One-Pot, Borax-mediated synthesis of structurally diverse N, S-heterocycles in water

Article abstract of DOI:10.1016/j.tetlet.2021.153159

Herein, a borax–mediated convenient and efficient strategy for the synthesis of prominent structurally diverse N, S-heterocycles such as quinazolin-4(3H)-one, benzothiadiazine 1,1-dioxide, benzothioazole, and benzoxazoles from readily available 2-aminobenzamide/2-aminobenzenesulfonamide/2-aminothiophenol/2-aminophenol with α,α,α-trihalotoluenes at 100 ℃ in water is elaborated. Upon using aldehydes instead of α,α,α-trihalotoluenes, the reactions proceed through domino fashion under the catalytic effect borax to yield 2,3-dihydroquinazolin-4(1H)-one, 3,4-dihydrothiadiazine 1,1-dioxide, and benzothiazoles in one-pot at 60 ℃. The advantages of this protocol are practical simplicity, large substrate scope, moderate to excellent yields, and the use of water as the solvent.

Full text of DOI:10.1016/j.tetlet.2021.153159

Tetrahedron Letters xxx (xxxx) xxx
Contents lists available at ScienceDirect
Tetrahedron Letters
journal homepage: www.elsevier.com/locate/tetlet
One-Pot, Borax-mediated synthesis of structurally diverse N,
S-heterocycles in water
⇑
Mugada Sugunakara Rao, Sahid Hussain
Department of Chemistry, Indian Institute of Technology Patna, Bihta, Patna 801106, India
a r t i c l e i n f o
a b s t r a c t
Article history:
Herein, a borax–mediated convenient and efficient strategy for the synthesis of prominent structurally
diverse N, S-heterocycles such as quinazolin-4(3H)-one, benzothiadiazine 1,1-dioxide, benzothioazole,
and benzoxazoles from readily available 2-aminobenzamide/2-aminobenzenesulfonamide/2-aminothio-
Received 18 March 2021
Revised 4 May 2021
Accepted 5 May 2021
Available online xxxx
phenol/2-aminophenol with
a,a,a-trihalotoluenes at 100 ℃ in water is elaborated. Upon using aldehydes
instead of -trihalotoluenes, the reactions proceed through domino fashion under the catalytic effect
a,a,a
borax to yield 2,3-dihydroquinazolin-4(1H)-one, 3,4-dihydrothiadiazine 1,1-dioxide, and benzothiazoles
in one-pot at 60 ℃. The advantages of this protocol are practical simplicity, large substrate scope, mod-
erate to excellent yields, and the use of water as the solvent.
Keywords:
Borax
Quinazolin-4(3H)-one
Benzothiadiazine 1
1-Dioxide
Ó 2021 Elsevier Ltd. All rights reserved.
Benzothioazole
aaa-Trihalotoluene
Introduction
as benzyl amines [14], benzyl halides [15], methyl arenes [16],
benzoyl chlorides [17], aryl ketones [18], CO/aryl halides [19],
Nitrogen-Sulfur heterocyclic compounds have raised the great
interest of organic chemists for several decades, due to their innu-
merable importance in natural products, advanced materials, and
designing bioactive molecules used for various pharmaceutical
necessities [1]. Specifically, quinazolinones, benzothiadiazole-1,1-
dioxide, and its polycyclic motifs are the very important building
block of heterocycles because of their biological and pharmaceuti-
cal activities (Fig. 1) including antibacterial [2], antiviral [3], anti-
malarial [4], anticancer [5], antihypertensive [6], antitubercular
[7], and they also act as inhibitors of various enzymes [8]. Addi-
tionally, quinazolinones are acting as ligands for AMPA and benzo-
diazepine receptors in the CNS organism or as DNA binders [9].
Owing to its long-standing recognition, chemists paid a great
deal of attention to find a straightforward synthetic approach to
quinazolin-4(3H)-one, and benzothiadiazine1,1-dioxides [10]. A
literature survey reveals numerous studies on synthetic approach
to quinazoline-4(3H)-one and benzothiadiazine1,1-dioxides from
2-aminobenzamide/2-aminobenzenesulfonamide with simple aryl
precursors (aldehydes [11], benzyl alcohols [12], and benzoic acids
[13]) used under metal or metal-free conditions. In particular,
quinazolin-4(3H)-ones can also be prepared by the condensation
reactions of 2-aminobenzamide with carbonyl equivalents, such
and aryl halides with isocyanides insertion [20] (Scheme 1). Many
of these methods, some of which have drawbacks, such as low or
varying yields and time, use of costly chemicals, less substrate tol-
erance, use of coupling agents or metal catalysts, frequently
require harsh reaction conditions and time-consuming work-up
procedures. Therefore, a simple and an atom economy approach
for the synthesis of quinazolinones and benzothiadiazine1,1-diox-
ides from easily available starting materials is still desirable.
Borax (Na2B4O7) has been recently advanced as a mild, environ-
mentally benign, non-toxic, and naturally occurring substance that
provides hydroxyl anion (Brønsted base) and boric acid (Lewis
acid) in aqueous solution (pH value 9.5). It has shown chemo,
and stereoselectivity in many organic transformations such as
Nef reaction, substitution, condensation, addition (including het-
ero-Michael reaction), etc. [21]. On the other side, the literature
survey indicated that the groups of a,a,a-trihalotoluenes have been
used to prepare a variety of heterocycles with di-nucleophiles [22].
Our ongoing study on the use of borax as catalyst and reagent in a
variety of reactions to synthesize the potentially bioactive nitrogen
and sulfur heterocycles is still on [21f-h].
In the current work, we have developed a new synthetic proto-
col in water for the synthesis of quinazolin-4(3H)-one/benzothia-
diazine 1,1-dioxides/benzothiazole/benzoxazoles from a simple
and easily accessible 2-aminobenzamide/2-aminobenzenesulfon-
⇑
Corresponding author.
E-mail address: sahid@iitp.ac.in (S. Hussain).
amide/2-aminothiophenol/2-aminophenol and
a,a,a-trihalotolue-
https://doi.org/10.1016/j.tetlet.2021.153159
0040-4039/Ó 2021 Elsevier Ltd. All rights reserved.
Please cite this article as: Mugada Sugunakara Rao and S. Hussain, One-Pot, Borax-mediated synthesis of structurally diverse N, S-heterocycles in water,
Tetrahedron Letters, https://doi.org/10.1016/j.tetlet.2021.153159

Mugada Sugunakara Rao and S. Hussain
Tetrahedron Letters xxx (xxxx) xxx
Fig. 1. Examples of biologically and pharmaceutically important N, S-heterocycles.
Scheme 1. Strategies for the synthesis of quinazoline-4(3H)-one and benzothiadiazine1,1-dioxides.
2

Mugada Sugunakara Rao and S. Hussain
Tetrahedron Letters xxx (xxxx) xxx
nes, and also one-pot cascade synthesis of 2,3-dihydroquinazolin-4
(1H)-one/3,4-dihydrothiadiazine 1,1-dioxide/benzothiazoles from
2-aminobenzamide/2-aminobenzenesulfonamide/2-aminothio-
phenol and aldehydes in the presence of borax (Scheme 1).
2-aminobenzenesulfonamide was used. The reactions proceed
smoothly and the results are in Table 2. It is noteworthy that sub-
stituted benzothiadiazine 1,1-dioxides derivatives could be pre-
pared in good yields (Table 2, 5a-c. Furthermore, to demonstrate
the utility of the current method, benzothiazole, and benzoxazole
derivatives were synthesized under optimal conditions using 2-
aminothiophenol and 2-aminophenol in place of 2-aminobenza-
mide. The corresponding products were obtained in 71–85% yields
(Table 2, 7a-c, 9a-c).
Results and discussion
For the initial study, the synthesis of quinazolin-4(3H)-one (3a)
was chosen as a model reaction and optimization was done with 2-
aminobenzamide (1a) and a,a,a-trichlorotoluene (2a), in the pres-
After successful accomplishment of the reaction of
a,a,a-
trichlorotoluenes, and 2-aminobenzamide, we noted the impor-
tance of 2,3-dihydroquinazolin-4(1H)-ones [23], which can also
be prepared from 2-aminobenzamide. In recent years, several
methods have been reported for the preparation of 2,3-dihydro-
quinazolin-4(1H)-ones using a variety of homogeneous or hetero-
geneous catalysts such as I2, ZrCl4, SbCl3, cyanuric chloride, TFA,
morpholinoethanesulfonic acid, B(C6F5)3, Y(OTf)3, [Al(H2PO4)3],
ence of 3 equivalent of borax and the optimized conditions are
shown in Table 1. We observed when solvents either aprotic sol-
vents such as acetonitrile and toluene or protic solvents ethanol
and methanol were used in the reaction, only the desired product
3a was obtained in fewer yields (Table 1, entries 1–4). It is gratify-
ing, while the reaction conducted in water gives 68% of 3a was
obtained at 80 °C for 14 h (Table 1, entry 5). Further, increasing
the temperature to 100 °C, the amount of borax to 4 equivalent,
and time, the reaction yield is increased to 78% (Table 1, entry 6).
A further increase and decrease in the amount of borax were opti-
mized and the results are summarized in Table 1 (entries, 7–9). The
reaction proceeds in a trace amount at room temperature and the
reaction did not proceed at all in the absence of borax (Table 1,
entries 10 and 11). The formation of compound 3a was confirmed
by comparing FT-IR, 1H, and 13C NMR spectroscopic data with liter-
ature data. The optimal reaction conditions were, therefore,
ZrO2–Al2O3, L-proline nitrate, amberlyst-15, a-chymotrypsin, gra-
phene oxide, heteropoly acids, ionic liquids, b-cyclodextrinSO3H,
PEG-400 and magnetic nanoparticles [24]. The catalysts that have
been used are either expensive or relatively more toxic. Because
of the above, we further stretched the use of borax for the prepara-
tion of 2,3-dihydroquinazolinones, which could be produced by
simply replacing a,a,a-trichlorotoluenes with aldehydes as shown
in Scheme 2. The 20 mol% borax is sufficient to complete the reac-
tion with high yields at 60 °C. It was noticed that the methodology
is tolerable with a variety of substituents on the substrate. The
observed corresponding products in each result were obtained in
high yields and short reaction time of 2–3 h (Table 3). The sub-
stituent on the aromatic aldehydes showed slightly different
effects on the yields. The reactions of aromatic aldehydes with
electron-withdrawing groups afforded little better yields of prod-
ucts than those with the electron-donating groups (Table 2, 11a-
g). Moreover, the reactions of heterocyclic aldehydes with thio-
phene also gave a good yield (Table 2, 11h). To further extend
the scope of the reaction, a few substituted 2-aminobenzamides
(5-methyl and 5-chloro) were used to carry out reaction with alde-
hydes. It also gave 87–89% yields (Table 2, 11i and 11j). Unfortu-
nately, propionaldehyde and acetophenone failed to produce the
desired product (Table 2, 11k and 11l).
achieved with 2-aminobenzamide (1a) (0.3 mmol), a,a,a-trichloro-
toluene (2a) (0.36 mmol) and 4 equiv of borax in water at 100 °C
for 14 h (Table 1, entry 6).
The protocol’s applicability was checked under optimal condi-
tions. As shown in Table 2, the scope of the reaction involving
a,
a,a
-trichlorotoluene was first investigated. The reactions of a,a,a-
trichlorotoluene substituted with electron-withdrawing groups
(F, Cl) at various positions in the aryl ring furnished the corre-
sponding products in moderate to satisfactory yields (Table 2,
60–74%, 3b-3d). Substituted 2-aminobenzamide with electron-
withdrawing and electron-donating groups at the 5-position, such
as fluoro, chloro, nitro, and methyl groups, is then investigated.
Electron-donating groups were found to yield products better than
electron-withdrawing groups respectively (Table 2, 69–75%, 3e-
3h).
Later, the above reaction conditions were then applied towards
the synthesis of 3,4-dihydrobenzothiadiazine 1,1-dioxides
(Table 3). 2-aminobenzenesulfonamide reacts with benzaldehyde
to produce 3,4-dihydrobenzothiadiazine 1,1-dioxide 12a in 87%
After the successful conversion to the desired product, the
scope of this reaction was further extended to the synthesis of
benzothiadiazine 1,1-dioxides. Instead of 2-aminobenzamide,
Table 1
Optimization of reaction conditions.a
Entry
Reagent
Solvent
Temp. (°C)
Time (hours)
Yield (%)a
1.
2.
3.
4
5.
6.
7.
8.
9.
Borax (3equiv)
Borax (3 equiv)
Borax (3 equiv)
Borax (3 equiv)
Borax (3 equiv)
Borax (4 equiv)
Borax (5 equiv)
Borax (2 equiv)
Borax (1 equiv)
Borax (4 equiv)
–
CH3CN
Toluene
EtOH
MeOH
H2O
H2O
H2O
H2O
H2O
80
80
80
60
14
14
14
14
14
14
14
14
14
14
16
25
10
45
34
68
78
79
51
22
Trace
–
80
100
100
100
100
r.t
10.
11.
H2O
H2O
100
aIsolated yields.
3

Mugada Sugunakara Rao and S. Hussain
Tetrahedron Letters xxx (xxxx) xxx
Table 2
Substrate scope.
CCl3
Y
N
X
Nu
NH
Borax, 4 equiv
H2O, 100 °C
Borax, 4 equiv
H2O, 100 °C
+
R2
N
R1
R1
NH2
R2
R2
7, 9
2
3, 5
Nu = CONH2 (1), SO2NH2 (4),
SH (6), OH (8)
X = S, O
Y = CO, SO2
S
N
O
X
N
Me
X = F, 7b, 76%, 10 h
X = Cl, 7c, 81%, 10 h
9c, 71%, 10 h
Scheme 2. Synthesis of 2,3-dihydroquinazolinone, 3,4-dihydrobenzothiadiazine 1,1-dioxide and benzothiazoles.
yield. Whereas halo, nitro, methoxy-substituted benzaldehyde, and
2-napthaldehydes offered yields ranging from 80 to 90% (12b-f). As
well as heterocyclic 2-thiophene carboxaldehyde furnished pro-
duct (12g) in 85% yield.
All the compounds were purified by column chromatography.
The structure of all products was confirmed by comparing spectro-
scopic data with literature values. The structure of 3-(4-methoxy-
phenyl)-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine
1,1-dioxide
Further, the reaction is applied to synthesize benzothiazole
derivatives under a similar condition from the reaction of 2-
aminothiophenol with aromatic aldehydes. Aldehydes with
different substituents like p-Cl, m-NO2, p-OMe or 2-thiophene
carboxaldehyde afforded the expected products in 80–87% yields
(Table 3, 7a, and 7c-f).
dimethyl sulfoxide mono solvate (12eꢀDMSO) was unambiguously
proved by X-ray single-crystal studies (Fig. 2).
A probable mechanism for the synthesis of quinazolin-4(1H)-
one 3a and 2,3-dihydroquinazolinones 11a is illustrated in
Scheme 3 [21,22]. The reaction seems to be initially occurring by
the partial hydrolysis
a,a,a
-trichlorotoluene by OH– (produced
4

Mugada Sugunakara Rao and S. Hussain
Tetrahedron Letters xxx (xxxx) xxx
Table 3
Substrate scope.
O
NH
NO2
N
H
11e, 93%, 3h
O
O
O
O
Me
Cl
NH
CH3
NH
NH
NH
N
H
N
H
N
H
N
H
11k, 0%, 6 h
11i, 89%, 3h
11j, 87%, 3h
11l, 0%, 6 h
from aqueous borax) leads to the formation of imine (A) from 2-
aminobenzamide. Then, the presence of B(OH)3 and OH– in the
reaction medium help in intramolecular cyclization through (B)
to the desired product 3a. Whereas, for the synthesis of 2,3-dihy-
droquinazolin-4(1H)-one (11a), the formation of imine takes place
5

Mugada Sugunakara Rao and S. Hussain
Tetrahedron Letters xxx (xxxx) xxx
aminobenzenesulfonamide/2-aminothiophenol at 60 ℃. Moderate
to high yields of the desired products and green solvents such as
water are important features of this protocol.
Experimental section
General procedure for the synthesis of quinazolin-4(3H)-one/
benzothiadiazine 1,1-dioxides/benzothiazole/benzoxazoles (3, 5, 7, and
9)
2-Aminobenzamide/2-aminobenzenesulfonamide/2-aminoth-
iophenol/2-aminophenol (0.3 mmol),
a,a,a-trichlorotoluene
(0.36 mmol), and borax (4 equiv) were taken in a 50 ml round bot-
tom flask, and the reaction mixture was stirred in H2O (3 ml) at 100
℃ for a period of the time till the completion of the reaction (mon-
itored by TLC). After completion of the reaction, it was extracted
with ethyl acetate. The combined organic layers were washed with
water and brine, dried over sodium sulfate, and concentrated
under reduced pressure. The crude product was purified by column
chromatography to give the desired product. All compounds were
well characterized by FT-IR, 1H, 13C NMR, and melting point
analysis.
Fig. 2. Single-Crystal XRD structure of 12e (CCDC 2063586).
initially (A’), which cyclizes in the presence of borax to give the
final product (Scheme 2b).
Conclusions
General procedure for the synthesis of 2,3-dihydroquinazolinones/3,4-
dihydrobenzothiadiazine 1,1-dioxide/benzothiazoles (11, 12, and 7)
In summary, we have developed a convenient and straightfor-
ward borax-mediated synthetic protocol for the synthesis of bio-
logically relevant quinazoline-4(3H)-one, benzothiadiazine 1,1-
dioxide, benzothiazole, and benzoxazoles from simple and easily
2-Aminobenzamide/2-aminobenzenesulfonamide/2-aminoth-
iophenol (0.3 mmol), aldehyde (0.3 mmol), and borax (20 mol %)
were taken in a 50 ml round bottom flask, and the reaction mixture
was stirred in H2O (2 ml) at 60 ℃ for a period of time till the com-
pletion of the reaction (monitored by TLC). After completion of the
reaction, it was extracted with ethyl acetate. The combined organic
layers were washed with water and brine, dried over sodium sul-
fate, and concentrated under reduced pressure. The crude product
was purified by column chromatography to give the desired
accessible
aminothiophenol/2-aminophenol and
2-aminobenzamide/2-aminobenzenesulfonamide/2-
-trihalotoluenes at 100
a,a,a
℃. In addition, one-pot, borax catalyzed a domino strategy for the
synthesis of 2,3-dihydroquinazolin-4(1H)-one, 3,4-dihydrothiadi-
azine 1,1-dioxide, and benzothiazoles from both aromatic and het-
ero-aromatic
aldehydes
with
2-aminobenzamide/2-
Scheme 3. Proposed mechanism for the synthesis of quinazoline-4(3H)-one (a) and 2,3-dihydroquinazolinones (b).
6

Mugada Sugunakara Rao and S. Hussain
Tetrahedron Letters xxx (xxxx) xxx
product. All compounds were well characterized by FT-IR, 1H, 13C
NMR, and melting point analysis.
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Declaration of Competing Interest
The authors declare that they have no known competing finan-
cial interests or personal relationships that could have appeared
to influence the work reported in this paper.
Acknowledgments
M.S. Rao is thankful to IIT Patna for his research fellowship and
research support. SAIF-IIT Patna is gratefully acknowledged for
providing a Single Crystal-XRD facility.
Appendix A. Supplementary data
Supplementary data to this article can be found online at
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