Tetrahedron Letters 60 (2019) 151025

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

Water-acetic acid mediated an efficient one-pot eco-friendly synthesis

of novel bis-isoxazolopyrroloquinoline derivatives
Sri Venkateswarlu Rayudu a,c,⇑, Dipankar Karmakar b, Pramod Kumar c
a
Department of Research and Development, Seutic Pharma Private Limited, IDA, Jeedimetla, Hyderabad 500055, Telangana, India
b
Director-Chemistry Services, Novick Biosciences, Private Limited, Balanagar, Hyderabad 500037, Telangana, India
c
Centre for Chemical Sciences, Institute of Science and Technology, Jawaharlal Nehru Technological University, Kukatpally, Hyderabad 500085, Telangana, India

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

Article history: An efficient, cost-effective and environmentally benign synthesis of novel tetracyclic bis-isoxazolopy-
Received 15 June 2019 rroloquinoline derivatives has been developed via one-pot four-component reaction of 4-amino-3-
Revised 4 August 2019 methyl-5-styrylisoxazoles, dimedone, aryl glyoxal monohydrates and 5-amino-3-methylisoxazole by
Accepted 7 August 2019
employing water as a reaction medium and acetic acid (AcOH) as a green promoter. The advantages of
Available online 9 August 2019
this protocol are environmentally friendly, metal-free, less reaction time, operational simplicity, high
yields, broad substrate scope and easy purification. Most significant of all, this method is green.
Keywords:
Ó 2019 Elsevier Ltd. All rights reserved.
Bis-isoxazolopyrroloquinoline
One-pot synthesis
Aqueous medium
Green chemistry

An important aspect of green chemistry describes the elimina-
tion of flammable, volatile, and toxic organic solvents, or their
replacement by low-cost ‘‘green solvents”. Water is becoming a
solvent of choice in organic synthesis because it is an eco-friendly,
low-cost, non-toxicity, easy availability, and inflammable reaction
medium which has generally had an remarkable effect on the rate
and selectivity of organic reactions over hydrophobic interactions
and enrichment of organic substances in the local hydrophobic
environment [1,2]. The development of non-hazardous, a simple,
efficient and environmentally-friendly synthetic methodologies
for the synthesis of highly functionalized compound libraries of
medicinal motifs is an attractive area of research in both pharma-
ceutical industry and academia [3]. Multi-component reactions
(MCRs) in water have been demonstrated to be powerful tools in
the field of organic synthesis, these reactions are identified by their
convergence, ease of execution, excellent yields, efficiency, reduc-
ing waste, and atom economy. In view of the increasing interest
in the synthesis of complex heterocyclic compound libraries, the
development of novel and synthetically valuable MCRs remains a
challenge for both academic and industrial research [4,5].
Nitrogen-containing heterocyclic scaffolds play an important
role in numerous natural products, and are extremely important
to synthetic and medicinal chemists because of their wide range
of biological activities [6]. Pyrroloquinolines are nitrogen-contain-
⇑ Corresponding author.
E-mail address: rayudujntuchem@gmail.com (S.V. Rayudu).
ing heterocyclic compounds having fused structures of pyrrole and
quinoline. Pyrroloquinoline core (Fig. 1) represents an important
family of alkaloids isolated from marine source, that exhibit a wide
range of biological activities [7–9]. These derivatives also have
attracted much attention recently, due to the other remarkable
biological and pharmacological activities, such as, anti-inflamma-
tory, anticonvulsant, antihypertensive, antipyretic, anti-MDR,
anti-oxidative, anti-viral activity, and anticancer activities [10–
12]. Similarly, the biological activity of substituted isoxazoles has
made them a focus of medicinal chemistry over the years. Isoxa-
zoles are potent analgesic, anti-inflammatory, antimicrobial,
COX-2 inhibitory, antitubercular, and anticancer agents [13–15].
The fused pyrroloquinoline and isoxazole frameworks display var-
ious biological activities. Therefore, the combination of these hete-
rocyclic scaffolds into one molecule stimulates tremendous
interest for pharmacological studies and drug design. There are
some methods developed for the synthesis of pyrroloquinoline
annulated heterocyclic derivatives due to their wide applications
[16,17]. However, the development of efficient, cost effective, and
environmentally benign protocol using a green reaction medium
for the synthesis of fused pyrroloquinoline derivatives is still desir-
able and in demand.
In view of the above evidences and in extension of our ongoing
importance on the development of novel route for the synthesis
and biological activity of new isoxazole derivatives [18], we
describe herein, for the first time an efficient, simple, and environ-
mentally friendly one-pot four-component method for the

https://doi.org/10.1016/j.tetlet.2019.151025
0040-4039/Ó 2019 Elsevier Ltd. All rights reserved.
2 S.V. Rayudu et al. / Tetrahedron Letters 60 (2019) 151025

in the presence of various catalysts such as p-TSA, I2, L-proline,

Fig. 1. Representative examples of biologically important pyrroloquinolines.
synthesis of tetracyclic bis-isoxazolopyrroloquinoline derivatives
from 4-amino-3-methyl-5-styrylisoxazoles, dimedone, aryl glyoxal
monohydrates and 5-amino-3-methylisoxazole in AcOH/H2O. To
the best of our knowledge, there are no reports for the synthesis
of tetracyclic bis-isoxazolopyrroloquinoline derivatives using
AcOH/H2O as a reaction medium under metal-free conditions.
To check the feasibility of our idea, initially the reactions were
employed by using 4-amino-3-methyl-5-styrylisoxazole 7a
(1 mmol), dimedone 8 (1 mmol), phenyl glyoxal monohydrate 9a
(1 mmol), and 5-amino-3-methylisoxazole 10 (1 mmol), as a
model substrates and the results are outlined in Table 1. It is well-
known that the choice of a relevant reaction medium is of vital role
for fruitful synthesis.
For optimization of the reaction conditions, the model reaction
was carried out in the absence and presence of different catalysts
in various solvents as well as under solvent-free reaction condi-
tions. The outcomes were summarized in Table 1. Initially, the
reaction was employed without using any catalyst under solvent-
free conditions at 100 °C for 18 h and it obtained the desired pro-
duct 11a in 20% yield (Table 1, entry 1). Next we tested the reaction
InCl3 and FeCl3 (10 mol%) without using any solvent medium and
observed some increase in the yield of the product 11a (Table 1,
entries 2–6). After the above examination, we also investigated
the effect of various solvents such as EtOH, CH3CN, DMSO, DMF,
Toluene, PEG-400 and H2O without catalysts afforded the desired
product 11a in 15–60% yield (Table 1, entries 7–13). In order to
make the reaction more efficient, next we performed the model
reaction in AcOH solvent at 100 °C, and the desired product was
obtained in 68% yield within 3 h (Table 1, entry 14). Inspired from
these outcomes, the reaction was employed in the mixture of AcOH
and H2O (1:9) at 100 °C to afford the desired product 11a in 88%
yield within 1 h (Table 1, entry 15). Increasing (20 and 50 mol%)
or decreasing (5 mol%) the ratio of AcOH/H2O did not improve
the product yield (Table 1, entries 16–18). Inferior results were
observed when the reaction was performed at low temperatures.
When the reaction mixture was examined in AcOH:CH3CN and
AcOH:EtOH (10 mol%) at 100 °C for 4 h, the product 11a was fur-
nished in 50–55% yield (Table 1, entries 19, 20). From these opti-
mization outcomes, we observed that AcOH:H2O (1:9 at 100 °C)
is the most effective solvent media for this one-pot synthesis.
With the optimized reaction conditions in hand, the utility of
the method was tested for the construction of bis-isoxazolopy-
rroloquinoline 11 derivatives through all permutations and combi-
nations of the substrates (Table 2). The generality of the reaction
was investigated by employing various 4-amino-3-methyl-5-
styrylisoxazoles 7, with dimedone 8, different aryl glyoxal mono-
hydrates 9, and 5-amino-3-methylisoxazole 10, in the one-pot
reaction process which progressed effectively to produce the
required products 11a–aa, in good yields (Table 2, entries 1–27).
In particular, the reactants can be not only phenyl groups having
either electron-withdrawing substitutents (EWG), such as chloro,
bromo, fluoro and nitro groups, but also bearing electron-donating
substitutents (EDG), such as, methoxy and methyl substitutents in
the 4-amino-3-methyl-5-styrylisoxazoles 7, were well tolerated

Table 1
Optimization of the reaction conditions 11a.a

Entry Catalyst (mol%) Solvent (v/v mol%) Temp ( °C) Time (h) Yieldb (%)
1 ─ ─ 100 18 20
2 p-TSA (10) ─ 100 10 30
3 I2 (10) ─ 100 10 30
4 L-Proline (10) ─ 100 12 35
5 InCl3 (10) ─ 100 8 40
6 FeCl3 (10) ─ 100 6 45
7 ─ EtOH 70 6 50
8 ─ CH3CN 80 10 40
9 ─ DMSO 80 5 45
10 ─ DMF 80 6 45
11 ─ Toluene 80 8 50
12 ─ PEG-400 100 4 60
13 ─ H2O 100 24 15
14 ─ AcOH 100 3 68
15 ─ AcOH:H2O (10) 100 1 88
16 ─ AcOH:H2O (20) 100 1 88
17 ─ AcOH:H2O (50) 100 1 80
18 ─ AcOH:H2O (5) 100 1 78
19 ─ AcOH:CH3CN (10) Reflux 4 50
20 ─ AcOH:EtOH (10) Reflux 4 55
a
All the reactions were performed with 7a (1 mmol), 8 (1 mmol), 9a (1 mmol) and 10 (1 mmol) in 5 mL of indicated solvents at reflux.
b
Isolated yields
 S.V. Rayudu et al. / Tetrahedron Letters 60 (2019) 151025 3

Table 2
Synthesis of different substituted bis-isoxazolo-pyrroloquinoline derivatives (11a-11aa).a

Entry Ar Ar0 Time (h) Yieldb (%) Product

1 C6H5 C6H5 1 88 11a
2 4-CH3C6H4 C6H5 1.6 82 11b
3 2-CH3C6H4 C6H5 2.0 78 11c
4 4-OCH3C6H4 C6H5 1.5 85 11d
5 2-OCH3C6H4 C6H5 1.8 80 11e
6 4-ClC6H4 C6H5 1.0 92 11f
7 2-ClC6H4 C6H5 1.2 80 11g
8 2,4-Cl2C6H3 C6H5 1.5 82 11h
9 4-BrC6H4 C6H5 1.0 90 11i
10 2-BrC6H4 C6H5 1.3 79 11j
11 4-FC6H4 C6H5 1.2 90 11k
12 4-NO2C6H4 C6H5 1.0 92 11l
13 C6H5 4-ClC6H4 1.2 88 11m
14 C6H5 2-ClC6H4 1.5 80 11n
15 C6H5 4-BrC6H4 1.0 90 11o
16 C6H5 2-BrC6H4 1.4 82 11p
17 C6H5 4-NO2C6H4 1.1 89 11q
18 C6H5 4-CH3C6H4 1.5 80 11r
19 C6H5 2-CH3C6H4 1.7 78 11s
20 C6H5 4-OCH3C6H4 1.4 82 11t
21 4-ClC6H4 2-BrC6H4 2.0 77 11u
22 4-OCH3C6H4 4-BrC6H4 1.3 82 11v
23 4-OCH3C6H4 3-BrC6H4 1.5 80 11w
24 C6H5 CH3 2.0 65 11x
25 2-thienyl C6H5 1.5 82 11y
26 2-furyl C6H5 1.2 80 11z
27 3-pyridyl C6H5 1.6 79 11aa
a
The reactions were performed with 7 (1 mmol), 8 (1 mmol), 9 (1 mmol) and 10 (1 mmol) in the presence of mixed AcOH/H2O (10 mol%) at 100 °C.
b
Isolated yields.

under the reaction conditions, outstanding to the final products in
moderate to good yields (Table 2, entries 2–23). Aminostyrylisox-
azoles 7 having with electron-withdrawing groups showed better
reactivity and resulted in higher yields compared to the electron-
donating groups. Higher yields could be observed by p-substituted
aminostyrylisoxazoles. Whereas o-substituted substrates, irrespec-
tive of EDG or EWG, provided the corresponding bis-isoxazolo-
pyrroloquinolines 11 in relatively a little bit lower yields. Next,
the substrate scope of various arylglyoxal monohydrates along
with 4-amino-3-methyl-5-styrylisoxazoles was also investigated.
The results are summarized in Table 2. As can be seen, the reaction
with different aryl glyoxal monohydrates bearing EDG or EWG
groups on phenyl ring progressed smoothly to obtain the required
products in moderate to good yields. Meanwhile, we also observed
that the aryl glyoxal monohydrates bearing electron-withdrawing
groups gave better yields than those having electron-donating
groups (Table 2, entries 13–23). Furthermore, the arylglyoxal
monohydrates with substitutents at the para- or meta-position
exhibited higher yields than those counterparts at the ortho-posi-
tion (Table 2, entries 21 vs 22, 23). Moreover, when a hetero aro-
matic nucleus like thiophene, furan, and pyridine was introduced
in aminostyrylisoxazole 7 as Ar, the reaction progressed well and
furnished the desired product in 79–82% yields (Table 2, entries
25–27). Unfortunately, when the methyl glyoxal was used in the
reaction process, the required product was observed with low
yields (Table 2, entry 24).
To examined the further structural diversity in this one-pot
reaction, we imported a series of isoxazoles 12a-d [18,19],
instead of 4-amino-3-methyl-5-styrylisoxazoles 7, it was
interesting that the required bis-isoxazolopyrroloquinoline
derivatives 13a-d were attained in good yields (65–78%) by using
this green synthetic method (Table 3). Remarkably, water is the
sole by-product in the reaction process, which makes the
reaction work-up very convenient. In all the cases, the desired
products were purified by simple filtration of the precipitate
formed and recrystallization from a methanol avoiding the
conventional chromatographic separation. The structures of the
newly synthesized compounds 11a-aa, 13a-d and 15 were
characterized by IR, 1H NMR, 13C NMR, and HRMS analysis.
To broaden the further structural diversity in the current reac-
tion, we introduced a different 1,3-dicarbonyl compound chro-
mene-2,4-dione 14 [18d], instead of the dimedone 8, it was
interesting that the desired product 15 was obtained in good
yield 80% by employing this green synthetic protocol (Scheme 1).
To understand the some insight mechanistic hypothesis for this
one-pot transformation, a preformed intermediate 16f [18k],
derived from compound 7f and dimedone 8, was reacted with 9a
and 10 under the standard reaction conditions. The
corresponding product 11f was obtained in 62% yield (Scheme 2).
These observations suggested that dimedone may be, prior to
reacting with 4-amino-3-methyl-5-styrylisoxazole, producing
intermediate 16f, which were further converted into the
corresponding product 11f.
On the basis of the experimental results, a plausible mechanism
for the formation of bis-isoxazolopyrroloquinolines 11 is proposed
in Scheme 3. Our main focus is to construct the isoxazole fused
quinoline frame work and wide substrate scope on isoxazole
derivatives for biological activity purpose. That’s why Initially,
4 S.V. Rayudu et al. / Tetrahedron Letters 60 (2019) 151025
Table 3
Substrate scope of bis-isoxazolopyrroloquinolines (13a-d).
Scheme 1. Substrate scope (15).
we carried out the condensation between compound 7 and dime-
done 8 in the presence of AcOH to give enamine intermediate 16,
which undergoes Knoevengel condensation followed by Michael
addition with compound 9 and 10 in the presence of AcOH to form
intermediate 17. The intermediate 17 then undergoes through an
intramolecular double cyclization process to afford the desired
product 11.
In conclusion, we have reported an efficient and environmentally
friendly method for the synthesis of novel tetracyclic bis-isoxa-
zolopyrroloquinolines derivatives from a one-pot, four-component
reaction of 4-amino-3-methyl-5-styrylisoxazoles, dimedone, aryl
glyoxal monohydrates and 5-amino-3-methylisoxazole in AcOH/
H2O under metal-free conditions. The advantages of this method
are operational simplicity, metal-free, excellent yields, chromatog-
raphy-free purification, the avoidance of toxic catalysts or solvents,
and wide substrate scope. Further investigations to evaluate the
applicability of this process to a broad range of substrates, synthesiz-
ing more complex products and testing their biological activity is an
ongoing goal of research in our laboratory.
General procedure for the synthesis of bis-isoxazolopyrroloquinoli-
nes (11): To 4-amino-3-methyl-5-styrylisoxazoles 7 [18h,20]
(1.0 mmol, 0.750 g) in 0.5 mL of AcOH and 4.5 mL of water,
dimedone 8 (1.0 mmol, 0.525 g) was added and the reaction
mixture refluxed at 100 °C for 10 min, followed by the addition
of aryl glyoxal monohydrates 9 (1.0 mmol, 0.569 g) and 5-amino-
3-methylisoxazole 10 (1 mmol, 0.367 g) and the reaction
continued for another 50 min. After completion of the reaction
(monitored by TLC), the mixture was cooled to room
temperature and poured into ice-cold water. The precipitate that
formed was filtered off, washed with ice cold water and the
crude product was purified by recrystallization from methanol to
give pure bis-isoxazolopyrroloquinolines 11.
(E)-4,4,9-Trimethyl-2-(3-methyl-5-styrylisoxazol-4-yl)-1-phe-
nyl-2,3,4,5-tetrahydroisoxazolo[5,4-b]pyrrolo[4,3,2-de]quinoline
(11a): Yield: 88%; mp 220–222 °C; IR (KBr): 3084, 2945, 2847,
1634, 1590, 1060, 733 cm1; 1H NMR (300 MHz, CDCl3): d 7.78–
7.16 (m, 10H), 6.70 (d, J = 12 Hz, 1H), 6.61 (d, J = 12 Hz, 1H), 2.81
(s, 2H), 2.41 (s, 2H), 2.25 (s, 3H), 2.10 (s, 3H), 1.10 (s, 6H); 13C
NMR (75 MHz, CDCl3): d 165.4, 162.3, 157.5, 154.7, 152.3, 137.5,
134.7, 132.3, 131.0, 129.8, 128.9, 128.6, 128.3, 127.7, 127.4,
124.7, 122.9, 113.4, 104.3, 100.2, 98.3, 52.3, 36.8, 34.7, 28.2, 12.8,
Scheme 2. Control experiment.
Scheme 3. A plausible mechanism for the synthesis of bis-isoxazolopyrroloquino-
lines 11.
11.1. HRMS (ESI-MS) calcd for C32H28N4NaO2 (M+Na)+ 523.2110,
found 523.2113.
Acknowledgments
S.V. Rayudu thanks the Department of chemistry JNTU-H and
Seutic Pharma Laboratories for providing research facilities. We
are grateful to Dr. M. N. Reddy and Dr. V. V. S. V. Prasad for their
valuable support and discussions.
Appendix A. Supplementary data
Supplementary data to this article can be found online at
https://doi.org/10.1016/j.tetlet.2019.151025.
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