Tetrahedron Letters 104 (2022) 154020

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Tetrahedron Letters
journal homepage: www.elsevier.com/locate/tetlet

An efficient, surfactant mediated Biginelli condensation for the one pot

synthesis of dihydropyrimidine derivatives
Deboshikha Bhattacharjee, Bekington Myrboh ⇑
Centre for Advanced Studies in Chemistry, Department of Chemistry, North-Eastern Hill University, Mawlai, Shillong 793022, India

a r t i c l e i n f o a b s t r a c t

Article history: Sodium dodecyl sulfate (SDS) has been demonstrated as an efficient surfactant mediated catalyst for the
Received 2 June 2022 synthesis of dihydropyrimidinone derivatives by the Biginelli condensation of aldehydes, b-dicarbonyls,
Revised 6 July 2022 and urea/thiourea. The one-pot three component reaction was accomplished in aqueous micellar media
Accepted 11 July 2022
affording excellent yield of the products. The reaction being facile and simple is also supplemented with
Available online 14 July 2022
merits like eco-friendly catalyst, aqueous reaction media and non-chromatographic methods of purifica-
tion. The versatility of this method was examined with various substituted aldehydes and has proved to
be proficient with satisfactory results.
Ó 2022 Elsevier Ltd. All rights reserved.

Introduction proposed but unfortunately, the synthesis of 3,4-dihydropyrim-

Multi-component reactions have emerged as an important pro-
tocol in recent times for the synthesis of biologically important
scaffolds. One of the important scaffolds known is 3,4-dihydropy-
rimidin-2(1H)-ones (DHPM), the derivatives of which is well
known to exhibit significant therapeutic and pharmacological
properties such as antiviral, antitumour, antibacterial, and antiin-
flammatory. [1] In addition to this, some of DHMPS have been
employed as calcium channel blockers, a-1a-antagonists and neu-
ropeptide Y(NPY) antagonists. [2] To name a few important
DHMPS, Monastrol exhibits important biological property thereby
blocking mitosis by specifically inhibiting the motor activity of the
mitotic kinesin Eg5 and is a pilot molecule for the advancement of
novel anticancer drugs, (R)-SQ 32926, SQ 32547, SWO2 also known
to be antihypertensive agent with potent oral activity and Mon-97
shows promising anticancer activity (Fig.1). [3] Several alkaloids
obtained from marine sources have been also found to possess
the dihydropyrimidine core unit. Most noteworthy among these
are the batzelladine alkaloids, which were found to be potent
HIVgp-120-CD4 inhibitors. [4].
The earliest attempt to synthesize the 3,4-dihydropyrimidin-2
(1H)-ones was reported by Pietro Biginelli in 1893, [5] where he
performed the three-component cyclocondensation reaction of
ethyl acetoacetate, benzaldehyde and urea under Bronsted acid
catalysis. However, this reaction has drawbacks like harsh condi-
tions, high reaction time and low yields. Since the early days of
the discovery of this reaction several reaction routes have been
⇑ Corresponding author.
E-mail address: bmyrboh@nehu.ac.in (B. Myrboh).
idin-2(1H)-ones often provides generally low to moderate yields.
Therefore, the development more efficient protocols for the syn-
thesis the pharmacologically important DHMPs still remains rele-
vant amongst researchers.
A number of catalysts have been employed for the Biginelli
reaction which includes both homogenous and heterogeneous cat-
alysts like p-toluene sulfonic acid, [6] SiO2-polyphosphoric acid
(SiO2-PPA), [7] boric acid, [8] HCl/FeCl3, [9] polyvinyl sulfonic acid,
[10] graphite, [11] L-proline, [12] silica sulfuric acid, [13] zeolite,
[14] sulphated tungstate, [15] xanthan sulfuric acid, [16] montmo-
rillonite KSF, [17] sulphated silica tungstic acid, [18] PPF–SO3H,
[19] Al(HSO4)3, [20] vanadium(III) chloride, [21] bio glycerol-based
sulfonic acid functionalized carbon catalyst. [22] Generally classi-
cal methods like heating, microwave and ultrasound irradiations
have been used for the synthesis 3,4-Dihydropyrimidin-2(1H)-
ones/thiones under different catalytic condition. [23] Other impro-
vised catalysts include ionic liquids, [24] heteropolyacids, [25]
nanomaterials [26–28], sulphated polyborate [29] which have
been also utilised for the synthesis of these important heterocycles.
Although a number of improved methods have been developed,
most of them however suffer from drawbacks such as cumbersome
synthesis of catalysts, use of corrosive/toxic metal-based catalysts,
volatile organic solvents, unsatisfactory yields, high cost, longer
reaction times and harsh reaction conditions. Thus, there is still
scope for the development of new and more efficient methods
for the synthesis of these important heterocycles keeping in mind
the green principle of chemistry.
The thrust for clean, green synthetic processes requires atom
economy, minimal waste generation, environmentally benign
reagents & solvents as the prime ingredients and water serves as

https://doi.org/10.1016/j.tetlet.2022.154020
0040-4039/Ó 2022 Elsevier Ltd. All rights reserved.
D. Bhattacharjee and B. Myrboh
Fig. 1. Pharmacologically important 3,4-dihydropyrimidin-2(1H)-ones/thiones.
the most preferred solvent whenever possible. [30] The low solu-
bility of organic reagents and the instability of the majority of cat-
alysts in water mediated reaction is a concern. But in recent time,
many surfactants have been used as phase transfer catalysts in sev-
eral organic reactions having unique capabilities to dissolve both
organic and aqueous solutions to enhance the rate of the reaction.
[31] The anionic surfactant sodium dodecyl sulphate (SDS), shows
the catalytic activity almost equal with Brønsted acids, such as
sodium hydrosulphate or p-toluene sulfonic acid. Moreover, its cat-
alytic activity is also known be greater than that of most Lewis
acids [32] and therefore, SDS has been employed as catalyst in a
variety of reaction schemes. [32–33] In the reaction medium SDS
forms micelles in water and can both solubilise the organic com-
pounds and catalyse the reaction thus increasing the energy
efficiency.
Therefore, in our continuous quest [34] for more efficient green
reaction protocols for the synthesis of the biologically important
3,4-dihydropyrimidin-2(1H)-ones/thiones, the employment of
SDS an eco-friendly and cheap catalytic system for the one-pot
three-component synthesis of 3,4-dihydropyrimidin-2(1H)-ones/
thiones derivatives in aqueous medium was explored.
Results and discussion
As a part of our effort towards the development of environmen-
tally benign synthetic methods for multi-component reactions
(MCRs) to synthesize various biologically important heterocyclic
compounds, we have developed an efficient synthesis of 3,4-dihy-
dropyrimidin-2(1H)-ones/thiones derivatives (6/7) using SDS in
water at 60 °C via the condensation of aldehyde (1), ethyl acetoac-
etate (2)/methyl acetoacetate (3), and urea/thiourea (4/5)
(Scheme 1).
In our initial attempt to synthesize the 3,4-dihydropyrimidin-2
(1H)-ones/thiones derivatives, we selected the model reaction of
4 Chloro benzaldehyde (1a) (2.0 mmol), urea (4) (3.0 mmol) and
ethyl acetoacetate (3) (2.1 mmol) to yield ethyl 4-(4-chlorophe-
nyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
2
Tetrahedron Letters 104 (2022) 154020
(6a). To investigate the effect of catalyst, the model reaction was
carried out in absence of any catalyst which resulted in no product
formation even after 18 h. The reaction was further heated for 24 h
which resulted in only trace amount of the product. In the next
attempt we employed SDS a surfactant as catalyst in the model
reaction at room temperature in water which resulted in very less
product formation even after stirring for 12 h. The reaction was
then heated to 60 °C which furnished the desired product in a spec-
ulated time of 4 h. Encouraged by this result, we carried out the
reaction of 4 methyl benzaldehyde (1 h) (2.0 mmol), thiourea (5)
(3.0 mmol) and ethyl acetoacetate (2) (2.1 mmol) under identical
conditions. Upon stirring the reaction at 60 °C excellent yield
(92 %) of the product (6 h) was obtained in little longer time
(5 h). The efficacy of this method was further enhanced when
Monastrol (6 k), a biologically active molecule has been success-
fully synthesized. The structure of the compounds formed were
confirmed by 1H & 13C NMR, Mass and IR analyses.
In order to evaluate the catalyst loading, the model reaction was
carried out at different catalyst loading, viz. no catalyst, 05 mol%,
10 mol%, 15 mol%, 20 mol%, and 25 mol% of SDS in water at
60 °C. Except in case of no catalyst condition the reaction worked
in all cases. In case of 5 mol% to 15 mol% catalyst loadings the
expected product formation was only up to 55 % upon stirring
for 4 h. To our delight, it was observed that when catalyst loadings
was increased to 20 mol% and 25 mol% the reaction yielded 85 %
and 91 % yield respectively in similar time of 4 h. Interestingly,
enhancement of catalyst loading to 30 mol% did not result in
reduction of the reaction time appreciably and gave almost similar
yields to that of optimum catalyst loading (25 mol %) in 4 h (Fig. 2).
The efficiency of nonionic surfactant PEG-600, Tween-80 and
cationic surfactant TBAB, CTAB were also screened in order to eval-
uate and compare the catalytic activity for the three-component
model reaction in water. It is evident from Fig. 3 TBAB and CTAB
was also efficient enough to catalyze the reaction to yield 69 %
and 75 % respectively whereas PEG-600 and Tween-80 gave poor
result under similar reaction condition yielding only 42 % and
D. Bhattacharjee and B. Myrboh
Scheme 1. SDS catalysed synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones derivatives.
Fig. 2. Effect of Catalyst loading and temperature on the yield of the product.
Fig. 3. Effect of surfactant on the yield of the product.
35 % respectively proving SDS as the best surfactant for the men-
tioned reaction yielding 91 % of the desired product.
The effect of solvent was then investigated by carrying out the
model reaction in different solvents like DCM, THF, chloroform,
DMF, H2O and in EtOH:H2O (1:1) ratio at fixed catalyst loading
(25 mol%). It was observed that the reaction was efficient in protic
solvents like EtOH, H2O, EtOH:H2O, whereas in other solvent the
reaction proceeded sluggishly (Fig. 4), thus confirming water as
the best suited solvent for the micelle formation. Micelles can be
used to promote multi-component reactions by taking advantage
of the confinement effect as well as of the presence of certain func-
tional groups on the surface of the aggregates to improve the yield
and reaction time.
The catalyst recyclability was investigated for the model reac-
tion (Fig. 5). Catalyst was recovered from the reaction mixture by
3
Tetrahedron Letters 104 (2022) 154020
Fig. 4. Effect of solvent on the yield of the product.
Fig. 5. Recyclability of the catalyst.
simple workup where the catalyst was retained in the aqueous
layer leaving behind the product in organic layer. The regenerated
catalyst in aqueous solution was then reused for the same reaction
and it was observed the efficiency of catalyst did not change appre-
ciably even after using for 4 consecutive times for the model
reaction.
After the optimization of the reaction parameters such as cata-
lyst, catalyst loading and solvent, the efficiency of the optimised
protocol was tested for a number of aromatic aldehydes having
varying substituent. In each case the reaction proceeded smoothly
at optimum reaction condition to give the desired product in mod-
erate to excellent yields. The presence of electron withdrawing or
releasing substituent in the ortho-, meta- and para-positions do
not appear to have any effect on the overall reaction yields
(Table 1). While in case of thiourea derivatives product formation
took longer time as compared to that of urea derivatives.
D. Bhattacharjee and B. Myrboh Tetrahedron Letters 104 (2022) 154020

Table 1
SDS catalysed synthesis of dihydropyrimidinones derivatives.

Entry X Aldehyde Producta Time(hrs) Yieldb

1 O 6a 4 91

2 O 6b 4 89

3 O 6c 4 87

4 O 6d 4 90

5 O 6e 4 92

6 S 6f 5 88

7 S 6g 5 85

8 S 6h 5 91

9 S 6i 5 89

10 S 6j 5 86

11 S 6k 5 85

Reaction Condition: aldehyde (2.0 mmol), ethyl acetoacetate (2.1 mmol), urea/thiourea (3.0 mmol), and SDS (25 mol %) at 60 °C.
a
Isolated yields.
b
Products were characterized by 1H & 13C NMR, Mass and IR analyses.

Likewise, almost identical results were obtained when methyl
acetoacetate (3) was replaced in place of ethyl acetoacetate (2)
and the three-component reaction with urea (4) and 4 Chloro ben-
zaldehyde (1a) was carried out in presence of 25 mol% of SDS in
water under similar condition. To study the scope of the reaction
thiourea (5) and varying substituted aldehydes (1) were employed.
The electrophilicity of the aldehydes resulting from the +I or I
effect of substituent on the phenyl ring did not much effected
the overall reaction yield in all the cases (Table 2). In case of
thiourea derivatives also gave very good yields under similar reac-
tion conditions, albeit taking longer times than their urea counter-
part. The products were successfully isolated and purified by
recrystallisation from ethanol without the use of chromatographic
method.
The catalytic property of SDS to accelerate the rate of reaction
can be explained as follows. In the above discussed reaction alde-
hyde, urea/thiourea, 1,3-diones condensed to produce dihydropy-
rimidinones derivatives which are hydrophobic in nature.
Surfactant forms micelle at a concentration above its CMC, and
the presence of additives decreases the CMC of ionic surfactants
to a large extent. This decrease in the CMC is attributed to the
counter-ion binding, which neutralize the charged headgroups of
the ionic micelles. It has also been reported that aromatic com-
pounds also reduce the CMC of ionic surfactants by residing at
the micellar interface. [35] The CMC of SDS in water is around
8 mM [36] and in the current reaction medium, wherein aromatic
aldehydes are present in addition to the other additives, the CMC of
SDS will be lowered as well. [37] Thus, in the micellar solution of
SDS the hydrophobic moieties escape away from water molecules
thereby encircling the micelle core of SDS. Moreover, the reactant
molecules are pushed by the water surrounding the micelle to
enter inside the hydrophobic core of the micelle and resulting

4
D. Bhattacharjee and B. Myrboh Tetrahedron Letters 104 (2022) 154020

Table 2
SDS catalysed synthesis of dihydropyrimidinones derivatives.

Entry X Aldehyde Producta Time(hrs) Yieldb

1 O 7a 4 93

2 O 7b 4 89

3 O 7c 4 85

4 O 7d 4 90

5 O 7e 4 91

6 S 7f 5 84

7 S 7g 5 92

8 S 7h 5 83

9 S 7i 5 93

10 S 7j 5 86

Reaction Condition: aldehyde (2.0 mmol), methyl acetoacetate (2.1 mmol), urea/thiourea (3.0 mmol), and SDS (25 mol %) at 60 °C.
a
Isolated yields.
b
Products were characterized by 1H & 13C NMR, Mass and IR analyses.

Fig. 6. Schematic representation of role of micellar SDS droplets on the reaction in aqueous media.

5
D. Bhattacharjee and B. Myrboh Tetrahedron Letters 104 (2022) 154020

Scheme 2. Plausible mechanism for the formation of dihydropyrimidinones/thione derivatives.

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