A highly efficient and green approach for the synthesis of pyrimido[4,5-b]quinolines using N,N-diethyl-N-sulfoethanaminium chloride

Article abstract of DOI:10.1515/znb-2020-0098

A highly efficient and green protocol for the synthesis of pyrimido[4,5-b]quinolines has been described. The one-pot multicomponent reaction of dimedone with arylaldehydes and 6-amino-1,3-dimethyluracil in the presence of N,N-diethyl-N-sulfoethanaminium c

Full text of DOI:10.1515/znb-2020-0098

Z. Naturforsch. 2021; 76(2)b: 85–90
Abdolkarim Zare* and Manije Dianat
A highly efficient and green approach for the
synthesis of pyrimido[4,5-b]quinolines using
N,N-diethyl-N-sulfoethanaminium chloride
https://doi.org/10.1515/znb-2020-0098
Received May 26, 2020; accepted October 5, 2020;
published online January 11, 2021
antifungal [11], antimalarial [12], and analgesic [13] prop-
erties. A significant class of heterocycles having uracil,
pyrimidine, and pyrimido-quinoline moieties in its struc-
ture is pyrimido[4,5-b]quinolines. They could be prepared
by the one-pot multi-component reaction of dimedone with
arylaldehydes and 6-amino-1,3-dimethyluracil. Some cat-
alysts have been reported for this transformation [14–22].
During the last decade, many research groups have
focused on the synthesis and utilization of ionic liquids
Abstract: A highly efficient and green protocol for the
synthesis of pyrimido[4,5-b]quinolines has been described.
The one-pot multicomponent reaction of dimedone with
arylaldehydes and 6-amino-1,3-dimethyluracil in the pres-
ence of N,N-diethyl-N-sulfoethanaminium chloride ([Et N–
3
SO H][Cl]) as an ionic liquid (IL) catalyst under solvent-free
3
(
ILs) in different scientific, pharmaceutical, and industrial
conditions afforded the mentioned compounds in high
yields and short reaction times. Our protocol is superior to
many of the reported protocols in terms of two or more of
these factors: the reaction times, yields, conditions (solvent-
free versus usage of organic solvents), temperature and
catalyst amount.
fields, because these organic salts have many exclusive
characteristics, consisting inter alia of good chemical and
thermal stabilities, low vapor pressure, wide liquid range,
ionic conductivity, and tunable chemical and physical
properties through variation of cation and anion. Some
applications of ILs include the use as electrolyte [23],
Keywords: 6-amino-1,3-dimethyluracil; acidic ionic liquid; simultaneous leaching and extraction of metallic ions [24],
multi-component reaction; N,N-diethyl-N-sulfoethanami- utilization as shale hydration inhibitors [25], preparation of
nium chloride ([Et N–SO H][Cl]); pyrimido[4,5-b]quino- homogeneous collagen and alginate hydrogels for skin
3
3
line; solvent-free.
dressing [26], usage in pharmaceutics and medicine [27],
and use as solvent and catalyst in organic synthesis
[
28–36].
Multi-component reactions (MCRs) are reactions
1
Introduction
wherein at least three different reactants connect together
to afford selectively a single product. They have several
merits relative to conventional multi-step reactions,
e.g., decreasing number of workups, simple operation,
decreasing energy consumption, minimizing purification
steps, and reduction of solvent consumption and waste
production. Thereby they qualify as being eco-friendly in
nature which contributes to their increasing significance in
organic synthesis, medicine discovery and material sci-
ence [37–40].
Solvent-free synthesis protocols have attracted special
attention as being superior to traditional methods with
regard to environmental and toxicity concerns, cost effec-
tiveness, and simplicity. It has been claimed that the best
solvent is no solvent [41–44].
Uracil, pyrimidine, quinoline, and pyrimido-quinoline are
scaffolds of many pharmaceutical and bioactive com-
pounds. Antimicrobial [1], antiviral [2], antioxidant [3], and
gonadotropin-releasing hormone receptor antagonist [4]
properties have been reported for the heterocycles in
which uracil and pyrimidine building blocks are present.
Quinoline-containing compounds have been utilized as
antitumor [5], DNA intercalating carrier [6], antihistaminic
[
7], and antimalarial [8] agents. Pyrimido-quinoline moi-
eties have been successfully integrated into heterocycles
having various medicinal activities, such as antiallergic
[
9], antimicrobial [1], anti-inflammatory [1], antitumor [10],
In this work, we tried to combine the advantages of
three green techniques, i.e., ionic-liquid catalysts, multi-
component reactions and solvent-free conditions, and
developed an effective ionic-liquid catalyst, namely N,N-
diethyl-N-sulfoethanaminium chloride ([Et N–SO H][Cl]),
*
Corresponding author: Abdolkarim Zare, Department of Chemistry,
Payame Noor University, P. O. Box 19395‐3697, Tehran, I. R. Iran,
E-mail: abdolkarimzare@pnu.ac.ir
Manije Dianat, Department of Chemistry, Payame Noor University,
P. O. Box 19395‐3697, Tehran, I. R. Iran
3
3

86
A. Zare and M. Dianat: Highly efficient synthesis of pyrimido[4,5-b]quinolines
for the preparation of pyrimido[4,5-b]quinolines via the Table : Effect of the catalyst quantity and temperature on the
model reaction.
one-pot multi-component reaction of dimedone with ary-
laldehydes and 6-amino-1,3-dimethyluracil under solvent-
free conditions
Entry
Catalyst
quantity (mol%)
Temp. (°C)
Time (min)
Yield (%)







–






















2
Results and discussion
a

a

In order to attain the most appropriate quantity of the catalyst
and the reaction temperature for the preparation of pyrimido


a

[4,5-b]quinolines, the one-pot multicomponent condensation
a
of dimedone (1 mmol) with 4-chlorobenzaldehyde (1 mmol)
and 6-amino-1,3-dimethyl uracil (1 mmol) was chosen as
model reaction (Scheme 1). It was evaluated without the
catalyst and also in the presence of different quantities of
The reaction was almost completed.
A plausible [14, 20 22] mechanism is proposed for the
[
Et N–SO H][Cl] at different temperatures under solvent-free preparation of pyrimido[4,5-b]quinolines using the acidic
3 3
conditions. The results are summarized in Table 1. Low yield IL ([Et
of the product was obtained under catalyst-free conditions are obvious from the mechanism, and consist of
Table 1, entry 1). The most appropriate conditions were found (i) accelerating nucleophilic reactions in steps 1, 3, and 4
to be 15 mol% of the ionic-liquid catalyst at T = 120 °C (Table 1, through activation of the electrophiles by its acidic
entry 3). Increasing the reaction temperature to 125 °C did not hydrogen, (ii) accelerating the removal of H O in steps 2
N–SO H][Cl]) (Scheme 2). The tasks of the catalyst
3
3
(
2
improve the results (Table 1, entry 7). Increasing the catalyst and 5 via conversion of OH to a good leaving group by the
quantity to 20 mol% slightly reduced the reaction time (Ta- acidic hydrogen, and (iii) accelerating the tautomerization
ble 1, entry 4). Nonetheless 15 mol% was chosen as less of dimedone to the enol form.
quantity of the catalyst is more economic and more compliant
with green chemistry principles.
To further confirm the merit of our protocol, the reac-
tion conditions and results with [Et N–SO H][Cl] for the
3
3
The scope and effectiveness of the present protocol synthesis of compounds 1, 6, and 10 were compared with
were studied through the synthesis of different derivatives those of other reported methods (Table 3). Our protocol is
of pyrimido[4,5-b]quinolines. For this purpose, dimedone superior than the protocols in entries 2–9 of Table 3 in
was reacted with miscellaneous arylaldehydes and terms of two or more of these factors: reaction times, yields,
6
-amino-1,3-dimethyl uracil using 15 mol% of [Et N–SO H] conditions (solvent-free vs. usage of organic solvent), and
3 3
[
Cl] at 120 °C in the absence of solvent. The results are temperature. The reaction times of our recently published
presented in Table 2. As it can be seen, benzaldehyde method summarized in entry 10 are less than those of our
and arylaldehydes bearing electron-attracting, electron- new protocol, while the reaction temperature, the yields,
donating and halogen substituents on ortho-, meta-, or and conditions of the two protocols are similar. Neverthe-
para-positions afforded the relevant products in high less, the procedure for the preparation of the catalyst in our
yields and short times. These results confirmed the gener- new protocol is easier and the amount of catalyst used in
ality and high efficacy of the protocol for the synthesis of the present protocol is less than in our previous one (0.033
pyrimido[4,5-b]quinolines.
vs. 0.080 g) while the workup procedure is also easier.
Cl
O
CHO
O
N
O
O
N
CH3
O
CH3
O
N
[Et N-SO H][Cl]
N
3
3
+
+
H C
Solvent-free
Different conditions
H C
3
3
O
H N
N
2
H C
H C
H
3
3
Cl
CH3
CH3
Scheme 1: The model reaction.

A. Zare and M. Dianat: Highly efficient synthesis of pyrimido[4,5-b]quinolines
87
Table : The synthesis of pyrimido[,-b]quinolines using [Et

N–SO H][Cl].

O
O
O
Ar
O
[
Et
3
N-SO
(15 mol%)
Solvent-free,120°C
3
H][Cl]
O
CH
3
CH
3
N
N
+
+
H
3
C
H
3
C
Ar
H
O
2
H N
N
O
N
H
N
O
H
3
C
H
3
C
CH
3
CH
3
a
Product No.
Ar
Time (min)
Yield (%)
M.p. (°C) found (reported) [ref.]
b









C
-O
-O
,-(CH
,-(CH
-CH
-HOC
-CH
,-Cl

H













– (–) []
– (–) []
– (–) []
– (–) []
– (–) []
– (–) []
– (–) []
– (–) []
> (>) []

NC
NC

H
H









O)
O)

C
C

H
H





b


OC H



H


b

C

H


b

C
H
H

H


b



-ClC
-ClC



– (–) []
> (>) []
b




a
b
Isolated yields. The reaction was almost completed.
4
.2 General procedure for the synthesis of
3
Conclusion
pyrimido[4,5-b]quinolines
In summary, we have developed a new method for the
synthesis of pyrimido[4,5-b]quinolines having several A mixture of compounds including dimedone (1 mmol,
advantages such as the use of an IL as catalyst, simple 0.140 g), aldehyde (1 mmol), 6-amino-1,3-dimethyl uracil
reaction procedure under solvent-free conditions, easy (1 mmol, 0.155 g), and [Et N–SO H][Cl] (0.15 mmol, 0.033)
3 3
purification of the products by recrystallization, superiority was well mixed at room temperature, and then vigorously
relative to many of the previously reported methods, and stirred at T = 120 °C by a small rod. After consuming the
good agreement with green chemistry principles.
starting materials (as observed by TLC), the reaction
mixture was cooled to room temperature, and the obtained
precipitate was recrystallized from EtOH-H O (95:5) to
2
afford the pure pyrimido[4,5-b]quinoline.
4
Experimental section
4.1 Materials and instruments
4
.3 Selected spectral data of the
Chemicals used were purchased from Fluka or Merck
synthesized pyrimido[4,5-b]quinolines
Chemical Companies. N,N-Diethyl-N-sulfoethanaminium
chloride ([Et N–SO H][Cl]) was synthesized according to 4.3.1 Product 3
3
3
our published method [34]. For identifying the products,
their melting points/spectral data were compared with M.p. 285–287 °C (lit. 281–285 °C [15]). — H NMR (300 MHz,
those reported in the literature. Thin-layer chromatog- DMSO-d –C), 1.05 (s, 3H,
–C), 1.97 (d, J = 16.0 Hz, 1H, CH–C=C), 2.21 (d, J = 16.1 Hz,
–C=O), 3.05 (s,
–N), 5.77 (s, 1H, CH–Ar), 7.31 (t,
25 MHz) were obtained on Bruker Avance DPX, FT-NMR J = 7.6 Hz, 1H, Ar), 7.45 (dd, J = 8.4, 1.4 Hz, 1H, Ar), 7.54 (t,
spectrometers. Melting points were measured using a J = 7.1 Hz, 1H, Ar), 7.76 (d, J = 8.1 Hz, 1H, Ar), 8.99 (s, 1H,
1
, 25 °C, TMS): δ = 0.87 (s, 3H, CH
6
3
raphy (TLC) using silica gel SIL G/UV 254 plates was uti- CH
3
1
lized for observing the respective reaction progress. H 1H, CH–C=C), 2.52–2.59 (AB system, 2H, CH
NMR (300, 400 or 500 MHz) and C NMR (75, 100, or 3H, CH –N), 3.47 (s, 3H, CH
3 3
2
1
3
1
1
3
Thermo Scientific 9200 instrument in open capillary NH). — C NMR (75 MHz, DMSO-d
tubes.
, 25 °C, TMS): δ = 26.9,
6
28.0, 29.4, 30.5, 30.8, 32.2, 32.5, 50.4, 90.2, 111.6, 124.1,

88
A. Zare and M. Dianat: Highly efficient synthesis of pyrimido[4,5-b]quinolines
H
O
O
[
Et N-SO H][Cl]
3
3
O
OH
O
CH3
CH3
CH3
CH3
O
Ar
O
O
O
[
Et N-SO H][Cl]
3
3
Ar
H
Ar
H
Step1
H
3
C
H
O
S
H C
3
Cl Et N
O
3
O
H
O
S
H
O
H
O
O
O
NEt Cl
O
3
O
[
Et N-SO H][Cl]
Ar
Ar
[Et N-SO H][Cl]
3 3
3
3
_
H C
H O
2
H C
3
3
O
Step2
H C
H C
3
3
CH3
N
H N
O
2
O
O
Ar
O
N
CH3
CH3
N
H C
Ar
3
[Et N-SO H][Cl]
3 3
O
O
H C
3
Step3
O
S
H C
3
H
N
O
H C
3
O
H N
2
O
O
NEt Cl
CH3
3
O
O
Ar
O
Ar
O
CH3
O
N
CH3
O
H C
N
[Et N-SO H][Cl]
3 3
3
Step 4
H C
3
H C
3
N
N
N
O
H N
2
H C
O
H
3
CH3
H
CH3
O
S
H
O
NEt Cl
3
O
O
Ar
O
O
Ar
O
N
CH3
CH3
N
N
Tautomerization
_
H C
H O
H C
3
3
2
Step6
N
H
N
O
N
O
Step 5
H C
O
H C
H
3
3
H
O
CH3
CH3
O
S
H
O
NEt Cl
3
O
Ar
O
CH3
N
H C
3
N
H
N
O
H C
3
CH3
Pyrimido[4,5-b]quinoline
Scheme 2: The proposed mechanism.

A. Zare and M. Dianat: Highly efficient synthesis of pyrimido[4,5-b]quinolines
89
Table : Comparison of the reaction conditions and the results of our protocol with those of other reported ones with the syntheses of
compounds , , and  as examples.
Entry
Catalyst
[Et N–SO
SBA-/PrN(CH
[H -DABCO][ClO
Nano-Fe @SiO
Conditions
Time (min) of product //
//
Yield (%) of product //
//
Ref.











H][Cl]
Solvent-free,  °C
Solvent-free,  °C
–
[]
[]
[]
[]
[]
[]
[]
[]
[]
a
a

PO

H

)

/– /
//
//
/– /


]

H
H
H

O,  °C

O,  °C

O,  °C
//
//
//
//

O


-SO H

p-Toluenesulfonic acid
//
//
b
[TSSECM]
Solvent-free,  °C
c
a
a
Catalyst-free
[bmim]Br ,  °C
– //
– //
a
a
[H
InCl
Nano-[FSRN][H

-DABCO][HSO

]

H
H

O/EtOH,  °C
O, reflux
/– /
/– /
a
a


– //
– //
d


PO

]
Solvent-free,  °C
//
//
a
b
In the work, this product has not been synthesized. N,N,N′,N′-Tetramethyl-N-(silica-n-propyl)-N′-sulfonic acid-ethylenediaminium chloride/
c
d
mesylate. -n-Butyl--methylimidazolium bromide. Nano-[Fe
  
O @-SiO @R-NHMe

][H

PO ].

1
1
27.3, 131.1, 133.2, 141.6, 144.7, 148.8, 150.5, 150.9, 161.0, CH –N), 3.47 (s, 3H, CH –N), 5.17 (s, 1H, CH–Ar), 7.09
3 3
94.9.
(t, J = 7.7, 2.1 Hz, 1H, Ar), 7.17–7.23 (m, 2H, Ar), 7.35
d, J = 7.6 Hz, 1H, Ar), 9.03 (s, 1H, NH).
(
4.3.2 Product 6
Acknowledgment: The authors acknowledge Research
Council of Payame Noor University for the support of this
work.
Author contributions: All the authors have accepted
responsibility for the entire content of this submitted
manuscript and approved submission.
Research funding: This work was supported by Research
Council of Payame Noor University.
Conflict of interest statement: The authors declare no
conflicts of interest regarding this article.
1
M.p. 305–307 °C (lit. 304–306 °C [22]). — H NMR (500 MHz,
DMSO-d , 25 °C, TMS): δ = 0.89 (s, 3H, CH –C), 1.03 (s, 3H,
6
3
CH –C), 2.04 (d, J = 16.1 Hz, 1H, CH–C=C), 2.20 (d,
J = 16.0 Hz, 1H, CH–C=C), 2.52 (d, J = 17.9 Hz, 1H, CH–C=O),
.60 (d, J = 17.4 Hz, 1H, CH–C=O), 3.09 (s, 3H, CH –N), 3.44
s, 3H, CH –N), 3.66 (s, 3H, CH –O), 4.82 (s, 1H, CH–Ar), 6.73
3 3
d, J = 7.1 Hz, 2H, Ar), 7.12 (d, J = 7.1 Hz, 2H, Ar), 8.96 (s, 1H,
NH). — C NMR (125 MHz, DMSO-d , 25 °C, TMS): δ = 27.1,
8.2, 29.7, 30.7, 32.7, 33.5, 40.4, 50.7, 55.5, 91.0, 112.5, 113.7,
3
2
3
(
(
13
6
2
1
29.2, 139.3, 144.2, 149.8, 151.2, 158.0, 161.3, 195.1.
4.3.3 Product 9
References
1
M.p. >300 °C (lit. >300 °C [19]). — H NMR (500 MHz, DMSO-
d , 25 °C, TMS): δ = 0.90 (s, 3H, CH –C), 1.05 (s, 3H, CH –C),
1
. Nargund L. V. G., Badiger V. V., Yarnal S. M. J. Pharm. Sci. 1992,
1, 365.
6
3
3
8
1
.99 (d, J = 16.1 Hz, 1H, CH–C=C), 2.21 (d, J = 16.5 Hz, 1H, CH–
C=C), 2.47 (d, J = 17.9 Hz, 1H, CH–C=O), 2.60 (d, J = 18.2 Hz,
H, CH–C=O), 3.06 (s, 3H, CH –N), 3.46 (s, 3H, CH –N), 5.15
s, 1H, CH-Ar), 7.26 (dd, J = 8.4, 2.0 Hz, 1H, Ar), 7.33–7.37 (m,
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