NaHSO4.H2O catalyzed multicomponent synthesis of 1-(Benzothiazolylamino) methyl-2-naphthols under solvent-free conditions

Article abstract of DOI:10.1080/10426507.2012.664221

A one-pot, efficient three-component condensation of aldehydes, 2-naphthol, and 2-aminobenzothiazole in the presence of sodium hydrogen sulfate as an effective catalyst for the synthesis of 1-(benzothiazolylamino)methyl-2-naphthol derivatives under therma

Full text of DOI:10.1080/10426507.2012.664221

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NaHSO4.H2O Catalyzed Multicomponent
Synthesis of 1-(Benzothiazolylamino)
Methyl-2-Naphthols Under Solvent-Free
Conditions
Asghar Hosseinian a & Hamid Reza Shaterian a
a Department of Chemistry, Faculty of Sciences, University of Sistan
and Baluchestan, Zahedan, Iran
Accepted author version posted online: 13 Feb 2012.Version of
record first published: 19 Jun 2012.
To cite this article: Asghar Hosseinian & Hamid Reza Shaterian (2012): NaHSO4.H2O Catalyzed
Multicomponent Synthesis of 1-(Benzothiazolylamino) Methyl-2-Naphthols Under Solvent-Free
Conditions, Phosphorus, Sulfur, and Silicon and the Related Elements, 187:9, 1056-1063
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Phosphorus, Sulfur, and Silicon, 187:1056–1063, 2012
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426507.2012.664221
NaHSO4.H2O CATALYZED MULTICOMPONENT
SYNTHESIS OF 1-(BENZOTHIAZOLYLAMINO)
METHYL-2-NAPHTHOLS UNDER SOLVENT-FREE
CONDITIONS
Asghar Hosseinian and Hamid Reza Shaterian
Department of Chemistry, Faculty of Sciences, University of Sistan
and Baluchestan, Zahedan, Iran
GRAPHICAL ABSTRACT
A
one-pot, efficient three-component condensation of aldehydes, 2-naphthol, and 2-
aminobenzothiazole in the presence of sodium hydrogen sulfate as an effective catalyst for
the synthesis of 1-(benzothiazolylamino)methyl-2-naphthol derivatives under thermal and
solvent-free conditions is described. These products involve two biologically active parts,
Betti’s base and benzothiazole. The present methodology offers several advantages, such as
good yields, short reaction times, and easy work-up.
Keywords 1-(Benzothiazolylamino)methyl-2-naphthols; benzothiazole; Betti’s base; multi-
component reaction
INTRODUCTION
Multicomponent reactions (MCRs) are an attractive synthetic strategy, because com-
plex products are formed in a single step and diversity can be simply achieved by varying
the reaction components.1 Furthermore, multiple molecular scaffolds in both biologically
active and natural compounds can be generated using combinatorial approaches.2 In the
field of medicinal chemistry, functionally substituted starting materials have been used in
multicomponent approaches to obtain desired biologically active compounds.
Preparation of the substituted Betti’s base derivatives become an important area in
synthetic chemistry because of C C bond formation under mild experimental conditions.
In later years, attention has been paid to the Betti’s reaction, and a similar reaction can
Received 18 December 2011; accepted 2 February 2012.
We are thankful to Sistan and Baluchestan University Research Council for partial support of this work.
Address correspondence to Asghar Hosseinian, Department of Chemistry, Faculty of Sciences, Univer-
sity of Sistan and Baluchestan, P.O. Box 98135-674, Zahedan, Iran. E-mail: a.hosseinian.chem@gmail.com;
hrshaterian@hamoon.usb.ac.ir
1056

A. HOSSEINIAN AND H. R. SHATERIAN
1057
Br
F3CO
S
NH2
N
TBN
O
Riluzole
OH
NH OH
O
O
O
NMe2
O
O
HO
O
H
OH
N
N
O
O
O
N
N
S
N
HO
O
OH
R116010
Figure 1 N-tylosil-1-α-amino-(3-bromophenyl)-methyl-2-naphthol (TBN), Riluzole, and R116010.
be performed by either using other naphthols,3 quinolinols,4,5 or by replacing ammonia
with alkyl amines.6–9 The literature reveals that such compounds are gaining the interest
of chemists who are working in the field of asymmetric synthesis.10–12 Also, they can be
used as chiral auxiliaries for the synthesis of α-aminophosphonic acids13 and as chiral shift
reagents for carboxylic acids.14 The racemic aminonaphthols (Betti’s base) have been used
for transformation into products with antibacterial activity. Betti’s base derivatives have
also provided convenient access to many useful synthetic building blocks via the amino
and phenolic hydroxy functional groups.15,16 Recently, it was realized that N-tylosil-1-α-
amino-(3-bromophenyl)-methyl-2-naphthol (TBN (Figure 1)) is a potent modulator of the
P-glycoprotein membrane pump and that the compound could be of clinical relevance to
improve the efficacy of chemotherapy in multidrug resistance cancers.17
Molecules featuring the benzothiazole structural motif play a key part in a wide variety
of chemistry. Their diverse functions range from electron transfer facilitation in the firefly
luciferine cycle18 through antitumor19 and antidiabetic activity20 to Alzheimer disease
tracer21 and anticancer agent in pharmaceutical chemistry.22 The 2-aminobenzothiazole
core, as a privileged scaffold, is found in many natural products and pharmaceuticals that
exhibit remarkable biological activities.23 In addition, some compounds with the skeleton,
which have application in drugs for the treatment of various diseases, are found, such as
tuberculosis,24 epilepsy,25 diabetes,26 glutamate (e.g., Figure 1, Riluzole),27 and tumors
(e.g., Figure 1, R116010).28
Sodium hydrogen sulfate monohydrate (or supported on silica gel) has been
demonstrated to be an efficient catalyst for several reactions such as synthesis of
acyldiazenes,29 Friedel-Crafts reactions of carbonyl compounds with heteroaromatic
compounds in water,30 protection and deprotection,31 nitration,32 nitrosation,33 oxidation,34
synthesis of β-acetamido ketones,35 amidoalkyl naphthols,36 trisubstituted quinolines,37
dibenzo[a,j]xanthene,38 and triarylmethanes.39
Four reports appeared for the synthesis of 1-(benzothiazolylamino)methyl-2-
naphthols using LiCl,40 H6P2W18O62.24H2O (HPA),41 sodium dodecyl sulfate (SDS),42
and 1-methyl-2-pyrrolidonium hydrogen sulfate ([Hnmp]HSO4).43 In continuation of
our interest in the use of ortho-quinone methides (o-QM) as an intermediate in the
synthesis of organic molecules,44 herein, we report a green, one-pot, efficient synthesis
of 1-(benzothiazolylamino)methyl-2-naphthols catalyzed by sodium hydrogen sulfate
NaHSO4.H2O under thermal and solvent-free conditions (Scheme 1).

1058
1-(BENZOTHIAZOLYLAMINO)METHYL-2-NAPHTHOLS
S
N
H
S
N
OH
NaHSO4.H2O (10 mol%)
Solvent-free, Thermal
R
N
CHO
+
NH2
+
R
OH
R= aromatic, aliphatic and heterocyclic ring
Scheme 1 Synthesis of 1-(benzothiazolylamino)methyl-2-naphthols catalyzed by sodium hydrogen sulfate.
RESULTS AND DISCUSSION
In initial studies, we carried out the reaction of 4-chlorobenzaldehyde (1 equiv.),
2-naphthol (1 equiv.), and 2-aminobenzothiazole (1 equiv.) as a model to optimize of reac-
tion conditions. The effects of various catalysts such as ZrO2, Fe2O3, ZnO, MgO, ZnCl2,
MgCl2, CeCl3.7H2O, BiCl3, AlCl3, FeCl3.6H2O, Zn(OAc)2.2H2O, Al(H2PO4)3, 1-butyl-
3-methylimidazolium Chloride ([bmim]Cl), 1,4-diazabicyclo[2.2.2]octane (DABCO), cya-
nuric chloride (C3N3Cl3), N-bromosuccinimide (NBS), and NaHSO4.H2O were studied
(Table 1). Of these, NaHSO4.H2O was found to be the most effective for this conversion
(Table 1, Entry 18).
Next, optimization the amount of NaHSO4.H2O as catalyst and temperature for
the preparation of 1-((benzo[d]thiazol-2-ylamino)(4-chlorophenyl)methyl)naphthalen-2-ol
under solvent-free conditions were investigated (Table 2). The best result was obtained by
◦
carrying out the reaction using 10 mol% of NaHSO4.H2O at 100 C under solvent-free
conditions (Table 2, Entry 3).
Using these optimized reaction conditions, the generality of this reaction was exam-
ined using several types of aldehydes. As shown in Table 3, the direct three-component
reactions worked well with a variety of heterocyclic aldehydes (Table 3, Entries 17, 25,
and 26), aliphatic aldehyde (Table 3, Entry 24), and aryl aldehydes including those bear-
ing electron-withdrawing and electron-donating groups, and the desired compounds were
obtained in good yields. However, the yield of product was lower in comparison with aryl
aldehydes containing electron-withdrawing substituents (Table 3, Entries 14–16).
Table 1 Preparation of 1-((benzo[d]thiazol-2-ylamino)(4-chlorophenyl)methyl)naphthalen-2-ol at 70 ◦C in the
presence of different catalysts (10 mol%) under solvent-free conditionsa
Time (min)/
yield (%)b
Time (min)/
yield (%)b
Entry
Catalysta
Entry
Catalysta
AlCl3
FeCl3.6H2O
Zn(OAc)2.2H2O
Al(H2PO4)3
[bmim]Cl
DABCO
C3N3Cl3
NBS
NaHSO4.H2O
1
2
3
4
5
6
7
8
9
—
ZrO2
Fe2O3
ZnO
MgO
ZnCl2
MgCl2
CeCl3.7H2O
BiCl3
60/Trace
60/65
60/43
25/51
60/20
120/39
19/71
23/73
14/68
10
11
12
13
14
15
16
17
18
20/69
15/48
35/62
53/62
30/65
120/40
18/55
30/65
18/70
aBased on the reaction of 4-chlorobenzaldehyde (1 equiv.), 2-naphthol (1 equiv.), and 2-aminobenzothiazole
(1 equiv.).
bYields refer to isolated pure products.

A. HOSSEINIAN AND H. R. SHATERIAN
1059
Table 2 Optimization the amount of NaHSO4.H2O as catalyst and temperature for the preparation of 1-
((benzo[d]thiazol-2-ylamino)(4-chlorophenyl)methyl)naphthalen-2-ol under solvent-free conditions
Temperature
(◦C)
Time
(min)
Yield
Yield (%)a
Entry
Catalyst (mol%)
1
2
3
4
5
6
7
NaHSO4.H2O (10)
NaHSO4.H2O (10)
NaHSO4.H2O (10)
NaHSO4.H2O (10)
NaHSO4.H2O (15)
NaHSO4.H2O (20)
NaHSO4.H2O (5)
70
85
18
11
6
5
5
70
74
83
82
78
80
77
100
120
100
100
100
5
7
aYields refer to isolated pure products.
As reported in the literature,40–44 the reaction of 2-naphthol with aldehydes in the
presence of an acid catalyst is known to give o-QMs. These o-QMs, generated in situ, react
with 2-aminobenzothiazole to form the desired product (Scheme 2).
To demonstrate the merit of the present work in comparison with previously reported
results, we compared results of LiCl,40 H6P2W18O62.24H2O (HPA),41 and SDS42 in the
Table 3 Preparation of 1-(benzothiazolylamino)methyl-2-naphthol derivatives
Time (min)/
yield (%)a
Entry
Aldehyde
Benzaldehyde
mp (◦C)/Lit. mp[ref]
1
2
10/88
6/84
12/87
6/83
6/79
13/86
7/93
202–204/202–203[43]
187–189/189–190[43]
193–195/192–194[42]
208–210/209–210[40]
206–208/206–207[43]
184–186/176–178[42]
203–205/202–204[42]
168–170/165–167[42]
184–186/184–186[42]
173–175/175–176[40]
160–162/161–163[42]
192–194/194–195[43]
183–185/182–183[40]
212–214/215–216[43]
193–195/191–194[42]
187–189/189–191[42]
210–212/209–211[42]
203–205/–
2-Chlorobenzaldehyde
3-Chlorobenzaldehyde
4-Chlorobenzaldehyde
2,4-Dichlorobenzaldehyde
4-Fluorobenzaldehyde
3-Bromobenzaldehyde
2-Methoxybenzaldehyde
3-Methoxybenzaldehyde
4-Methoxybenzaldehyde
2,4-Dimethoxybenzaldehyde
4-Hydroxy-3-methoxybenzaldehyde
4-Methylbenzaldehyde
2-Nitrobenzaldehyde
3
4
5
6
7
8
9
4/87
9/86
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
10/83
12/84
12/78
10/90
8/63
30/59
30/52
12b/93
8/92
3-Nitrobenzaldehyde
4-Nitrobenzaldehyde
Pyridine-4-carbaldehyde
1-Naphthaldehyde
2,6-Dichlorobenzaldehyde
4-Bromobenzaldehyde
5-Bromo-2-hydroxybenzaldehyde
2,3-Dimethoxybenzaldehyde
2-Methylbenzaldehyde
3-Phenylpropanal
9/84
193–195/–
200–202/–
183–185/–
201–203/–
191–193/–
192–194/–
191–193/–
189–191/–
10/91
10/89
12/81
5/92
5/95
12b/90
9b/88
Thiophene-2-carbaldehyde
Pyridine-3-carbaldehyde
aYields refer to isolated pure products.
bReaction was carried out at 80 ◦C.

1060
1-(BENZOTHIAZOLYLAMINO)METHYL-2-NAPHTHOLS
R
S
S
N
H
H2N
OH
O
R
R
N
O
Catalyst
-H2O
N
+
Catalyst, -H+, +H+
H
OH
o-QMs
Scheme 2 Possible mechanism for one-pot preparation of 1-(benzothiazolylamino)methyl-2-naphthols catalyzed
by sodium hydrogen sulfate.
synthesis of 1-(benzothiazolylamino)methyl-2-naphthol derivatives. As shown in Table 4,
NaHSO4.H2O (0.1 equiv.) can act as an effective catalyst with respect to reaction time and
the obtained products (Table 4).
EXPERIMENTAL
All reagents were purchased from Merck and Aldrich and used without further purifi-
cation. All yields refer to isolated products after purification. Products were characterized
by comparison of spectroscopic data (IR, 1H NMR, 13C NMR spectra) and melting points
with authentic samples. Elemental analyses for C, H, and N were performed using a Heraeus
CHN-O-Rapid analyzer. The NMR spectra were recorded on a Bruker DRX-400 Avanve
instrument. The spectra were measured in DMSO-d6 relative to TMS (0.00 ppm). IR spectra
were recorded on a JASCO FT-IR 460 plus spectrophotometer. All of the compounds were
solid and solid state IR spectra were recorded using the KBr disk technique. Melting points
were determined in open capillaries with a BUCHI 510 melting point apparatus. Thin layer
chromatography (TLC) was performed on silica gel polygram SIL G/UV 254 plates.
General Procedure for the Preparation
of 1-(benzothiazolylamino)methyl-2-naphthols
To a mixture of 2-naphthol (1 mmol), aldehyde (1 mmol), and 2-aminobenzothiazole
(1 mmol), sodium hydrogen sulfate monohydrate (10 mol%) was added. The mixture was
stirred at 100 ◦C (or 80 ◦C for heterocyclic aldehyde) in an oil bath and the reaction was
followed by TLC. After completion, the mixture was cooled to room temperature, and then
water was added to remove NaHSO4.H2O from the reaction mixture. The solid product was
purified by recrystallization or column chromatography. Spectral data for novel products
are given as supplementary material.
Table 4 Comparison of the results of NaHSO4.H2O with other catalysts reported in the literature for syn-
thesis of 1-(benzothiazolylamino)methyl-2-naphthols from aldehydes (1 equiv.), 2-naphthol (1 equiv.), 2-
aminobenzothiazole (1 equiv.)
Entry
Catalyst (amount)
Conditionsa
Time/yield (%)
1
2
3
4
LiCl (0.5 g = 71 equiv.)
HPA (0.5 g)
SDS (0.2 equiv.)
H2O (3 mL), 90 ◦C
Solvent-free, 60 ◦C
H2O (3 mL), 100 ◦C
Solvent-free, 100 ◦C
5–7 h, 88–96
1.3–2 h, 64–92
1–5 h, 71–93
NaHSO4.H2O (0.1 equiv.)
4–30 min, 52–95

A. HOSSEINIAN AND H. R. SHATERIAN
1061
1-((benzo[d]thiazol-2-ylamino)(naphthalen-1-yl)methyl)naphthalen-2-ol (Table
3, Entry 18): Recrystallized from acetic acid: IR (KBr, cm−1): 3314, 3059, 1626, 1597,
1538, 1517, 1447, 1435, 1301, 1268, 1070, 808, 776. 1H NMR (400 MHz, DMSO-d6): δ
(ppm): 7.01 (t, J = 7.6 Hz, 1H), 7.15–7.36 (m, 5H), 7.39–7.52 (m, 3H), 7.62–7.66 (m, 2H),
7.76–7.88 (m, 4H), 7.95 (d, J = 7.6 Hz, 1H), 8.06–8.15 (m, 2H), 9.01 (d, J = 6.4 Hz, 1H,
D2O exchange, NH), 10.24 (s, 1H, D2O exchange, OH). 13C NMR (100 MHz, DMSO-d6):
δ (ppm): 52.6, 118.3, 118.6, 118.9, 119.0, 121.4 (2C), 122.8, 124.0, 125.5, 125.7, 125.9,
126.0, 126.6, 126.7, 128.1, 129.1, 129.2, 129.2, 130.2, 131.2, 131.6, 133.3, 134.1, 137.6,
152.8, 153.8, 165.8. MS m/z (%): 432 (M+, 3), 29 (7), 282 (28), 281 (59), 274 (20), 273
(100), 252 (16), 233 (15), 232 (67), 189 (9), 161 (11), 159 (12), 150 (16), 135 (36), 119
(15), 105 (18), 95 (15), 69 (12), 55 (12), 43 (46). Anal. Calcd for C28H20N2OS: C, 77.75;
H, 4.66; N, 6.48; S, 7.41. Found: C, 77.32; H, 4.96; N, 6.75; S, 7.25.
1-((benzo[d]thiazol-2-ylamino)(5-bromo-2-hydroxyphenyl)methyl)naphthalen-
2-ol (Table 3, Entry 21): Recrystallized from acetic acid: IR (KBr, cm−1): 3355, 3208,
1
3061, 1628, 1575, 1537, 1467, 1435, 1339, 1311, 1267, 1214, 1107, 807, 747. H NMR
(400 MHz, DMSO-d6): δ (ppm): 6.70 (d, J = 8.4 Hz, 1H), 6.99 (t, J = 7.6 Hz, 1H),
7.13–7.39 (m, 6H), 7.46 (t, J = 8.0 Hz, 1H), 7.63–7.68 (m, 2H), 7.74 (d, J = 8.8 Hz,
1H), 7.79 (d, J = 8.0 Hz, 1H), 8.26 (d, J = 8.4 Hz, 1H), 8.72 (s, 1H, D2O exchange,
NH), 9.62–10.28 (broad s, 2H, D2O exchange, 2OH). 13C NMR (100 MHz, DMSO-d6): δ
(ppm): 50.5, 110.3, 117.6, 117.8, 118.4, 118.8, 121.4, 121.7, 123.1, 123.4, 126.2, 126.8,
128.7, 129.0, 129.9, 130.6, 130.8, 130.9, 131.5, 132.9, 152.2, 153.4, 154.4, 166.3. MS m/z
(%): 478 (M+ +1, 2), 476 (M+ –1, 2), 454 (31), 452 (39), 373 (8), 334 (38), 332 (38), 317
(75), 315 (64), 311 (65), 309 (64), 253 (28), 230 (24), 202 (11), 150 (55), 144 (64), 136
(37), 135 (100), 123 (12), 115 (39), 108 (27), 96 (22), 63 (19), 50 (10), 45 (7). Anal. Calcd
for C24H17BrN2O2S: C, 60.38; H, 3.59; N, 5.87; S, 6.72. Found: C, 60.79; H, 3.72; N,
5.54; S, 6.51.
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