 The preparation of nano-[Mg-4MSMP]Cl2
SCHEME 1 The preparation of 1-(α-aminoalkyl)-
2-naphthols catalyzed by nano-[Mg-4MSMP]Cl2

PREPARATION OF 1-(α-AMINOALKYL)-2-NAPHTHOLS
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with warm ethanol (20 ml) to separate from the catalyst
by filtration (the product and remind starting materials
are soluble in warm ethanol; however, the catalyst is not
soluble in this solvent). The product was purified by the
recrystallization of the reaction mixture in ethanol (90%).
The spectral data of products were given in Supporting
Information.
1H), 7.27 (t, J = 7.50 Hz, 1H), 7.45 (t, J = 7.70 Hz,
1H),7.64 (t, J = 8.00 Hz, 1H), 7.77 (dd, J = 8.50, 4.60 Hz,
2H), 8.36–8.02 (m, 3H), 8.55 (s, 1H), 12.92 (s, 1H); 13C
NMR (100 MHz, DMSO-d6); δ 52.3, 66.5, 68.7, 119.9,
122.0, 123.2, 123.6, 127.2, 128.7, 129.2, 130.33, 130.7,
132.4, 135.7, 142.3, 148.5, 151.0, 154.9, 115.6.
1-((4-(benzyloxy) phenyl) (morpholino) methyl)
naphthalen-2-ol (5).
1-((4-chlorophenyl) (piperidin-1-yl) methyl) naphtha-
len-2-ol (1).
White crystalline solid; M.P:198–200 ꢀC; IR (KBr,
[18]
White solid; M.P:164–166 C; lit.
M.P.:165–166 C;
cm−1): 3433, 3057, 3035, 2974, 2895, 2857, 2818, 2771,
ꢀ
ꢀ
IR (KBr, cm−1): 3453, 3059, 3019, 2973, 2852, 2822, 1598,
1622, 1607, 1583, 1511, 1468, 1454, 1235, 1119, 748; H
1
1
1622, 1451, 1115, 827; H-NMR (250 MHz, DMSO-d6): δ
NMR (400 MHz, DMSO-d6) δ (ppm) 2.47–2.28 (m, 2H),
2.71–2.55 (m, 2H), 3.67 (s, 4H), 5.02 (s, 2H), 5.34 (d,
J = 2.90 Hz, 1H), 6.99–6.91 (m, 2H), 7.10 (dd, J = 8.80,
2.00 Hz, 1H), 7.47–7.20 (m, 7H), 7.55 (d, J = 8.20 Hz,
2H), 7.73 (dd, J = 8.80, 1.40 Hz, 1H), 7.77 (m, 1H), 8.04
(s, 1H), 13.24 (s, 1H); 13C NMR (100 MHz, DMSO-d6) δ
(ppm) 52.3, 66.61, 69.6, 69.7, 115.3, 116.4, 119.9, 122.0,
122.9, 126.9, 128.1, 128.3, 128.72, 128.8, 129.0, 129.6,
131.8, 132.4, 137.3, 154.5, 154.8, 158.4.
(ppm) 1.92–0.99 (m, 6H), 2.32 (s, 2H), 3.15–2.49 (m, 2H),
5.30 (s, 1H), 7.06 (d, J = 8.9 Hz, 1H), 7.20 (t, J = 7.40 Hz,
1H), 7.31 (s, 1H), 7.36 (dd, J = 5.70, 3.80 Hz, 2H), 7.60 (d,
J = 8.00 Hz, 2H), 7.70 (t, J = 8.80 Hz, 2H), 7.97 (d,
J = 8.60 Hz, 1H), 13.69 (s, 1H); 13C NMR (62.5 MHz,
DMSO-d6): δ (ppm); 24.0, 26.0, 52.7, 69.6, 116.5, 121.7,
120.0, 122.8, 126.9, 128.5, 129.0, 129.1, 129.6, 130.8, 132.3,
132.7, 139.5, 155.4.
1-((4-methoxyphenyl) (morpholino) methyl) naphtha-
len-2-ol (2).
4-((2, 5-dimethoxyphenyl) (naphthalen-1-yl) methyl)
morpholine (13).
White crystalline solid; M.P.:125–127 ꢀC; lit.[19] M.
P:125–126 ꢀC; IR (KBr, cm−1): 3452, 3064, 3042, 2969,
2961, 2828, 1621, 1600, 1582, 1513, 1360, 1239, 1119,
942, 877; 1H NMR (400 MHz, DMSO-d6): δ (ppm)
2.46–2.28 (m, 2H), 2.57 (s, 2H), 3.69 (s,7H), 5.43 (d,
J = 3.10 Hz, 1H), 6.88 (d, J = 8.30 Hz, 2H), 7.06 (m,1H),
7.27 (d, J = 7.60 Hz, 1H), 7.48–7.35 (m, 1H), 7.54 (d,
J = 8.20 Hz, 2H), 7.75 (m,2H), 8.04 (s,1H), 13.26 (s,1H);
13C NMR (100 MHz, DMSO-d6): δ (ppm) 52.4, 55.4, 66.6,
69.8, 114.5, 116.4, 119.9, 122.0, 122.9, 126.9, 128.7, 129.0,
129.6, 130.4, 131.6, 132.4, 154.8, 159.2.
White crystalline solid; M.P: 145-147 ꢀC; IR (KBr,
cm−1); 3054, 3003, 2960, 2915, 2857, 2836, 2761, 2691,
1621, 1600, 1502, 1464, 1454, 1416, 1341, 1301, 1222,
1
1118, 946, 827, 755; H NMR (250 MHz, DMSO-d6) δ
13.27 (s, 1H), 7.89–7.63 (m, 3H), 7.35 (t, J = 7.60 Hz, 1H),
7.20 (t, J = 7.40 Hz, 1H), 7.11 (d, J = 8.80 Hz, 1H), 7.00
1-((4-bromophenyl) (morpholino)methyl) naphthale
n-2-ol (3).
[19]
ꢀ
White crystalline solid; M.P:179–180 C; lit.
M.P.:
180–182 ꢀC; IR (KBr, cm−1): 3456, 3055, 2961, 2920, 2896,
2854, 2822, 2778, 2686, 1620, 1599, 1532, 1519, 1487,
1
1469, 1072, 837, 521; H NMR (400 MHz, DMSO-d6) δ
(ppm) 2.87 (m, 4H), 3.67 (m, 4H), 5.44 (d, J = 2.90 Hz,
1H), 7.11 (q, J = 8.20 Hz, 1H), 7.31–7.23 (m, 1H), 7.42 (m,
1H), 7.53 (d, J = 8.10 Hz, 2H), 7.61 (d, J = 8.20 Hz, 2H),
7.76 (m, 2H), 8.09 (s, 1H), 13.06 (s, 1H), 13C NMR
(100 MHz, DMSO-d6); δ (ppm) 52.3, 66.5, 69.3, 115.8,
119.9, 121.54, 121.9, 123.1, 127.0, 128.7, 129.1, 129.9,
131.2, 132.1, 132.4, 139.4, 154.8.
1-(morpholino(3-nitrophenyl)methyl)naphthalen-2-ol
(4).
Light yellow crystalline solid; M.P:173–175 ꢀC; IR
(KBr, cm−1): 3433, 3058, 2963, 2886, 2851, 2692, 1622,
1
1600, 1530, 1585, 1451, 1418, 1349, 1018, 949; H NMR
(400 MHz, DMSO-d6); δ (ppm) 2.43 (m, 2H), 2.77–2.55
(m, 2H), 3.68 (m, 4H), 5.68 (s, 1H), 7.17 (d, J = 8.90 Hz,
FIGURE 2 Energy-dispersive X-ray spectroscopy (EDX) of
nano-[Mg-4MSMP]Cl2

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GOUDARZIAFSHAR ET AL.
FIGURE 3 Energy-dispersive X-ray
spectroscopy (EDX) of nano-[Mg-4MSMP]Cl2
FIGURE 4 SEM micrograph of nano-[Mg-4MSMP]Cl2
FIGURE 5 Thermal gravimetric analysis
(TGA) of nano-[Mg-4MSMP]Cl2 at range of
0–800 ꢀC, with a temperature increase rate of
10 ꢀC

PREPARATION OF 1-(α-AMINOALKYL)-2-NAPHTHOLS
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(d, J = 9.00 Hz, 1H), 6.96–6.88 (m, 1H), 6.78 (m, 1H), 5.72
(s, 1H), 3.94 (s, 3H), 3.61 (s, 4H), 3.52 (s, 3H), 2.59 (s,
2H), 2.38 (m, 2H); 13C NMR (62.5 MHz, DMSO-d6) δ
155.6, 153.8, 151.3, 132.7, 129.7, 129.0, 128.6, 127.9, 127.0,
122.9, 121.4, 119.9, 116.0, 115.5, 113.6, 62.22, 56.7, 55.4.
MP]Cl2) as a nano-Schiff base complex (Scheme 2). The
structure of nano-[Mg-4MSMP]Cl2 was studied by IR,
XRD, EDX, TGA and DTA as well as mass analysis.
At first, (E)-6-(2-hydroxybenzylideneamino)-4-(4-
methoxyphenyl)-3-methyl-1,4-dihydropyrano.
[2,3-c]pyrazole-5-carbonitrile (4MSMP) as a Schiff
base was prepared alone and its structure was studied by
1HNMR and 13CNMR spectra as well as mass analysis.
The related spectra were displayed in supporting
information.
3 | RESULTS AND DISCUSSION
For
the
synthesis
of
nano-Mg-[4-methoxy
phenylsalicylaldiminemethylpyranopyrazole]Cl2 (nano-
[Mg-4MSMP]Cl2), firstly, 4-methoxybenzaldehyde was
reacted with ethyl acetoacetate, malononitrile and hydra-
zine hydrate to afford the related pyranopyrazole
according to previous literature.[29–33] In the next step,
the prepared amine was reacted with salicylaldehyde and
MgCl2.6H2O to give nano-Mg-[4-methoxy phenylsali
In the IR spectrum of the catalyst, a broad peak at
2900–3600 cm−1 was displayed which could be related to
stretching of OH bond in the structure of catalyst.
Another peak, related to stretching mode of C=N bond of
azomethine, which was depicted at 1638 cm−1
(Figure S1).
Energy-dispersive X-ray spectroscopy (EDX) from
the prepared nanoparticles showed the desired
cylaldiminemethylpyranopyrazole]Cl2
(nano-[Mg-4MS
FIGURE 6 Differential thermal
gravimetric (DTG) analysis of nano-[Mg-
4MSMP]Cl2 at range of 0–600 ꢀC, with a
temperature increase rate of 10 ꢀC
TABLE 1 Effect of the catalyst amount, kinds of solvent and temperature on the reaction between 2-naphthol (2 mmol),
4-chlorobenzaldehyde (2 mmol), piperidine (2.2 mmol)
Entry
Solvent
Ethanol
Ethanol
Ethanol
Ethanol
Ethanol
CHCl3
Catalyst amount (mol%)
Temp.(ꢀC)
Time (min)
Yielda (%)
1
2
3
4
5
6
7
8
9
10
10
10
4
25
120
35
35
60
45
35
35
35
35
62
89
89
69
77
95
88
73
-
65
reflux
65
7
65
10
10
10
10
reflux
reflux
65
CH3OH
Ethyl acetate
H2O
65
aIsolated yield.

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GOUDARZIAFSHAR ET AL.
TABLE 2 Synthesis of 1-(α-aminoalkyl)-2-naphthol derivatives catalyzed by nano-[Mg-4MSMP]Cl2
Entry
Product
Time (min)
Yielda (%)
M.p. ꢀC (Lit.)ref
1
35
89
164–165 (164–166)18
2
45
78
125–128 (125–126)19
3
40
85
179–180 (180–182)19
4
44
83
173–175
5
42
71
198–200
6
50
69
174–176 (174–176)20
(Continues)

PREPARATION OF 1-(α-AMINOALKYL)-2-NAPHTHOLS
7 of 10
TABLE 2 (Continued)
Entry
Product
Time (min)
Yielda (%)
M.p. ꢀC (Lit.)ref
199–201 (199–201)21
7
48
73
8
50
69
187–189 (189–190)23
9
38
40
42
85
87
83
161–163 (162–165)19
178–179 (177–179)21
168–170 (169–171)19
10
11
12
45
75
139–141 (140–142)18
13
50
68
145–147
(Continues)

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GOUDARZIAFSHAR ET AL.
TABLE 2 (Continued)
Entry
Product
Time (min)
Yielda (%)
M.p. ꢀC (Lit.)ref
14
35
88
169–171 (170–172)24
15
16
17
38
40
38
90
85
77
129–131 (130–131)19
190–192 (187–190) 22
118–120 (119–121)19
aIsolated yield.
elements including carbon, nitrogen, oxygen, magne-
sium and chlorine in the structure of nano-[Mg-
4MSMP]Cl2 (Figure 2). Therefore, EDX analysis is an
important evidence to confirm the structure of nano-
[Mg-4MSMP]Cl2.
X-ray diffraction analysis (XRD) pattern of nano-[Mg-
4MSMP]Cl2 was also investigated in a domain of 0–90
degree (Figure 4). As it is shown in Figure 3, indicates
that XRD patterns displayed diffraction lines of a high
crystalline nature at about 2θ ≈ 23.0ꢀ, 23.3ꢀ, 26.8ꢀ, 30.1ꢀ,
32.7ꢀ, 38.2ꢀ, 45.3ꢀ and 55.2ꢀ. Crystallite size was studied
by Debye–Scherrer's formula followed by equation:
D = Kλ/ (βcosθ). The crystallite size calculated at about
68.95 nm (for the highest diffraction line at 26.8ꢀ) and
inter planer distance was calculated at about 0.104 nm by
the Bragg equation: dhkl = λ/(2sinθ) (λ: Cu radiation
0.154178 nm).
displayed that the particles of the catalyst were prepared
in nano size (Figure 4).
Thermal gravimetric analysis (TGA) and differential
thermal analysis (DTA) of the nano-[Mg-4MSMP]Cl2 was
also investigated (Figures 5 and 6). As it is shown at
Figures 5 and 6 indicates that nano-[Mg-4MSMP]Cl2
could be used up to 130 ꢀC.
For the optimization of the reaction condition, the
reaction of 2-naphthol (2 mmol), 4-chlorobenzaldehyde
(2 mmol), piperidine (2.2 mmol) in ethanol (10 mL) as
solvent was considered as a model reaction and differ-
ent factors such as catalyst loading, various tempera-
ture and kinds of solvent were studied on the
mentioned reaction. For this purpose, the range of
25 to the reflux temperature of ethanol in the presence
of various amounts of nano-[Mg-4MSMP]Cl2 was tested
which the best result was obtained using 10 mol % of
catalyst at 65 ꢀC. Also, the model reaction was tested
in the absence of catalyst, which the obtained result
The scanning electron microscope (SEM) micro-
graphs of nano-[Mg-4MSMP]Cl2 was also studied and

PREPARATION OF 1-(α-AMINOALKYL)-2-NAPHTHOLS
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2-naphthols, which provided the expected products with
good yields in acceptable reaction times.
ACKNOWLEDGMENTS
The authors gratefully acknowledge the Sayyed
Jamaleddin Asadabadi University for providing support
to this work.
ORCID
Hamid Goudarziafshar https://orcid.org/0000-0002-
5930-6253
Ahmad Reza Moosavi-Zare https://orcid.org/0000-
0003-0321-9326
SCHEME 3 Proposed mechanism for the preparation of 1-(α-
aminoalkyl)-2-naphthols
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We used the optimum conditions for the prepara-
tion of various 1-(α-aminoalkyl)-2-naphthols to deter-
mine the capability of the prepared catalyst. Based on
this, we used a wide range of aromatic aldehydes, con-
taining electron-releasing substituents, electron with-
drawing substituents and halogens, and amines such
as pyrrolidine, piperidine and morpholine in the prepa-
ration of 1-(α-aminoalkyl)-2-naphthols, which provided
the expected products with good yields in acceptable
reaction times (Table 2).
In a suggested mechanism, by the reaction of alde-
hyde, which activated by the catalyst, with an amine,
iminium ion was prepared. In the next step, 2-naphthol
was reacted with prepared iminium ion to give the
expected 1-(α-aminoalkyl)-2-naphthol derivative after
tautomerization (Scheme 3).
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In summary, nano-Mg-[4-methoxy phenylsalicylaldim-
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a novel nanostructured Schiff base complex was synthe-
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SUPPORTING INFORMATION
Additional supporting information may be found online
in the Supporting Information section at the end of this
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How to cite this article: Goudarziafshar H,
Moosavi-Zare AR, Hasani J. Design and
identification of nano-Mg-[4-methoxy phenyl-
salicylaldimine–methyl-pyranopyrzole] Cl2 and its
catalytic application on the preparation of 1-
(α-aminoalkyl)-2-naphthols. Appl Organometal
Chem. 2020;e5372. https://doi.org/10.1002/aoc.
5372