In this work, four new benzo[d]thiazole derivatives were synthesized successfully from vanillin. Nitration of vanillin gave nitrovanillin followed by cyclization reaction with o-aminothiophenol under microwave irradiation in 4 minutes to give nitroaromatic compound 3. The reduction to convert the nitro group to amino group was optimized. It was found that Fe/ con. HCl in ethanol was the best condition for this case about both yield (~95 %) and simple procedure to give compound 4 as a salt. Acetylation occurs at both phenolic hydroxyl group and amino group of the salt 4 to form N,O-acetyl compound 5. Under mild hydrolysis 5 produces N-acetyl compound 6. The structures of these compounds were established by IR, 1H and 13C NMR and mass spectral analyses. Keywords. benzo[d]thiazole, vanillin, reduction, microwave

Anh Tuyet, Vu Thi

Duong, Le Thanh

Hien, Nguyen

Hoan, Duong Quoc

Vietnam Academy of Science and Technology: Journals Online

  
Vietnam Journal of Chemistry, International Edition, 55(4): 433-437, 2017 
DOI: 10.15625/2525-2321.2017-00486 
433 
 
 
 
Preparation of some new benzo[d]thiazole derivatives 
Duong Quoc Hoan
1*
, Vu Thi Anh Tuyet
2
, Le Thanh Duong
1
, Nguyen Hien
1 
1
Department of chemistry, Hanoi National University of Education 
2
Department of science, Lang Son College of Education 
Received 9 February 2017; Accepted for publication 28 August 2017 
 
Abstract 
In this work, four new benzo[d]thiazole derivatives were synthesized successfully from vanillin. Nitration of 
vanillin gave nitrovanillin followed by cyclization reaction with o-aminothiophenol under microwave irradiation in 4 
minutes to give nitroaromatic compound 3. The reduction to convert the nitro group to amino group was optimized. It 
was found that Fe/ con. HCl in ethanol was the best condition for this case about both yield (95 %) and simple 
procedure to give compound 4 as a salt. Acetylation occurs at both phenolic hydroxyl group and amino group of the salt 
4 to form N,O-acetyl compound 5. Under mild hydrolysis 5 produces N-acetyl compound 6. The structures of these 
compounds were established by IR, 
1
H and 
13
C NMR and mass spectral analyses.  
Keywords. Benzo[d]thiazole, vanillin, reduction, microwave. 
 
1. INTRODUCTION 
 
Benzo[d]thiazole was first synthesized in 1880 by 
Hofmann A. W from formic acid and o-
aminothiphenol [1]: however, the application of 
benzo[d]thiazole derivatives has been studied 
recently and in the past two decades they have been 
extensively studied for their anticancer activity 
[2,3,4]. For example, 2-(4-aminophenyl) 
benzothiazoles (A), an amino aromatic compound, 
and their corresponding N-acetylated derivatives (B) 
have shown surprisingly remarkable anticancer 
activity against certain cancer cell lines particularly 
against breast, colon and ovarian cell lines in vitro 
anticancer screening [5, 6]. Surprisingly, compound 
C exhibited remarkably potent anticancer activity 
[7]. In 2013, J. Pan et al. showed that complexes D 
of Re metal containing benzo[d]thiazole with 
various substituent Rs exhibited the lipophilicities in 
range logPC18 = 1-4, their binding affinities (Ki = 30-
617 nM) to A1-40 fibrils. Nitroaromatic compounds 
play an essential role not only in organic synthesis 
but also in human life. For instance, they are 
pesticides, bacterial degradation, etc. [8]. Therefore, 
in this work, benzo[d]thiazole derivatives E were 
designed by retaining the structure of vanillin and 
connecting with a benzo[d]thiazole ring synthesized 
from vanillin, figure 1. To take advantages of amino, 
amide and nitroaromatic compounds, R1 is either 
NO2 group, an amino group or an acetamido groups. 
R2 is an acetyl group or a hydrogen atom as vanillin 
moiety. 
 
NH2
S
N
OMe
NHCOCH3
S
N
OMe
OMe
S
N
OMe
N
S
A B
C D
S
N
OMe
OR2
R1
Benzo[d]thiazole- Aromatic ring 
making the core structure
EF R
Re complex
 
 
Figure 1: Examples of benzo[d]thiazole derivatives and Design target compounds E 
  
VJC, 55(4), 2017  Duong Quoc Hoan et al. 
434 
2. EXPERIMENTAL  
 
2.1. General  
 
Solvents and other chemicals were purchased from 
Sigma-Aldrich, Merck and used as received, unless 
otherwise indicated. The 
1
H NMR and 
13
C NMR 
spectra were recorded on the Bruker Avance 500 
NMR spectrometer in deuterated solvents such as 
CDCl3, DMSO, and or D2O. Chemical-shift data for 
each signal was reported in ppm unit. IR spectra 
were recorded on the Mattson 4020 GALAXY 
Series FT-IR. Mass spectra were obtained from 
Mass Spectrometry Facility of The Vietnam 
Academy of Science and Technology on LC-MSD-
Trap-SL spectrometer. 
 
2.2. Synthetic procedure 
 
2.2.1. Synthesis of 4-hydroxy-3-methoxy-5-
nitrobenzaldehyde (2) [9, 10] 
  
Concentrated HNO3 (2 mL) was carefully added to a 
cooled (5 °C) solution of vanillin (5 g, 33 mmol) and 
acetic acid (50 mL) over a period of 30 min. The 
gold colored precipitate that formed was filtered, 
washed with water, and allowed to dry (5.21 g, 80 
%): mp. 171 °C. 
 
2.2.2. Synthesis of 4-(benzo[d]thiazol-2-yl)-2-
methoxy-6-nitrophenol (3) 
 
4-Hydroxy-3-methoxy-5-nitrobenzaldehyde (2, 0.55 
g, 3.3 mmol) and 2-aminothiophenol (0.35 mL, 3.3 
mmol) were mixed well in an 100 mL beaker. The 
resulting mixture was irradiated with a domestic 
microwave oven for 4 minutes at 400 W level. The 
mixture was stood for cooling down at room 
temperature and solidifying. The by re-
crystallization from hot ethyl acetate/n-hexane (1:1) 
yielded the title compound 3 as a pale pink solid 
(0.98 g, 98 %, 302.3 g/mol), mp. 163 °C. IR (cm
-1
): 
3435 (br), 3100, 2914, 2852, 1613, 1545, 1430, 
1263, 1143, 1021. 
1
H NMR (DMSO-d6, 500 MHz)  
(ppm): 8.14 (d, J = 8.0 Hz, 1H), 8.08 (s, 1H), 8.06 
(d, J = 8.0, 1H), 7.83 (s, 1H), 7.55 (t, J = 7.5, 1H), 
7.46 (t, J = 7.5, 1H), 4.02 (s, 3H); 
13
C NMR 
(DMSO-d6, 125 MHz)  (ppm): 165.44, 153.34, 
150.12, 145.08, 137.30, 134.50, 126.78, 125.60, 
123.26, 122.76, 122.35, 115.38, 113.01, 56.87; ESI-
MS m/z: 273 [C14H11NO3S]
+
 and 271 [C14H9NO3S]
-
. 
 
2.2.3. Synthesis of 2-amino-4-(benzo[d]thiazol-2-yl)-
6-methoxyphenol hydrochloride (4) 
Iron powder (8 g, 0.14 mol) was added portionwise 
with stirring to a hot mixture of 4-(benzo[d]thiazol-
2-yl)-2-methoxy-6-nitrophenol (3) (6.4 g, 20 mmole) 
in ethanol (20 ml) and concentrated hydrochloric 
acid (30 ml) at reflux temperature. After completion 
of the addition, the refluxing was continued for 6 
hours. Upon cooling a yellow precipitate formed, 
which was filtered off, washed with ethanol, dried to 
yield the title product as a yellow powder (5.6 g, 
95%, 308.8 g/mol) mp: decomposed at 280 °C. IR 
(cm
-1
): 3100, 2954, 2797, 3100-2500 (br), 1540, 
1401, 1170. 
1
H NMR (D2O, 500 MHz)  (ppm): 
7.31 (d, J = 8.0 Hz, 1H),  7.15 (s, 1H), 7.94 (d, J = 
5.0 Hz, 1H), 6.80 (d, J = 6.5 Hz, 1H), 6.75 ( s, 1H), 
6.40 (s, 1H), 3.46 (s, 3H); 
13
C NMR (D2O, 125 
MHz)  (ppm): 167.31, 149.09, 147.60, 142.87, 
137.30, 132.08, 126.78, 125.58, 121.45, 119.88, 
117.45, 114.05, 108.90, 55.86. ESI-MS m/z: 273 
[C14H13N2O2S]
+
 and 271 [C14H11N2O2S]
-
. 
 
2.2.4. Synthesis of 2-acetamido-4-(benzo[d]thiazol-
2-yl)-6-methoxyphenyl acetate (5) 
 
To a solution of 2-amino-4-(benzo[d]thiazol-2-yl)-6-
methoxyphenol hydrochloride (4) (0.3 g, 1 mmol) 
and triethyl amine (0.42 mL, 3 mmol) was added 
acetic anhydride (0.3 mL, 2.5 mmol) in DMF (5 
mL). The resulting solution was stirred at room 
temperature for 1 h. The solvent was evaporated in 
vacuum. Water was added to obtain solid. Re-
crystallization in ethanol 96 % gave 2-acetamido-4-
(benzo[d]thiazol-2-yl)-6-methoxyphenyl acetate (5) 
as a white crystal in 80 % (285 mg, 356.4 g/mol). IR 
(cm
-1
): 3347, 3169, 2923, 2837, 1735, 1692, 1605, 
1543, 1217, 1103. 
1
H NMR (DMSO-d6, 500 MHz)  
(ppm): 9.58 (s, 1 H), 8.43 (s, 1H), 8.15 (d, J = 8.0 
Hz, 1H), 8.09 (d, J = 8.0 Hz, 1H), 7.56 (t, J = 8.0 
Hz, 1H), 7.52 (s, 1H), 7.47 (t, J = 7.5 Hz, 1H), 3.90 
(s, 3H), 2.33 (s, 3H), 2.14 (s, 2H). 
13
C-NMR 
(DMSO-d6, 125 MHz)  (ppm): 169.11, 167.89, 
166.72, 153.45, 151.71, 134.56, 132.69, 131.5, 
130.42, 126.70, 125.58, 122.88, 122.36, 113.89, 
105.51, 56.29, 23.85, 20.79. ESI-MS m/z: 357 
[C18H17N2O4S]
+
 and 355 [C18H15N2O4S]
-
. 
 
2.2.5. Synthesis of N-(5-(benzo[d]thiazol-2-yl)-2-
hydroxy-3-methoxyphenyl)acetamide (6) 
 
To a solution of 2-acetamido-4-(benzo[d]thiazol-2-
yl)-6-methoxyphenyl acetate (5) (0.356 g, 1 mmol) 
in MeOH/H2O (1:2), (5 mL) was added LiOH (60 
mg, 2.5 mmol). The mixture was refluxed until all 
solid was dissolved completely, then acidified with 
(1:1) HCl up to pH = 5. The precipitate was 
  
VJC, 55(4), 2017  Preparation of some new… 
435 
collected as a white crystal (0.3 g, 95 %), mp: 172 
°C. IR (cm
-1
): 3325 (br), 3080, 2928, 2817, 2797, 
1690, 1542, 1401, 1179; 
1
H-NMR (CDCl3, 500 
MHz)  (ppm): 8.33 (s, 1H), 8.00 (d, J = 8.5 Hz, 
1H), 7.86 (d, J = 7.5 Hz, 1H), 7.79 (br, 1H), 7.53 (d, 
J = 1.5 Hz, 1H), 7.45 (t, J = 8.0 Hz, 1H), 7.34 (t, J = 
8.0 Hz, 1H), 7.18 (s, 1H), 3.96 (s, 3H), 2.26 (s, 3H); 
13
C-NMR (CDCl3, 125 MHz)  (ppm):169.18, 
168.14, 154.02, 147.62, 138.06, 135.08, 132.50, 
126.21, 125.72, 124.91, 122.78, 121.59, 113.80, 
105.60, 56.44, 24.50; ESI-MS m/z: 315 
[C16H15N2O3S]
+
, 313 [C16H13N2O3S]
-
. 
 
3. RESULTS AND DISCUSSION 
 
3.1. Synthesis  
 
The series of benzo[d]thiazole derivatives was 
driven as shown in the Scheme 1. First,  nitration of 
vanillin was carried out in 80 % yield to give 
nitrobenzaldehyde 2. Then, the benzo[d]thiazole 
cyclization was furnished in 4 minutes when the 
nitrobenzaldehyde 2 was treated with o-
aminothiophenol to yield nitroaromatic compound 3 
in 98 % yield. 
 
    
OH
S
N
3, 95-98%
NH2•HCl
OH
OCH3
S
N
4, 90-100%
Fe/HCl
CHOH3CO
HO
CHOH3CO
HO
NO2
HS
H2N
1 2, 80%
Microwave
3-4 min.
solvent free
HNO3
HOAc
NO2
OCH3
Ac2O, Et3N
DCM
1h
5, 80%
OCH3
S
N
NH
O
H3C
OAc
LiOH
6, 95%
OCH3
S
N
NH
O
H3C
OH
H2O
MeOH
30 m
1h
EtOH
6 h
 
Scheme 1: Synthesis of the target compounds 
 
Reduction of nitro group to amino group was 
optimized by using some classic methods, table 1. 
All entries were carried out up to 20 hours and 
monitored with thin layer chromatography (TLC). In 
the first entry, Na2S2O4/NaOH reagents were used 
[11]. Unfortunately, as soon as the reagents added, 
the reaction solution turned black due to the reason 
that in the basic condition, free aniline 3’ was 
formed and oxidized by oxygen in the air, scheme 2. 
Nevertheless, there was a question: why was amine 
3’ oxidized easily? Because the benzene ring 
contains 4 donating electron groups –OCH3, -O
-
,       
-NH2 and benzo[d]thiazole ring [12] that raises the 
electron density on the benzene ring, consequently, 
it is oxidized quickly called the aniline black. 
 
OH
S
N
3 NH2
ONa
OCH3
S
N
3'
NO2
OCH3
Na2S2O4
NaOH
O2
(air)
black solution
 
Scheme 2: Aniline black observation 
 
This result helps us think about the use of acidic 
conditions [13] and save the amine as a salt form. 
Hence, the entries 2-7 were treated with either 
concentrated HCl or NH4Cl in water and in ethanol. It 
was found thaethanol was better solvent than water 
since ethanol could dissolve substrates well but could 
not dissolve salt form 4. In comparison of Zn with Fe, 
both gave good yields, but it was difficult to separate 
the unreacted Zn out of the mixture, while iron could 
be attached to the stirring bar so the unreacted iron 
was removed just by washing the stirring bar simply. 
Finally, the salt 4 was easily filtered and dried for 
next step without further purification. Surprisingly, 
Fe/NH4Cl [14] did not work in this case because the 
acidity of ammonium chloride is weaker than the salt 
form 4 and the free amine was formed then oxidized 
  
VJC, 55(4), 2017  Duong Quoc Hoan et al. 
436 
immediately resulting in black solution as observed. 
All entries taken place in water were slowly or no 
reaction due to small solubility of substrates in water.   
 
Table 1: Reduction optimization results 
Entry Reagent Solvent Time (h) Observation Yield (%) 
1 Na2S2O4/NaOH H2O 0.5, reflux Black solution 0 
2 Zn/con. HCl H2O 14, reflux Yellow solution 75 
3 Zn/con. HCl C2H5OH 7, reflux Yellow solid 95 (impure) 
4 Fe/NH4Cl H2O 18, 50 °C Black solution 0 
5 Fe/NH4Cl C2H5OH 20, 50 °C Black solution 0 
6 Fe/con. HCl H2O 12, reflux Yellow solution 70 
7 Fe/con. HCl C2H5OH 7, reflux Yellow solid 95 (pure) 
 
As there was an amine salt 4 in hand, it was treated 
with acetic anhydride to form N,O-diacetyl 
compound 5 in 80 % yield. Then N,O-diacetyl 
compound 5 was hydrolyzed in methanol and LiOH 
giving N-acetyl amide 6 in 95 % yield. 
 
3.2. Structure determination 
 
Nitrovanillin 2 was checked for melting point, and it 
matched with the previous report [9, 10]. Because 
compounds 3, 4, 5 and 6 are new, so they were 
recorded for IR, MS and NMR spectra to determine 
their structures. Spectroscopic data were analyzed 
carefully [15]. First, IR spectrum of nitro compound 
3 did not show the vibration of carbonyl group of 
vanillin that indicated cyclization of 
benzo[d]thiazole occurred. IR of compound 4 
showed broad band of N-H bond in range 3100-2500 
cm
-1
 that was for N-H vibration in the ammonium-
like form. IR spectrum of compound 5 showed two 
signals of carbonyl groups at 1735 and 1692 cm
-1
, 
that indicated two acetyl groups must be in the 
structure of N,O-diacetyl compound 5. IR spectrum 
of N-acetyl amide 6 showed a band at 1690 cm
-1
 and 
vibration of N-H amide at 3325 cm
-1
 and overlapped 
with vibration of O-H bond. Next, 
1
H NMR 
spectrum of nitroaromatic compound 3 and salt 4 
showed 6 protons of aromatic rings and 3 protons of 
methoxy group; however, 
1
H NMR spectra of both 
the nitroaromatic compound 3 and the salt 4 did not 
show a proton of OH group since it appeared in the 
block of solvent peaks. 
13
C NMR spectrum of 
compound 4 showed 14 peaks for 14 carbon atoms. 
Meanwhile, 
1
H NMR and 
13
C NMR of N,O-diacetyl 
compound 5 showed two signals at  2.33 ppm (s, 
3H) and 2.14 ppm (s, 3H) and 2 peaks in the weak 
field at 169.11 ppm and 167.98 ppm assigned for 
two carbonyl groups of acetyl amide and acetyl 
ester. Other two peaks at  23.85 ppm and  20.79 
ppm belonged to two methyl groups of these acetyl 
groups. After hydrolysis of N,O-diacetyl compound 
5 to obtain N-acetyl compound 6, 
1
H NMR and 
13
C 
NMR of N-acetyl compound 6 showed only a peak 
at  2.25 ppm for methyl of the acetyl amide 
associated with the peak at  25.50 ppm on the 13C 
NMR spectrum. 
 
 
Figure 2: A part of HMBC spectrum 
Then, in order to assign each carbon and 
hydrogen in the target product 6, HSQC and HMBC 
spectra were studied carefully. First, HSQC 
spectrum indicated cross-peaks of carbons bearing 
protons. Although, there were still some pairs of 
carbons or protons that were difficult to indentify 
such as C7/C15; C3/C4; C1/C6; C9/C13; C10/C12; 
H4/H3; H9/H13; H2/H5 and NH/OH, HMBC 
spectrum distinguished all. For example, C7 had 
HMBC cross-peaks with H9 and H13 but C15 did 
not. In addition, C15 had an HMBC cross-peak with 
H15, on the other hand, C7 hadn’t got further peaks. 
  
VJC, 55(4), 2017  Preparation of some new…   
437 
The most difficult assignment was identification of 
C13/C19 and H13/H9. Fortunately, it was easily to 
find H14 that had an HMBC cross-peak with H9. 
Therefore, H13 and C13 were identified and so on. 
Other assignments were shown in the figure 2.   
Finally, compounds 3, 4, 5 and 6 were recorded 
for mass spectroscopy. MS spectrum of compound 3 
indicated the first fragment was NO [M-30+H] at 
m/z 273 au, [M-30-H] at m/z 271 au that matched 
with calculated. MS spectra of compounds 4, 5 and 6 
also confirmed the expected structure as shown in 
the experimental section. 
 
4. CONCLUSION 
 
Four new benzo[d]thiazole derivatives (3, 4, 5 and 
6) were successfully synthesized in high yield. Fe 
powder and concentrated HCl in ethanol was the 
best condition for converting nitro group to amine 
group in our case. All reactions worked under simple 
conditions and gave excellent yields. Structures of 
compounds nitroaromatic 3, salt 4, N,O-diacetyl 5 
and N-acetyl 6 were confirmed with IR, NMR and 
MS analyses.  
 
Acknowledgements. This research is supported by 
Hanoi National University of Education (HNUE) 
under the project code SPHN16-25TT. 
 
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Corresponding author: Duong Quoc Hoan  
Department of Chemistry, Hanoi National University of Education 
No. 136, Xuan Thuy Str., Cau Giay Dist., Ha Noi 
E-mail: hoandq@hnue.edu.vn; Telephone: 0986778213.  


Preparation of some new benzo[d]thiazole derivatives

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