ompg-C3N4/SO3H organocatalyst-mediated green synthesis of 1,2-dihydro-1-arylnaphtho[1,2-e][1,3] oxazin-3-ones under solvent-free and mild conditions: a fast and facile one-pot three-component approach

Article abstract of DOI:10.1007/s00706-020-02605-6

Abstract: In this research, we have described the synthesis of the well-ordered mesoporous graphite carbon nitride (ompg-C₃N₄) by applying SBA-15 as a potential hard silica template, and the catalytic performance of sulfonated well-o

Full text of DOI:10.1007/s00706-020-02605-6

Monatshefte für Chemie - Chemical Monthly
https://doi.org/10.1007/s00706-020-02605-6
ORIGINAL PAPER
ompg‑C3N4/SO3H organocatalyst‑mediated green synthesis
of 1,2‑dihydro‑1‑arylnaphtho[1,2‑e][1,3] oxazin‑3‑ones
under solvent‑free and mild conditions: a fast and facile one‑pot
three‑component approach
Nahal Goodarzi1 · Afsaneh Rashidizadeh1 · Hossein Ghafuri1
Received: 10 February 2020 / Accepted: 8 April 2020
© Springer-Verlag GmbH Austria, part of Springer Nature 2020
Abstract
In this research, we have described the synthesis of the well-ordered mesoporous graphite carbon nitride (ompg-C3N4) by
applying SBA-15 as a potential hard silica template, and the catalytic performance of sulfonated well-ordered mesoporous
graphite carbon nitride (ompg-C3N4/SO3H) as an environment‐friendly and efcient polymeric solid acid catalyst was inves-
tigated in the one‐pot preparation of 1,2-dihydro-1-arylnaphtho[1,2-e][1,3]oxazin-3-ones. This cyclocondensation reaction
was performed in the presence of various substituted aldehydes, urea, and 2-naphthol through mild and efcient solvent-free
method. The structure and morphology of ompg-C3N4/SO3H were characterized using various instrumental analysis methods
including FT-IR, EDS, FESEM, TEM, TGA, DTG, XRD, and BET. The simplicity of the process, low reaction times, simple
workup, high to quantitative yields, avoiding the utilization of organic solvents, and reusability of the as-prepared catalyst
are several prominent advantages of this present synthetic method.
Graphic abstract
Keywords Carbon nitride · Organocatalyst · Condensation reaction · Naphthoxazinone · Green synthesis
Introduction
Ordered mesoporous materials (OMMs) with tunable pore
sizes, high surface active sites, and uniform pore structures
indicate potential performances in the novel catalytic pro-
cesses. In particular, surface modifcation is an interest-
ing feature of these materials for improving their catalytic
performance [1, 2]. Accordingly, functionalized ordered
mesoporous materials with covalently bound sulfonic acid
have attracted a great amount of attention as an appropriate
solid acid catalyst [3, 4].
Electronic supplementary material The online version of this
article (https://doi.org/10.1007/s00706-020-02605-6) contains
supplementary material, which is available to authorized users.
* Hossein Ghafuri
ghafuri@iust.ac.ir
1
Catalysts and Organic Synthesis Research Laboratory,
Department of Chemistry, Iran University of Science
and Technology, 16846-13114 Tehran, Iran
Vol.:(0123456789)
1 3

N. Goodarzi et al.
Over the recent few years, porous carbon materials have
been widely used in the various categories of science includ-
ing supercapacitors, electrode materials, sorbents, gas stor-
ages, catalyzers, and fuel cells due to the excellent physical
and chemical features such as stability, low density, broad
availability, and electric and thermal conductivity [5]. Poly-
meric graphitic carbon nitride (g-C3N4) is the main class
of carbonaceous materials with electron-rich surface and
environment-friendly nature. Generally, g-C3N4 substruc-
ture, based on aromatic C–N heterocycles and optimized
van der Waals forces between its two-dimensional conju-
gated planes, can be prepared by polymerization of aford-
able nitrogen-containing materials like melamine, urea,
cyanamide, thiourea, and dicyandiamide [6]. Reasonable
physical and chemical property, unique electronic property,
exclusive thermal and chemical resistance, and high specifc
surface area [7] make this material be applied in many sci-
entifc felds such as fuel cell [8], sensor [9], solar cell [10],
metal-free catalyst [11], heterogeneous photocatalyst [12],
energy storage [13], oxygen reduction reaction (ORR) [14],
hydrogen evolution [15], photocatalytic degradation of pol-
lutants [16, 17], and oxidation [18]. The preparation of well-
ordered mesoporous g-C3N4 leads to higher specifc surface
area, stronger adsorption capacity, and larger pore volume
and increases active chemical sites, thereby enhancing the
performance of g-C3N4 as an efcient catalyst and catalyst
support [19, 20]. As a result of the tremendous properties of
the ordered mesoporous g-C3N4, a variety of researches have
been reported about the synthesis and catalytic application
of this material during the past few decades [21–24].
antipyretic, and anticonvulsant [29]. Moreover, naph-
thalene-condensed 1,3-oxazin-3-ones with antimicrobial
properties [30] are applied as the potential starting mate-
rials in the synthesis of phosphonic ligands for asym-
metric catalysis [31]. Previously, some naphthalene-con-
densed 1,3-oxazin-3-ones were prepared through reaction
between aminoalkylnaphthols with phosgene [32] or car-
bonyl diimidazole in the presence of triethylamine [33].
On the other hand, designing a safer synthetic method in
the presence of less harmful reagents for the synthesis of
naphthoxazinone derivatives has attracted a remarkable
amount of attention during recent years. In this context,
some syntheses of 1-aryl-1,2-dihydronaphtho[1,2-e]-
[1,3]oxazin-3-ones have been reported using various cata-
lysts such as [PyPS][HSO4] [34], TMSCl [35], Cu nano-
particles [36], Zn (OTF)2 [37], HClO4/SiO2 [38], [bmim]
Br [39], TMSCl/NaI [40], and ZnO NPs [41], via cyclocon-
densation reaction of β-naphthol with substituted aldehydes
and urea. However, the mentioned methods are associated
with various drawbacks such as wearisome reaction time,
use of hazardous organic solvent, high reaction temperature,
and lower yield of products. Therefore, the development of
a novel synthetic methodology for the synthesis of these
compounds under milder conditions is still in great demand.
Accordingly, in connection with our previous eforts toward
the synthesis of ompg-C3N4-based heterogeneous organo-
catalysts [42], we have recently reported the synthesis of
pharmaceutically interesting compounds catalyzed by super-
active sulfonated highly ordered mesoporous graphitic car-
bon nitride (ompg-C3N4/SO3H) as an efcient heterogeneous
solid acid catalyst [43, 44]. Herein, we report the applica-
tion of ompg-C3N4/SO3H as a more practical and efcient
catalyst for the facile and green synthesis of 1,2-dihydro-
1-arylnaphtho[1,2-e][1,3]oxazin-3-one derivatives. Owing
to the several superior properties of ompg-C3N4/SO3H such
as strong acidity strength, high activity, and environmen-
tally friendly nature, the mentioned reaction was conducted
under milder conditions and in the absence of solvent with
high to quantitative yields of products (Scheme 1).
Given the increasing importance of designing atom
economic strategies in synthetic organic chemistry, multi-
component reactions (MCRs) emerged as the convergent,
simple, time and energy efcient, and selective processes
[25]. In this regard, MCRs could be extremely useful in the
ideal synthesis of heterocyclic compounds. Considering the
important activities of N-containing heterocyclic compounds
in the biological and pharmaceutical felds, chemical indus-
tries, and also as the applicable intermediates in organic
syntheses, numerous methodologies have been focused on
the efcient synthesis of these materials [26].
Results and discussion
One of the important types of N-containing heterocy-
clic compounds is aromatic-condensed oxazinone with
various promising biological activities such as antimicro-
bial [27], anticancer [28], analgesic, anti-infammatory,
Sulfonated ordered mesoporous graphitic carbon nitride
(ompg-C3N4/SO3H) was prepared and characterized through
the method that we have recently reported (further details
Scheme 1
1 3

ompg‑C3N4/SO3H organocatalyst‑mediated green synthesis of…
and characterization information are available in the sup-
porting information) [43, 44]. Preservation of the original
framework of ompg-C3N4 after immobilization of the—
SO3H groups is indicated in Fig. S2, S3. Moreover, the
exact amounts of C (27.83%), H (2.91%), N (47.06%), and
S (2.72%) elements in the ompg-C3N4/SO3H composition
was identifed by elemental analysis. It should be noted that
a signifcant decrease in the BET surface area of ompg-C3N4
as compared with the silica template may be related to the
partial pore collapse of the mesostructure due to the poor
difusion of cyanamide in the pores of the mesoporous silica
template, also the high shrinkage as a result of the condensa-
tion at high temperature, and in the process of the elimina-
tion of the silica template (Fig. S6) [45–47]. According to
the TGA and DTA analyses of ompg-C3N4 and ompg-C3N4/
SO3H (Fig. S5), ompg-C3N4/SO3H possesses high thermal
stability due to the presence of van der Waals forces between
the sulfonic acid groups and mesoporous graphitic carbon
nitride support. FESEM image of ompg-C3N4/SO3H (Fig.
S4) and TEM image of ompg-C3N4/SO3H (Fig. 1) clearly
confrmed the rod-like mesoporous structure and uniform
framework of ompg-C3N4/SO3H.
led to completion of the reaction in 5 min with 87% yield
of the desired product (Table 1, entry 7). For evaluation of
the solvent efect, the model reaction was investigated by
applying various solvents (including EtOH, H2O, MeOH,
CH3CN, toluene) and in solvent-free conditions (Table 1,
entries 8–12).The results revealed that, in the presence of
both types of protic and aprotic solvents, only a trace amount
of product was obtained and the best result was achieved in
the absence of solvent. In continuance, the infuence of tem-
perature was investigated (Table 1, entries 13–17). Relying
on the obtained results, as the temperature was conducted
to 100 °C, the desired product was formed at a shorter reac-
tion time and the yield increased to 87% (Table 1, entry
17). Moreover, by increasing the temperature, no noticeable
change occurred in the time and yield of the reaction. To
acquire a suitable amount of catalyst, the model reaction
was examined by applying 5, 10, 15, 20, and 30 mg of ompg-
C3N4/SO3H at 100 °C (Table 1, entries 17–21). It was found
that 20 mg of ompg-C3N4/SO3H was sufcient to give the
desired product in 97% yield and very short reaction time
(Table 1, entry 20).
The catalytic activity of ompg-C3N4/SO3H and the role of
the –SO3H group were investigated using various forms of
g-C3N4 in the model reaction (Table 2). The results clearly
proved that functionalization of well-ordered mesoporous
graphitic carbon nitride with the –SO3H group led to a
signifcant improvement in the model reaction in terms of
time and yield. In particular, because of the incorporation
of nitrogen atoms in the carbon architecture, high amounts
of –SO3H groups were loaded on the ompg-C3N4, which led
to increase in the acidity strength of the catalyst. Also, it is
anticipated that the development of positive charge on the
nitrogenous framework after –SO3H immobilization leads
to the high acidity strength of ompg-C3N4/SO3H and thus
enhances its catalytic performance.
To evaluate the performance of ompg-C3N4/SO3H in the
preparation of 1,2-dihydro-1-arylnaphtho[1,2-e][1,3]oxa-
zin-3-ones, a one‐pot cyclocondensation multicomponent
reaction was investigated over a systematic study. For this
purpose, the three-component reaction between benzalde-
hyde (1) (1.0 mmol), urea (2) (1.2 mmol), and 2-naphthol
(3) (1.0 mmol) was considered as a model reaction. The
optimal conditions were determined through screening the
efect of various solvents at several temperatures and dif-
ferent amounts of the catalyst (Table 1). It seems remark-
able that the reaction could not aford the desired product
in the absence of the catalyst after 2 h (Table 1, entries
1–6). Signifcantly, using ompg-C3N4/SO3H as a catalyst
After determining the optimum conditions, the generality
of this method was investigated using various substituted
aromatic aldehydes in the presence of ompg-C3N4/SO3H at
100 °C under solvent-free conditions (Table 3, entries 1–11).
The results proved that all of the substituted aldehydes with
electron-withdrawing groups (Cl, F, NO2, CN) and electron-
donating groups (OH, Me, OMe,) at diverse positions of the
aromatic ring aforded the desired products in high yields
and reasonable times.
The reusability of ompg-C3N4/SO3H as a heterogeneous
organocatalyst in the model reaction was also investigated.
After completing, ompg-C3N4/SO3H was fltered of, rinsed,
and dried and then reused in the next reaction. According
to the obtained results, ompg-C3N4/SO3H could be reused
up to fve cycles with insignifcant loss of activity (Fig. 2).
Relying on our experimental results and using the
pathways previously described in the literature [34,
48, 52], a probable mechanism for the formation of
Fig. 1 TEM micrographs of ompg-C3N4/SO3H
1 3

N. Goodarzi et al.
Table 1 Determination of the optimal conditions
Entry
Solvent
Amount of catalyst/mg
Temp/°C
Time/min
Yield/%a
1
2
3
4
5
6
7
8
–
–
–
–
–
–
–
10
10
10
10
10
10
10
10
10
10
10
5
150
120
120
120
120
120
120
5
120
120
120
120
120
120
120
5
5
5
5
5
5
5
–
–
–
–
–
–
EtOH
H2O
MeOH
CH3CN
Toluene
–
EtOH
H2O
MeOH
CH3CN
Toluene
–
Refux
Refux
Refux
Refux
Refux
150
Refux
Refux
Refux
Refux
Refux
–
–
160
120
100
100
100
100
100
87
Trace
Trace
32
25
–
9
10
11
12
13
14
15
16
17
18
19
20
21
–
–
MeOH
–
–
–
–
–
–
–
87
87
87
81
93
97
97
15
20
30
Reaction conditions: benzaldehyde (1, 1.0 mmol), urea (2, 1.2 mmol), 2-naphthol (3, 1.0 mmol), 3.0 cm3 solvent, and catalyst: ompg-C3N4/SO3H
aIsolated yield
Table 2 A comparison of the
catalytic performance of ompg-
C3N4/SO3H with other forms of
g-C3N4
Entry
Catalyst
Amount of cata- Solvent
lyst/mg
Time/min
Yield/%a
1
2
3
4
5
6
ompg-C3N4
Bulk g-C3N4
Nanosheet g-C3N4
ompg-C3N4/SO3H
Bulk ompg-C3N4/SO3H
Nanosheet g-C3N4/SO3H
20
20
20
20
20
20
–
–
–
–
–
–
80
80
80
5
5
5
–
–
Trace
97
51
69
Reaction conditions: benzaldehyde (1, 1.0 mmol), urea (2, 1.2 mmol), 2-naphthol (3, 1.0 mmol)
aIsolated yield
1,2-dihydro-1-arylnaphtho[1,2-e][1,3]oxazin-3-ones
has been proposed in Scheme 2. The reaction is started
by the activation of the carbonyl functional group of
benzaldehyde (2) through protonation with ompg-C3N4/
SO3H as a Bronsted acid that increases the electrophilic
nature, followed bythe nucleophilic attack of urea (2)
1 3

ompg‑C3N4/SO3H organocatalyst‑mediated green synthesis of…
Table 3 ompg-C3N4/SO3H catalyzed reaction for the synthesis of
1,2-dihydro-1-arylnaphtho[1,2-e][1,3]oxazin-3-ones in the presence
of various aldehydes
Entry
R
Product
Time/min
Yield/%a
M.p. /°C
Lit. m.p./°C
1
2
3
4
5
6
7
8
H
4-Cl
4-Me
4-OH
4-OMe
3-NO2
4-F
4a
4b
4c
4d
4e
4f
4g
4h
4i
5
5
5
8
5
10
13
5
5
8
97
95
91
89
93
75
78
89
81
87
96
220–222
210–213
164–165
180–183
188–190
210–212
199–201
247–250
171–174
189–191
189–190
210–222 [48]
212–214 [38]
164–166 [41]
181–183 [49]
188–190 [41]
210–212 [48]
198–200 [41]
248–250 [50]
172–174 [51]
189 [40]
2-Cl
9
10
11
4-NO2
3-OH
4-CN
4j
4k
5
This work
Reaction conditions: aldehyde 1 (1.0 mmol), urea (2, 1.2 mmol), 2-naphthol (3, 1.0 mmol), 100 °C, catalyst: ompg-C3N4/SO3H (20 mg)
aIsolated yield
active –SO3H. Subsequently, conversion of IV into its acti-
vated enolate form V (through tautomerization) and proton
transfer aford intermediate VI. Eventually, intramolecular
cyclization forms the desired products 4 with removal of
ammonia.
A comparison of the catalytic capability of ompg-C3N4/
SO3H with some other reported catalysts in the literature
clearly shows an excellent catalytic performance of as-
synthesized catalyst to other catalysts in the preparation
of 1,2-dihydro-1-arylnaphtho[1,2-e][1,3]oxazin-3-one
derivatives under mild reaction conditions in low reaction
time with high yield (Table 4).
Fig. 2 Recycling of the ompg-C3N4/SO3H in the model reaction
Conclusion
In conclusion, we have presented a highly efective and
forming intermediate I. Thereafter, proton transfer leads
to intermediate II, which upon dehydration generates reac-
tive acylium intermediate III. The subsequent reaction of
β-naphthol (3) with the resulting acylium forms intermedi-
ate IV. Simultaneously, a proton transfer from β-naphthol
(3) to the sulfanic group missing from intermediate III to
intermediate IV leads to the resumption of catalytically
green synthetic protocol for the preparation of pharmaco-
logical interesting 1,2-dihydro-1-arylnaphtho[1,2-e][1,3]-
oxazin-3-one derivatives applying ompg-C3N4/SO3H as
an efective superactive heterogeneous solid acid organo-
catalyst under mild reaction conditions. This novel pro-
cedure is associated with notable benefts, such as being
environmentally safe and having short process time,
1 3

N. Goodarzi et al.
Scheme 2
Table 4 Comparison between
ompg-C3N4/SO3H performance
with some previously reported
performancesa
Entry
Catalyst (amount of catalyst)
Solvent
Temp./°C
Time/min
Yieldb/%
1
2
3
4
5
[SiO2–VO(OH)2] (2 mg)
Graphene oxide (35 w%)
Silica-bonded S-sulfonic acid (20 mg)
FeCl3/SiO2NPs
–
–
–
–
–
130
120
150
150
100
60
25
60
10
5
82 [49]
87 [53]
90 [48]
85 [54]
ompg-C3N4/SO3H (20 mg)
97
This work
aReaction conditions: benzaldehyde (1, 1.0 mmol), urea (2, 1.2 mmol), 2-naphthol (3, 1.0 mmol)
bIsolated yield
1 3

ompg‑C3N4/SO3H organocatalyst‑mediated green synthesis of…
facile workup, high yield, and noticeable reusability of
the catalyst.
FT-IR (KBr): v=3280, 2925, 2227, 1745, 1631, 1508, 1444,
1220, 811 cm−1; 1H NMR (500 MHz, DMSO-d6): δ=8.99
(d,1H, –NH, J=5.15 Hz), 8.01 (d, 1H, Ar–H, J=8.95 Hz),
7.96 (d, 1H, Ar–H, J=1.5 Hz), 7.39–7.83 (m, 1H, Ar–H),
6.35 (d, 1H, CH, J= 3.15 Hz) ppm; 13C NMR (125 MHz,
DMSO-d6): δ=53.2, 78.03, 110.87, 113.00, 116.90, 118.42,
122.93, 125.22, 127.56, 128.02, 128.71, 130.41, 130.64,
133.02, 147.59, 147.76, 149.03 ppm.
Experimental
All of the chemicals and solvents were commercially avail-
able and purchased from Merck and Fluka. All reactions
and the purity of the products were monitored by analyti-
cal TLC on Al plates coated with 0.2 mm silica gel F254.
An Electrothermal 9100 apparatus was applied to check out
melting points. FT-IR spectral information was obtained by a
Shimadzu spectrometer using KBr pill in the 400–4000 cm−1
region. The specifc surface areas and pore diameter distri-
butions were recognized by the adsorption branch of the
BJH isotherm. The FESEM images were extracted on a
MRIA3 TESCAN-XMU, and TEM images were acquired by
Zeiss-EM10C-100 kV model. The X-ray difraction (XRD)
measurements were taken on a PANalytical X-PERT-PRO
MPD difractometer using Cu Kα (λ = 1.5406 Å) in the
range of 2θ = 5° to 80° with a step size of 0.02°. Elemen-
tal analysis was examined by applying a CHNS analyzer
(Thermo Flash EA 1112). Identifcation of products was
performed with an 1H and 13C NMR spectra using Bruker
DRX-500 Avance spectrometer in DMSO-d6. EDX spectra
were obtained using Numerix DXP-X10P. TGA and DTG
analyses of the as-prepared catalyst were carried out with
STA504 analyzer system at 20–800 °C.
References
1. Taguchi A, Schu F (2005) Microporous Mesoporous Mater 77:1
2. Ahmadi E, Ramazani A, Hamdi Z, Mohamadnia AMZ (2015)
Silicon 7:323
3. Mohammadi G, Lashgari N, Badiei A (2015) J Mol Catal A Chem
397:166
4. Wang Y, You J, Liu B (2019) React Kinet Mech Catal 128:493
5. Liang C, Li Z, Dai S (2008) Chem Int Edn 47:3696
6. Lakhi KS, Park DH, Al-Bahily K, Cha W, Viswanathan B, Choy
JH, Vinu A (2017) Chem Soc Rev 46:72
7. Dong G, Zhang Y, Pan Q, Qiu J (2014) Photochem Photobiol C
Photochem Rev 20:33
8. Di Noto V, Negro E (2010) Electrochim Acta 55:7564
9. Lee SP, Lee JG, Chowdhury S (2008) Sensors 8:2662
10. Xu J, Wang G, Fan J, Liu B, Cao S, Yu J (2015) J Power Sources
274:77
11. Schubert MM, Hackenberg S, Van Veen AC, Muhler M, Plzak V,
Behm RJ (2001) J Catal 197:113
12. Wang Y, Wang X, Antonietti M (2012) Angew Chem Int Edn
51:68
13. Wang D, Li F, Liu M, Lu GQ, Cheng HM (2008) Angew Chem
Int Edn 120:379
14. Zhang Y, Huang N, Zhou F, He Q, Zhan S (2018) J Chin Chem
Soc 65:1431
General procedure for the synthesis of ompg‑C3N4/
SO3H
15. Wang X, Maeda K, Chen X, Takanabe K, Domen K, Hou Y, Fu
X, Antonietti M (2009) J Am Chem Soc 131:1680
16. Liu M, Wei S, Chen W, Gao L, Li X, Mao L, Dang H (2019) J
Chin Chem Soc 66:1044
Sulfonated ordered mesoporous graphitic carbon nitride
(ompg-C3N4/SO3H) was prepared through the method that
we have recently reported [43, 44].
17. Yin J, Wu Z, Fang M, Xu Y, Zhu W, Li C (2018) J Chin Chem Soc
65:1044
18. Chen X, Zhang J, Fu X, Antonietti M, Wang X (2009) J Am Chem
Soc 131:11658
19. Zhao H-M, Di C-M, Wang L, Chun Y, Xu Q-H (2015) Micropo-
rous Mesoporous Mater 208:98
General procedure for the synthesis of 4
20. Yang Z, Zhang Y, Schnepp Z (2015) J Mater Chem A 3:14081
21. Gao X, Jiao X, Zhang L, Zhu W, Xu X, Ma H, Chen T (2015) RSC
Adv 5:76963
To a mixture of aldehyde 1 (1.0 mmol), urea (2, 1.2 mmol)
and 2-naphthol (3, 1.0 mmol), ompg-C3N4/SO3H (20.0 mg)
was added. The reaction mixture was stirred at 100 °C in the
absence of solvent (Table 2). After the reaction was com-
plete, it was detected using TLC (hexane/EtOAc 2:1), the
temperature changed from 100 to 80 °C, and 5 cm3 ethanol
was poured to the reaction vessel and then stirred for 10 min.
The resulting reaction mixture was fltered to separate the
solid catalyst and the pure products 4 were obtained by cool-
ing the fltered solution and recrystallization with ethanol.
22. Gong Y, Zhang P, Xu X, Li Y, Li H, Wang Y (2013) J Catal
297:272
23. Liu Y, Yu Y-X, Zhang W-D (2014) Int J Hydrogen Energy
39:9105
24. Bu Y, Chen Z, Li W (2014) Appl Catal B Environ 144:622
25. Do A, Wang W, Wang K (2012) Chem Rev 112:3083
26. Okamoto S, Iwakubo M, Kobayashi K, Sato F (1997) J Am Chem
Soc 119:6984
27. Sunil D, Upadhya SH, Murugappan R (2013) Res J Pharm Sci
2:15
28. Ouberai M, Asche C, Carrez D, Croisy A, Dumy P, Demeunynck
M (2006) Bioorg Med Chem Lett 16:4641
1‑(4‑Cyanophenyl)‑1,2‑dihydronaphtho[1,2‑e][1,3]oxa‑
zin‑3‑one (4k, C19H12N2O2) White solid; m.p.: 189–190 °C;
29. George M, Joseph L, Sadanandan HR (2016) Int J Pharm Pharm
Res 6:14
1 3

N. Goodarzi et al.
30. Latif N, Mishriky N, Assad FM (1982) Aust J Chem 35:1037
31. Wang Y, Li X, Ding K (2002) Tetrahedron Asymmetry 13:1291
32. Szatmári I, Hetényi A, Lázár L, Fülöp F (2004) J Heterocycl Chem
41:367
45. Liu J, Yan J, Ji H, Xu Y, Huang L, Li Y, Song Y, Zhang Q, Xu H
(2016) Mater Sci Semicond Process 46:59
46. Park SS, Chu S-W, Xue C, Zhao D, Ha C-S (2011) J Mater Chem
21:10801
33. Cimarelli C, Palmieri G, Volpini E (2004) Can J Chem 82:1314
34. Dong F, Li-Fang Y, Jin-Ming Y (2013) Res Chem Intermed
39:2505
47. Li X-H, Wang X, Antonietti M (2012) Chem Sci 3:2170
48. Nikna K, Abolpour P (2015) J Chem Sci 127:1315
49. Zolfgol MA, Safaiee M, Afsharnadery F, Bahraminejad N, Bagh-
ery S, Salehzadeh S, Maleki F (2015) RSC Adv 5:100546
50. Olyaei A, Sadeghpour M, Zarnegar M (2013) Chem Heterocycl
Compd 49:1374
35. Jiang C, Geng X, Zhang Z, Xu H, Wang C (2010) J Chem Res
34:19
36. Kumar A, Saxena A, Dewan M, De A, Mozumdar S (2011) Tet-
rahedron Lett 52:4835
51. Basavegowda N, Somai Magar KB, Mishra K, Lee YR (2014)
New J Chem 38:5415
37. Hajra A, Kundu D, Majee A (2009) J Heterocycl Chem 46:1019
38. Ahangar HA, Mahdavinia GH, Marjani K, Hafezian A (2010) J
Iran Chem Soc 7:770
52. Wu J, Du X, Ma J, Zhang Y, Shi Q, Luo L, Song B, Yang S, Hu
D (2014) Green Chem 16:3210
39. Dabiri M, Sadat Delbari A, Bazgir A (2007) Heterocycles 71:543
40. Sabitha G, Arundhathi K, Sudhakar K, Sastry BS, Yadav JS
(2010) J Heterocycl Chem 47:272
53. Gupta A, Kour D, Gupta VK, Kapoor KK (2016) Tetrahedron Lett
57:4869
54. Safaei-Ghomi J, Zahedi S, Ghasemzadeh MA (2012) Iran J Catal
2:27
41. Rao GBD, Kaushik MP, Halve AK (2012) Tetrahedron Lett
53:2741
42. Ghafuri H, Jafari G, Rashidizadeh A, Manteghi F (2019) Mol
Catal 475:110491
Publisher’s Note Springer Nature remains neutral with regard to
jurisdictional claims in published maps and institutional afliations.
43. Fard MAD, Ghafuri H, Rashidizadeh A (2019) Microporous
Mesoporous Mater 274:83
44. Ghafuri H, Goodarzi N, Rashidizadeh A, Fard MAD (2019) Res
Chem Intermed 45:1
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