Catalytic application of N,2-dibromo-6-chloro-3,4-dihydro-2 H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide on the synthesis of 1-carbamato-alkyl-2-naphthols and 1-thioamido-alkyl-2-naphthols

Article abstract of DOI:10.1080/17415993.2015.1028938

A novel N-bromo sulfonamide reagent, namely N, 2-dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide, is prepared and employed as a new and highly efficient catalyst for the preparation of 1-carbamato-alkyl-2-naphthol and 1-thioamido-alkyl-2-naphthol derivatives.

Full text of DOI:10.1080/17415993.2015.1028938

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Catalytic application of N,2-dibromo-6-
chloro-3,4-dihydro-2H-benzo[e]
[1,2,4]thiadiazine-7-sulfonamide
1,1-dioxide on the synthesis of 1-
carbamato-alkyl-2-naphthols and 1-
thioamido-alkyl-2-naphthols
Ardeshir Khazaeia, Fatemeh Abbasia & Ahmad Reza Moosavi-Zareb
a Faculty of Chemistry, Bu-Ali Sina University, Hamedan
6517838683, Iran
b Department of Chemistry, University of Sayyed Jamaleddin
Asadabadi, Asadabad 6541835583, Iran
Published online: 10 Apr 2015.
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To cite this article: Ardeshir Khazaei, Fatemeh Abbasi & Ahmad Reza Moosavi-Zare (2015):
Catalytic application of N,2-dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-
sulfonamide 1,1-dioxide on the synthesis of 1-carbamato-alkyl-2-naphthols and 1-thioamido-alkyl-2-
naphthols, Journal of Sulfur Chemistry, DOI: 10.1080/17415993.2015.1028938
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Journal of Sulfur Chemistry, 2015
http://dx.doi.org/10.1080/17415993.2015.1028938
Catalytic application of N,2-dibromo-6-chloro-3,4-dihydro-2H-
benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide on the
synthesis of 1-carbamato-alkyl-2-naphthols and
1-thioamido-alkyl-2-naphthols
Ardeshir Khazaeia∗, Fatemeh Abbasia and Ahmad Reza Moosavi-Zareb∗
aFaculty of Chemistry, Bu-Ali Sina University, Hamedan 6517838683, Iran; bDepartment of Chemistry,
University of Sayyed Jamaleddin Asadabadi, Asadabad 6541835583, Iran
(Received 5 January 2015; accepted 9 March 2015)
A novel N-bromo sulfonamide reagent, namely N, 2-dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-
7-sulfonamide 1,1-dioxide, is prepared and employed as a new and highly efficient catalyst for the
preparation of 1-carbamato-alkyl-2-naphthol and 1-thioamido-alkyl-2-naphthol derivatives.
R1
1a-1s, 2a-2i
Keywords: N-halo reagent; benzyl carbamate; thioacetamide; aldehyde; 1-carbamato-alkyl-2-naphthol;
1-thioamido-alkyl-2-naphthol
1. Introduction
Multicomponent reactions (MCRs) are generally defined as reactions where more than two start-
ing materials react to give a product, unifying essentially all of the atoms of the educts.[1,2]
MCRs play a significant role in combinatorial chemistry due to the ability to synthesize target
compounds with greater efficiency and atom economy by forming structural complexity in a
single step from three or more reactants. Also, MCRs offer some advantages of simplicity and
synthetic efficiency over conventional chemical reactions and lead to the preparation of important
heterocyclic rings.[2–4]
1-Amido-alkyl-2-naphthols and 1-thiomido-alkyl-2-naphthols are important compounds
which can be converted to biologically useful 1-aminoalkyl-2-naphthols via hydrolysis of amidic
groups. [5] Based on their wide biological activities, bradycardiac and hypotensive properties
of 1-aminoalkyl-2-naphthols have been examined.[5,6] 1-Amido-alkyl-2-naphthols can be also
*Corresponding authors. Emails: khazaei_1326@yahoo.com, moosavizare@yahoo.com
© 2015 Taylor & Francis

2
A. Khazaei et al.
O
H
O
N
O
N
Br
S
S
Br
O
Cl
N
H
Scheme 1. The structure of DCDBTSD.
Scheme 2. The synthesis of 1-carbamato-alkyl-2-naphthols and 1-thioacetamido-alkyl-2-naphthols.
converted to 1,3-oxazine derivatives.[7] 1,3-Oxazines exhibit several pharmaceutical properties
including antibiotic,[8] antitumor [9] and analgesic activities.[10]
Recently, several synthetic protocols have been reported for the synthesis of 1-amido-alkyl-
2-naphthols and 1-thioamido-alkyl-2-naphtols by multicomponent condensation reactions using
[Dsim]HSO4,[11] TCCA and DCDMH,[12] Trityl chloride,[13] p-TSA,[14] H2SO4/SiO2 [15]
and Fe(HSO4)3.[16] Because of the importance of these compounds, the introduction of a milder,
faster and more eco-friendly method accompanied with higher yields is still needed.
An enormous group of compounds commonly called N-halo reagents are utillized as poten-
tially reactive intermediates. These compounds are widely used in organic transformations. Some
−
specific features of N-halo reagents including the high activity of the N X bond and the var-
ious modes of splitting of this bond cause their wide application in organic synthesis.[17] Due
to significant features of N-halo reagents, a novel and effective N-halo reagent was synthesized
using procedures from prior investigation of this compound class,[18–21] namely N,2-dibromo-
6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide (DCDBTSD)
(Scheme 1).[22] DCDBTSD has been used as an applicable and suitable catalyst for the synthesis
of 1-amido-alkyl (carbamato/thioacetamido)-2-naphthol via one-pot three-component condensa-
tion reaction of arylaldehydes, 2-naphthol and benzyl carbamate/thioacetamide at 80°C under
solvent-free conditions (Scheme 2).
2. Results and discussion
1
The structure of DCDBTSD was identified by IR, H and 13C NMR, X-ray diffraction as well
as mass spectra. The IR spectrum of the catalyst and hydrochlorothiazide is displayed in Figure
S1. Comparison of IR spectra of hydrochloroyhiazide and DCDBTSD demonstrated that two
sharp peaks for the N-H groups of the hydrochlorothiazide at 3363 and 3169 cm–1 were elim-
inated in DCDBTSD. These differences provide evidence that the two hydrogens of the N-H
groups in hydrochlorothizide were replaced with two N-Br groups in DCDBTSD (Figure S1)
(see supplementary data, http://dx.doi.org/ doi:10.1080/17415993.2015.1028938).
In another study, thermal gravimetric (TG) and derivative thermal gravimetric (DTG) analysis
of DCDBTSD were investigated in the range of 30–618°C, with a temperature rate increase of

Journal of Sulfur Chemistry
3
10°C min−1 in a nitrogen atmosphere. The corresponding diagrams are shown in Figure S2. In
the TG pattern of DCDBTSD multistage decomposition is observed. Therefore, DCDBTSD can
be used as a catalyst below 200°C, but decomposes above 255°C (Figure S2) (see supplementary
data, http://dx.doi.org/ doi:10.1080/17415993.2015.1028938).
After full characterization of DCDBTSD, its catalytic activity for the preparation of 1-
carbamato-alkyl-2-naphthol and 1-thioacetamido-alkyl-2-naphthol was examined.
Initially, to optimize the reaction conditions (amount of catalyst and temperature), as a
model reaction, the condensation of 2-naphthol (1 mmol), benzaldehyde (1 mmol) and benzyl
carbamate (1.1 mmol) was studied in the presence of different amounts of DCDBTSD, over a
range of 70–90°C under solvent-free conditions. The results are summarized in Table 1.
Table 1. Optimization of the reaction conditions for the synthesis of 1-carbamato-alkyl-2-naphthol.
Entry
Catalyst (mol%)
Temperature (°C)
Time(min)
Yielda (%)
1
2
3
4
5
6
7
No catalyst
Hydrochlorothiazide
80
80
80
80
80
70
90
180
180
4
2
2
–
–
5
77
86
86
80
85
10
15
10
10
5
2
aIsolated yield.
Table 2. Preparation of 1-carbamato-alkyl-2-naphthols and 1-thioacetamido-alkyl-2-naphthols using DCDBTSD at
80°C.
Mp. °C
Entry
R1/R2
X
Time (min)/yielda (%)
Found
Ref.
1a
1b
1c
1d
1e
1f
1g
1h
1i
C6H5/ PhCH2O
2-NO2C6H4/PhCH2O
3-NO2C6H4/PhCH2O
4-NO2C6H4/PhCH2O
2-ClC6H4/PhCH2O
3-ClC6H4/PhCH2O
4-ClC6H4/PhCH2O
2,3-diClC6H3/PhCH2O
2,4-diClC6H3/PhCH2O
2-FC6H4/PhCH2O
3-FC6H4/PhCH2O
4-FC6H4/PhCH2O
2-BrC6H4/PhCH2O
3-BrC6H4/PhCH2O
4-BrC6H4/PhCH2O
1-C10H7/PhCH2O
2-C10H7/PhCH2O
4-CH3C6H4/PhCH2O
2-OCH3C6H4/PhCH2O
C6H5/Me
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
O
S
10/86
4/85
3/84
2/88
2/83
3/85
4/86
2/93
2/92
4/87
6/80
3/80
2/83
3/90
3/77
6/79
4/80
11/65
10/79
25/80
30/78
20/83
20/84
20/88
30/83
40/77
35/75
45/60
185–187
200–202
201–202
203–205
210–211
185–187
180–181
218–220
208–210
188–189
208–210
209–210
220–221
183–185
180–181
214–216
210–211
154–155
202–203
185–187
190–191
256–258
243–245
219–221
203–205
195–196
185–187
181–182
[12]
[12]
[12]
[12]
[12]
[12]
[12]
–
[23]
–
–
[12]
–
–
[12]
[12]
–
[12]
[12]
[13]
–
–
[16]
–
1j
1k
1l
1m
1n
1o
1p
1q
1r
1s
2a
2b
2c
2d
2e
2f
3-NO2C6H4/Me
3-ClC6H4/Me
4-ClC6H4/Me
2,4-diClC6H3/Me
4-FC6H4/Me
4-BrC6H4/Me
4-CH3C6H4/Me
4-OCH3C6H4/Me
S
S
S
S
S
S
S
S
–
–
–
[16]
2g
2h
2i
aYield of the purified product.

4
A. Khazaei et al.
As it is shown in Table 1, higher yield and shorter reaction time are achieved using 10 mol%
of catalysts at 80°C under solvent-free conditions. No improvement in the reaction results was
observed by increasing the quantities of the catalyst and the temperature. The solvent-free con-
densation was also examined at 80°C without catalyst and with hydrochlorothiazide and no
reaction was observed even after long reaction time (3 h).
To evaluate the efficiency of the organic catalyst in the synthesis of 1-carbamato-alkyl-
2-naphthols and 1-thioacetamido-alkyl-2-naphthols, the reaction of 2-naphthol and benzyl
carbamate or thioacetamide with structurally different aromatic aldehydes in the presence of
DCDBTSD as a catalyst was investigated under optimized conditions. The obtained results are
described in Table 2. As it can be observed in Table 2, several aromatic aldehydes including
electron-releasing- and electron-withdrawing substituents and halogens on the aromatic ring of
aldehydes were successfully reacted and produced corresponding products in good to high yields
and in relatively short reaction times.
Based on published reports [12,24,25] and the suggested mechanism (Scheme 3), the reaction
is catalyzed by in situ generated Br+ from the DCDBTSD. Therefore, in the catalytic process the
aldehyde abstracts Br+ from DCDBTSD to generate intermediates I and II as activated forms
of the aldehyde. These complexes function as activated carbonyl compounds and react with 2-
naphthol to give intermediate III, which is converted to IV after tautomerization. Finally, by the
reaction of benzyl carbamate or thioacetamide with IV and the elimination of one molecule H2O,
the desired product is obtained and the catalyst is generated.
To demonstrate the formation of intermediates I and II, benzaldehyde was reacted with cata-
lyst at 80°C, and then IR and UV spectra of the carbonyl functional group in the reaction mixture
was compared with benzaldehyde. The observed decrease in the IR (nujol): ν (cm−1) of C O
=
benzaldehyde from 1704 to 1692 in the reaction mixture is indicative of the decreased nature
of the double bond and formation of an activated carbonyl (Figure S4). Also, the IR spectrum
of this complex is revealed by two peaks sharp at 3380 and 3253 cm−1. From these results, the
Scheme 3. The plausible mechanism for the synthesis of 1-amido-alkyl (carbamato-alkyl or thioamido-alkyl)-
2-naphthols catalyzed by DCDBTSD.

Journal of Sulfur Chemistry
5
proposed mechanism is confirmed and the catalyst is completely recovered during the reaction
(Figure S3) (see supplementary data, http://dx.doi.org/ doi:10.1080/17415993.2015.1028938).
In another evidence, to demonstrate the formation of intermediates I and II, UV spectra of
benzaldehyde, catalyst and the mixture of benzaldehyde and catalyst were studied. The maximum
absorption of benzaldehyde and catalyst appeared at 289 and 333 nm, respectively. But λmax of
the complex of benzaldehyde with Br+, which was formed by the reaction of DCDBTSD with
benzaldehyde, was observed at 282 nm (Figure S4) (see supplementary data, http://dx.doi.org/
doi:10.1080/17415993.2015.1028938).
3. Conclusions
In conclusion, this paper offers a clean, efficient and simple procedure for preparation of
1-carbamato-alkyl-2-naphthol and 1-thioacetamido-alkyl-2-naphthol derivatives via one-pot,
three-component condensation of arylaldehyde and 2-naphthol with amide (benzyl carbamate
or thioacetamide) using DCDBTSD as new, effective and homogenous organic catalysts at 80°C
under the solvent-free and neutral conditions.
4. Experimental
4.1. General
Chemicals were purchased from Merck and Aldrich Chemical Companies and used without
further purification. All yields refer to isolated products after purification. The reactions were
monitored by thin-layer chromatography (TLC) carried out on silica plates. The products were
characterized by comparison of their physical data with those of known samples or by their spec-
tral data. Infrared (IR) spectra were recorded on a Shimadzu IR 470 spectrophotometer. The 1H
NMR (400 or 90 MHz) and 13C NMR (100 Hz or 22.5 MHz) were run on a Bruker AVANCE-
DRX. Mass spectra were recorded on an Agilent technologies (HP) 5973 network mass-selective
detector (MSD) operating at an ionization potential of 70 eV. Melting points were determined in
open capillaries with a Stuart Scientific melting point apparatus. TLC was performed on Silica-
gel polygram SILG/UV 254 plates. TG and DTG were analyzed by a Perkin Elmer (Model: Pyris
1) (30–618°C, temperature increase rate of 10°C min−1, nitrogen atmosphere).
4.2. General procedure for the synthesis of DCDBTSD
A solution of sodium hydroxide (6 mol Lit−1, 1 mL) was added dropwise to a stirring round-
bottomed flask (50 mL) containing hydrochlorothizide (0.6 g, 2 mmol) in distillated water
(2 mL) over a period of 10 min at room temperature. After the addition was completed, the reac-
tion mixture was stirred for 20 min. Then, to the stirring solution of hydrochlorothiazide, bromine
(0.16 mL, 3 mmol) was slowly added over a period of 15 min at 0°C. The insoluble brominated
catalyst was removed by filtration and washed with H2O (10 mL) to give DCDBTSD in 90%
yield (0.82 g).[22]
4.2.1. N,2-dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide
1,1-dioxide
Yield 90%; White solid; 255 ◦C;1H NMR (400 MHz, DMSO-d6): δ (ppm) 4.70 (s, 2H), 6.85 (s,
1H), 7.20 (s, 1H), 7.88 (s, 1H), 8.07 (s, 1H); 13C NMR (100 MHz, DMSO-d6): δ (ppm) 55.08,

6
A. Khazaei et al.
107.26, 110.65, 122.57, 127.55, 136.34, 142.14; IR (KBr) ν/cm−13377, 3232, 1579, 1495, 1362,
1308, 1244, 1147, 1058, 1025, 794, 716, 675, 579, 545;MS m/z observed: 455 (M+).
4.3. General procedure for the synthesis of 1-carbamato-alkyl-2-naphtols using DCDBTSD
(compound 1a–1s)
A mixture of 2-naphthols (0.288g, 2 mmol), aldehydes (2 mmol), benzylcarbamate (0.320 g, 2.2
mmol) and DCDBTSD (0.091 g, 10 mol%) in a 10 mL round-bottomed flask connected to a
reflux condenser, was stirred in oil bath (80°C) for the appropriate time (Table 2). After comple-
tion of the reaction, as monitored by TLC, the reaction mixture was cooled to room temperature
and recrystallized from ethanol (95%).
4.3.1. Benzyl (2,3-dichlorophenyl)(2-hydroxynaphthalen-1-yl)methylcarbamate (1h)
1
Yield 93%; white solid; mp 218–220◦C; H NMR (400 MHz, DMSO-d6): δ (ppm) 5.02 (2H),
6.84 (d, J = 8 Hz, 1H); 7.09 (d, J = 7.2 Hz, 2H), 7.26–7.31 (6H), 7.39 (d, J = 8 Hz, 1H), 7.47
(d, J = 8 Hz, 1H), 7.51 (d, J = 8 Hz, 1H), 7.72 (d, J = 8 Hz, 1H), 7.76 (d, J = 8 Hz, 1H), 7.96
(d, J = 8 Hz, 1H), 8.17 (d, J = 8 Hz, 1H), 9.92 (s, OH, 1H); 13C NMR (100 MHz, DMSO-d6):
δ (ppm) 52.04, 67.04, 117.74, 120.07, 124.03, 124.26, 128.12, 129.04, 129.33, 129.90, 130.28,
131.38, 134.20, 138.67, 143.91, 155.17, 157.71; IR (KBr) ν/cm−13414, 3295,1702, 1685, 1629,
1515, 1451, 1338, 1271, 1050, 781, 744, 720, 558; MS m/z observed:451 (M+).
4.3.2. Benzyl (2-fluorophenyl)(2-hydroxynaphthalen-1-yl)methylcarbamate (1j)
Yield 87%; white solid; mp 188–189◦C; 1H NMR (400 MHz, DMSO-d6): δ (ppm) 5.02 (s, 2H),
7.01–7.15 (b, 5H), 7.26–7.38 (b, 6H), 7.49 (2H), 7.71–7.77 (2H), 7.92 (s, 1H), 8.04 (s, 1H),
10.18 (s, 1H, OH); 13C NMR (100 MHz, CDCl3): δ (ppm) 47.62, 67.23, 116.62, 116.83, 118.86,
119.98, 124.12, 125.41, 128.07, 129.24, 129.44, 129.94, 130.19, 130.34, 130.66, 131.16, 133.55,
138.49, 154.72, 157.24, 161.44; IR (KBr) ν/cm−1 3427, 3279, 1689, 1630, 1525, 1435, 1342,
1271, 1043, 935, 86, 771, 747; MS m/z observed:401 (M+).
4.3.3. Benzyl (3-fluorophenyl)(2-hydroxynaphthalen-1-yl)methylcarbamate (1k)
Yield 80%, white solid; mp 208–210◦C; 1H NMR (400 MHz, DMSO-d6): δ (ppm) 5.06 (s, 2H),
6.88 (s, 1H), 7.06 (d, J = 8.4 Hz, 2H), 7.25–7.33 (b, 10H), 7.78 (d, J = 8.4 Hz, 2H), 7.90 (s,
2H), 10.23 (s, 1H, OH); 13C NMR (100 MHz, DMSO-d6): δ (ppm) 51.64, 67.42, 116.33, 116.54,
120.04, 120.15, 124.24, 128.30, 129.39, 129.45, 129.52, 129.60, 130.26, 131.14, 133.56, 138.46,
140.00, 154.53, 157.70, 161.32; IR (KBr) ν/cm−1 3425, 3250, 1677, 1506, 1439, 1327, 1218,
1065, 943, 704; MS m/z observed:401 (M+).
4.3.4. Benzyl (2-bromophenyl)(2-hydroxynaphthalen-1-yl)methylcarbamate (1m)
Yield 83%, white solid; m p 220–221 ◦C; 1H NMR (400 MHz, DMSO-d6): δ (ppm) 5.00 (s, 2H),
6.79 (s, 1H), 7.12 (s, 1H), 7.28–7.43 (b, 10H), 7.52 (1H), 7.75 (2H), 8.00 (2H), 9.95 (s, 1H, OH);
13C NMR (100 MHz, CDCl3): δ (ppm) 53.65, 66.89, 118.42, 120.09, 123.97, 124.46, 127.93,
128.68, 128.91, 129.24, 129.84, 130.20, 130.48, 131.15, 131.71, 134.27, 155.07, 157.11; IR
(KBr) ν/cm−1 3422, 3170, 1701, 1627, 1516, 1435, 1334, 1275, 1247, 1046, 753, 731, 527;
MS m/z observed:461 (M+).

Journal of Sulfur Chemistry
7
4.3.5. Benzyl (2-hydroxynaphthalen-1-yl)(naphthalen-2-yl)methylcarbamate (1q)
Yield 80%; white solid; mp 210–211◦C1H NMR (400 MHz, DMSO-d6): δ (ppm) 5.05 (d,
J = 12.4 Hz, 1H), 5.12 (d, J = 12.8 Hz, 1H), 7.06 (d, J = 5.6 Hz, 1H), 7.23 (d, J = 8, 2H),
7.32–7.43 (m, 10H), 7.78 (b, 5H), 7.97 (b, 2H), 10.18 (s, OH, 1H); 13C NMR (100 MHz, CDCl3):
δ (ppm) 52.16, 67.38, 120.05, 120.21, 124.19, 124.71, 125.48, 128.99, 129.26, 129.40, 129.98,
130.23, 131.15, 133.43, 133.73, 134.30, 138.57, 141.56, 154.65, 157.76; IR (KBr) ν/cm−1
3413, 3169, 1676, 1583, 1519, 1437, 1332, 1272, 1051, 938, 814, 732, 601, 473; MS m/z
observed:433 (M+).
4.4. General procedure for the synthesis of 1-thioamido-alkyl-2-naphtols using DCDBTSD
(compound 2a–2i)
A mixture of 2-naphthols (0.288g, 2 mmol), aldehydes (2 mmol), thioacetamide (0.180 g, 2.4
mmol) and DCDBTSD (0.091 g, 10 mol%) in a 10 mL round-bottomed flask connected to
a reflux condenser, was stirred in oil bath (80°C) for the appropriate time (Table 2). After
completion of the reaction, as monitored by TLC, the crude products were purified by plate
chromatography on silica gel eluted with EtOAc/n-hexane.
4.4.1. N-((3-Chlorophenyl)(2-hydroxynaphthalen-1-yl)methyl) thioacetamide (2c)
Yield 83%; white solid; mp 255–258°C; 1H NMR (400 MHz, DMSO-d6): δ (ppm) 1.97 (s, 3H,
CH3), 7.04–7.10 (m, 2H), 7.17–7.29 (m, 6H), 7.37–7.41 (m, 1H), 7.76–7.82 (m, 2H), 8.51 (d,
J = 8 Hz, 1H), 10.08 (s, 1H, OH); 13C NMR (DMSO-d6): δ (ppm) 23.04, 47.95, 118.78, 118.91,
122.97, 123.37, 125.28, 126.13, 126.54, 127.03, 128.81, 129.09, 130.03, 130.39, 132.68, 133.25,
145.92, 153.73, 169.93; IR (KBr) ν/cm−1 3410, 3168, 1647, 1597, 1574, 1516, 1439, 1335, 1281,
1192, 1066, 812, 744, 716; MS m/z observed: 341 (M+).
4.4.2. N-((2,4-Dichlorophenyl)(2-hydroxynaphthalen-1-yl)methyl)thioacetamide (2e)
1
Yield 84%; white solid; mp 218–220°C; H NMR (400 MHz, DMSO-d6): δ (ppm) 1.92 (s,
3H, CH3), 6.98 (s, J = 8 Hz, 1H), 7.10 (d, J = 8.8 Hz, 1H), 7.27 (d, J = 7.7 Hz, 1H), 7.36–
7.46 (m, 3H), 7.59(d, J = 8 Hz, 1H), 7.73 (d, J = 8.8 Hz, 1H), 7.79 (d, J = 7.6 Hz, 1H),
7.95 (d, J = 8.4 Hz, 1H), 8.64 (s, 1H), 9.89(s, 1H, OH); 13C NMR (DMSO-d6): δ (ppm)
22.82, 47.78, 116.80, 119.11, 122.80, 122.99, 126.85, 126.95, 128.67, 128.90, 129.11, 130.10,
131.70, 132.09, 133.22, 133.31, 139.81, 154.28, 169.31; IR (KBr) ν/cm−1 3405, 3118, 1650,
1581, 1517, 1438, 1369, 1321, 1279, 1163, 1088, 1063, 870, 814, 750; MS m/z observed:
376 (M+).
4.4.3. N-((4-Fluorophenyl)(2-hydroxynaphthalen-1-yl)methyl)thioacetamide (2f)
Yield 83%; white solid; m p 202–203°C; 1H NMR (400 MHz, DMSO-d6): δ (ppm) 1.95 (s, 3H,
CH3), 7.04–7.07 (b, 3H), 7.16–7.23 (m, 4H), 7.33–7.38 (b, 1H), 7.72–7.79 (m, 3H), 8.51 (m,
1H), 10.21 (s, 1H, OH); 13C NMR (100 MHz, DMSO-d6): δ (ppm) 24.26, 56.51, 116.14, 116.35,
120.08, 120.26, 123.91, 124.62, 127.98, 129.49, 129.57, 129.94, 130.17, 130.90, 133.85, 140.39,
155.12, 161.11, 170.84; IR (KBr) ν/cm−1 3396, 3077, 3055, 2975, 1627, 1581, 1510, 1439, 1335,
1276, 1160, 1064, 984, 820, 748; MS m/z observed: 325 (M+).

8
A. Khazaei et al.
Acknowledgements
The authors acknowledge to Bu-Ali Sina University Research Councils, Center of Excellence in Development of
Chemistry Methods (CEDCM) and National Foundation of elites (BMN) for support of this work.
Disclosure statement
No potential conflict of interest was reported by the authors.
Funding
This work was supported by Bu-Ali Sina University, Hamedan 6517838683, Iran and University of Sayyed Jamaleddin
Asadabadi, Asadabad 6541835583, Iran.
Supplemental data
This article makes reference to supplementary material available on the publisher’s website at http://dx.doi.org/
doi:10.1080/17415993.2015.1028938.
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