Fulvic Acid: An Efficient and Green Catalyst for the One-pot Four-component Domino Synthesis of Benzo[a]phenazine Annulated Heterocycles in Aqueous Medium

Full text of DOI:10.1080/00304948.2019.1697608

Organic Preparations and Procedures International
The New Journal for Organic Synthesis
ISSN: 0030-4948 (Print) 1945-5453 (Online) Journal homepage: https://www.tandfonline.com/loi/uopp20
Fulvic Acid: An Efficient and Green Catalyst for
the One-pot Four-component Domino Synthesis
of Benzo[a]phenazine Annulated Heterocycles in
Aqueous Medium
Afshin Yazdani-Elah-Abadi, Maliheh Razeghi, Nasim Shams, Mehrnoush
Kangani & Razieh Mohebat
To cite this article: Afshin Yazdani-Elah-Abadi, Maliheh Razeghi, Nasim Shams, Mehrnoush
Kangani & Razieh Mohebat (2020) Fulvic Acid: An Efficient and Green Catalyst for the One-
pot Four-component Domino Synthesis of Benzo[a]phenazine Annulated Heterocycles in
Aqueous Medium, Organic Preparations and Procedures International, 52:1, 48-55, DOI:
10.1080/00304948.2019.1697608
To link to this article: https://doi.org/10.1080/00304948.2019.1697608
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ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
2020, VOL. 52, NO. 1, 48–55
https://doi.org/10.1080/00304948.2019.1697608
EXPERIMENTAL PAPER
Fulvic Acid: An Efficient and Green Catalyst for the One-pot
Four-component Domino Synthesis of Benzo[a]phenazine
Annulated Heterocycles in Aqueous Medium
Afshin Yazdani-Elah-Abadia, Maliheh Razeghib, Nasim Shamsc, Mehrnoush
Kanganid, and Razieh Mohebatc
b
aDepartment of Biology, Science and Art University, Yazd, Iran; Department of Food Science and
c
Technology, Shahid Beheshti University of Medical Science, Tehran, Iran; Young Researchers and Elite
d
Club, Islamic Azad University, Yazd Branch, Yazd, Iran; Department of Chemistry, Faculty of Science,
University of Sistan and Baluchestan, Zahedan, Iran
ARTICLE HISTORY Received 5 July 2019; Accepted 4 September 2019
Fulvic acid is a naturally occurring organic compound found in soil and plants. It is
recognized for its ability to balance and energize cell biological processes. Fulvic acid lit-
erally transforms minerals and other nutrients into minute molecules. Nutrient uptake
is thus more efficient because of fulvic acid. With better nutrient uptake, cell respiration
and energy production increase. Although fulvic acid has been well researched, it is just
now beginning to come into prominence (Figure 1).1
In recent years, interest in green chemistry2–4 has developed, and a major challenge
to organic chemists is to reduce the use of organic solvents and toxic reagents for facile,
efficient, and nonpolluting synthetic procedures. In this area, the use of natural materi-
als as promising catalysts in organic reactions has received considerable attention, due
to their green credentials.5–10 Aqueous phase organic synthesis is appealing to chemists
because it overcomes the harmful effects associated with organic solvents and is envir-
onmentally benign. Moreover, when using water as the medium, surfactants can be
used to build micelles and provide better chemical yields and shorter reaction times due
to hydrogen bonding, hydrophobic effects and high polarity.11–13
In order to make possible economic savings and pollution prevention, multi-compo-
nent domino reactions (MDRs), have considerable potential for the synthesis of complex
heterocyclic molecules and for drug design and drug discovery, arising from minimiza-
tion of time, waste, energy, and cost.14–17
Phenazine based compounds are nitrogen-containing heterocycles that are present in
natural products and synthetic materials showing a variety of biological functions,
including antibiotic, antimicrobial, antimalarial and antiparasitic activities.18–23 By virtue
of their DNA intercalating ability, they exhibit anticancer activity in leukemia and solid
tumors. For example, pyridophenazinediones and pyridazinophenazinedione derivatives
are known for their antitumor activities.24,25
CONTACT Afshin Yazdani-Elah-Abadi
afi_yazdani@yahoo.com
Department of Biology, Science and Art University,
Yazd, Iran
Color versions of one or more of the figures in the article can be found online at www.tandfonline.com/uopp.
ß 2020 Taylor & Francis Group, LLC

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
49
Figure 1. The structure of fulvic acid.
Some catalysts have been reported to facilitate the synthesis of benzo[a]phenazine
annulated heterocycles, such as: aqueous acetic acid,26 p-TSA-PEG 400,17 DABCO,27
glacial acetic acid,28 and H2SO4.29
We have been engaged in the development of methodologies for the synthesis of het-
erocycles using green reaction media.30–35 We here report an efficient and green synthe-
sis of benzo[a]pyrano[2,3-c]phenazine and benzo[a]chromeno[2,3-c]phenazine in the
presence of fulvic acid as catalyst in H2O at 60 ꢀC (Scheme 1).
In order to prepare benzo[a]phenazine annulated heterocycles in a greener way, mini-
mizing the reaction temperature, time and amount of catalyst, the reaction of 2-
hydroxy-1,4-naphthalendione, o-phenylenediamine, 4-chlorobenzaldehyde, and malono-
nitrile/dimedone was selected as a model system (Scheme 2). The use of different
amounts of catalyst (10, 20 and 30 mol%) at various temperatures (25, 40, 60, and
80 ꢀC) was investigated (Table 1). The best result was obtained when the reaction was
carried out in the presence of 20 mol% of fulvic acid at 60 ꢀC in H2O, which afforded
the corresponding 3-amino-1-(4-chlorophenyl)-1H-benzo[a]pyrano[2,3-c]phenazine-2-
carbonitrile 7a and 16-(4-chlorophenyl)-3,3-dimethyl-2,3,4,16-tetrahydro-1H-ben-
zo[a]chromeno[2,3-c]phenazin-1-one 8a in 2 h and 3 h with 96% and 94% yields,
respectively (Entries 3 and 5, Table 1).
With optimized conditions we then tested the process for a variety aromatic alde-
hydes including these with electron withdrawing and electron donating groups. In all
cases the products were obtained in good to high yields (Table 2). Aliphatic aldehydes
were unreactive (Entries 14, 15, 30, and 31, Table 2).
We also investigated the recycling of the catalyst under our reaction conditions using
a model reaction of 2-hydroxy-1,4-naphthalendione, o-phenylenediamine, 4-chloroben-
zaldehyde and malononitrile. After completion of the reaction, the crude solid product
was filtered and washed with H2O (2 ꢁ 5 mL). The fulvic acid was removed from the
reaction media by washing with H2O. Since the catalyst is soluble in water, the catalyst
was recovered by evaporation of the water and washed with diethyl ether and reused
for subsequent catalytic runs. The catalytic system worked well up to five catalytic runs
(Figure 2).
In order to assess the efficiency and generality of this methodology, our results were
compared with those of the previously reported methods (Table 3). The present method
was superior to the previous ones with respect to reaction time, yield of the product
and amount of the catalyst.
In conclusion, fulvic acid is a convenient and efficient catalyst for the four-compo-
nent assembling of 2-hydroxy-1,4-naphthalenedione, o-phenylenediamine, aromatic
aldehydes and different C-H acids in H2O at 60 ꢀC in excellent yields. The reaction is

50
A. YAZDANI-ELAH-ABADI ET AL.
Scheme 1. Synthesis of benzo[a]pyrano[2,3-c]phenazine and benzo[a]chromeno[2,3-c]phenazine in
the presence of fulvic acid as catalyst in H2O at 60 ꢀC.
Scheme 2. The model reaction for optimizing conditions for the synthesis of benzo[a]phenazine
annulated heterocycles.
Table 1. Optimization of the reaction conditions for the synthesis of 7a and 8a.
Time (h)
Yield (%)a
Entry
Cat (mol%)
T (ꢀC)
7a
8a
7a
8a
1
2
3
4
5
6
7
20
20
20
20
20
30
10
rt
6
4
3
2
2
2
2
6
4
3
2
2
3
3
NR
74
96
89
96
93
87
NR
69
94
90
91
85
83
40
60
80
60
60
60
aIsolated yields.
performed under mild conditions and may be valuable for diversity-oriented large-scale
processes. The catalyst is inexpensive, clean, safe, nontoxic, and easily obtained and
reused. The procedure offers high yields, operational simplicity, clean reaction condi-
tions, and minimum pollution of the environment, factors which make it a useful and
attractive process for the synthesis of these compounds.

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
51
Table 2. Preparation of benzo[a]phenazine annulated heterocycles in the presence of fulvic acid
(20 mol%) as catalyst at 60 ꢀC in H2O.
Entry
Aldehyde
CH acid
Product
Time (h)
Yield (%)a
MP (Obs) (ꢀC)
MP (Lit) (ꢀC)
1
2
3
4
5
6
7
8
4-ClC6H4
4-NO2C6H4
4-BrC6H4
4-FC6H4
3-CNC6H4
4-Cl-3-NO2C6H3
3-NO2C6H4
2,4-Cl2C6H3
C6H5
4-CH3C6H4
2-CH3OC6H4
3-CH3OC6H4
4-OH-3-CH3OC6H3
n-Heptanal
n-Octanal
5
5
5
5
5
5
5
5
5
5
5
5
5
5
5
6a
6a
6a
6a
6a
6a
6a
6a
6a
6a
6b
6b
6c
6c
6a
6a
7a
7b
7c
7d
7e
7f
7g
7h
7i
7j
7k
7l
7m
–
–
8a
8b
8c
8d
8e
8f
8g
8h
8i
8j
8k
8l
8m
8n
–
2
2
2
2
2
2
2
2
3
3
3
3
4
6
6
3
3
3
3
3.5
3.5
3.5
3.5
3.5
3.5
4
96
95
90
92
91
94
94
92
90
90
87
88
85
NR
NR
94
92
91
93
94
90
88
86
85
83
90
84
92
89
NR
NR
290-291
280-282
285-287
274-275
327-328
295-297
278
309-310
300
291-293
270-272
242-244
249-250
–
288-29126
281-28326
283-28526
274-27626
Present work
Present work
278-27926
308-31030
298-30026
293-29426
270-27226
240-24230
247-24826
–
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
–
–
4-ClC6H4
3-ClC6H4
4-BrC6H4
260-262
251-252
263-264
280
249-250
233-235
207
196-198
241-244
297-299
256-258
245-247
306-307
269-271
–
260-26417
250-25217
260-26217
Present work
Present work
Present work
207-20917
198-20017
242-24428
298-30017
256-25829
244-24629
308-31129
270-27129
–
2,4-Cl2C6H3
2-OH-5-NO2-C6H3
5-Br-2OH-C6H3
4-CH3C6H4
4-CH3OC6H4
3,4-(CH3O)2C6H3
4-OH-3-CH3OC6H3
4-BrC6H4
4-CH3OC6H4
4-ClC6H4
4-CH3C6H4
n-Heptanal
n-Octanal
4
3
4
6
–
6
–
–
aIsolated yields.
Figure 2. The investigation of the recycling of fulvic acid.
Experimental section
All melting points were determined on an Electrothermal 9100 apparatus and are
uncorrected. IR spectra were recorded on a Shimadzu IR-470 spectrometer. Elemental
analyses for C, H, and N were performed using a Costech ECS 4010 CHNS-O analyzer
at the analytical laboratory of Islamic Azad University Yazd Branch. Mass spectra were

52
A. YAZDANI-ELAH-ABADI ET AL.
Table 3. Comparison of the efficiency of fulvic acid with other reported catalysts in literature.
Entry
Product
Catalyst/Condition
Time (min)
Yield (%)
1
2
3
4
5
6
7
8
7b
7b
7b
8a
HOAc/MW26
10 min
600 min
120 min
120 min
180 min
300 min
300 min
150 min
210 min
300 min
300 min
180 min
240 min
270 min
270 min
180 min
180 min
80
60
95
90
94
87
99
81
88
92
95
82
90
86
97
80
92
DABCO (30 mol%)/EtOH, Reflux27
Fulvic acid/H2O, 60 jC (Present work)
p-TSA/PEG-400, 70 jC17
8a
Fulvic acid/H2O, 60 jC (Present work)
H2SO4/EtOH, H2O, 80 jC29
8g
8g
8g
8g
8k
8k
8k
Phosphotungstic acid/EtOH, H2O, 80 jC29
[NMP]H2PO4/80 jC29
9
Fulvic acid/H2O, 60 jC (Present work)
H2SO4/EtOH, H2O, 80 jC29
10
11
12
13
14
15
16
17
Phosphotungstic acid/EtOH, H2O, 80 jC29
[NMP]H2PO4/80 jC29
8k
Fulvic acid/H2O, 60 jC (Present work)
H2SO4/EtOH, H2O, 80 jC29
8m
8m
8m
8m
Phosphotungstic acid/EtOH, H2O, 80 jC29
[NMP]H2PO4/80 jC29
Fulvic acid/H2O, 60 jC (Present work)
recorded on an Agilent Technology (HP) spectrometer operating at an ionization poten-
1
tial of 70 eV. The H nuclear magnetic resonance (NMR) and 13C NMR spectra were
recorded on Bruker DRX-400 Avance instruments with CDCl3 and DMSO-d6 as solv-
ent. Thin-layer chromatography (TLC) was performed on silica-gel Polygram SILG/UV
254 plates using ethyl acetate-n-hexane (1:2) as solvent. All reagents and solvents were
purchased from Merck and Aldrich and used without further purification. Fulvic acid
was prepared according to the reported procedures.36
General procedure for the synthesis of benzo[a]pyrano[2,3-c]phenazine
derivatives (7a-m)
Fulvic acid (20 mol%) was added to a mixture of 2-hydroxynaphthalene-1,4-dione 1
(1 mmol) and o-phenylenediamine 2 (1 mmol) at 60 ꢀC in H2O. After 5 minutes an
orange solid of benzo[a]phenazine 3 was formed. Then, aryl aldehydes 4 (1 mmol), and
malononitrile 5 (1 mmol), were added. The progress of the reaction was monitored by
TLC. After completion of the reaction, the crude solid product was filtered and washed
with H2O (2 ꢁ 5 mL) to remove the catalyst. The resulting product was subsequently
recrystallized from hot ethanol to give the pure solid.
General procedure for the synthesis of benzo[a]chromeno[2,3-c]phenazine
derivatives (8a-n)
To a stirred solution of 2-hydroxynaphthalene-1,4-dione 1 (1 mmol) and o-phenylenedi-
amine 2 (1 mmol) in H2O at 60 ꢀC, fulvic acid (20 mol%) was added. After 5 minutes an
orange solid of benzo[a]phenazine 3 was formed. Then, aryl aldehydes 4 (1 mmol) and
cyclic 1,3-dicarbonyl compounds 6a-c were added. The progress of the reaction was
monitored by TLC. After completion of the reaction, the crude solid product was fil-
tered and washed with H2O (2 ꢁ 5 mL) to separate catalyst. The resulting product was
subsequently recrystallized from hot ethanol to give the pure solid. The analytical and
spectroscopic data for the unknown compounds are as follows.

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
53
3-Amino-1-(3-cyanophenyl)-1H-benzo[a]pyrano[2,3-c]phenazine-2-carbonitrile (7e)
Brown solid; yield 0.387 g (91%); mp 327-328 ꢀC; IR (KBr, cmꢂ1): ꢀmax 3395, 3330,
2900, 2160, 1649, 1608, 1587, 1532, 1491, 1469, 1388, 1335, 1287, 1216, 1153, 1120,
1
1075, 1043, 948, 888, 754; H NMR (400 MHz, DMSO-d6): d 5.61 (s, 1H, CH), 7.50 (s,
2H, NH2), 7.62 (td, J1 ¼ 8.0 Hz, J2 ¼ 1.6 Hz, 1H, Ar-H), 7.80 (td, J1 ¼ 8.0 Hz, J2 ¼
1.6 Hz, 1H, Ar-H), 7.94-8.06 (m, 6H, Ar-H), 8.16-8.18 (m, 1H, Ar-H), 8.30-8.32 (m, 1H,
Ar-H), 8.49 (d, J ¼ 7.6 Hz, 1H, Ar-H), 9.27 (d, J ¼ 8.0 Hz, 1H, Ar-H); 13C NMR
(100 MHz, DMSO-d6): d 37.8, 57.5, 111.6, 112.8, 119.2, 120.4, 122.8, 125.3, 126.1, 129.0,
129.6, 129.7, 130.1, 130.7, 130.8, 131.0, 131.3, 131.9, 133.3, 140.4, 140.5, 141.0, 141.9,
146.9, 147.3, 160.2 ppm. MS (m/z, %): 425 (Mþ, 1).
Anal. Calcd. for C27H15N5O: C, 76.2; H, 3.6; N, 16.5. Found: C, 76.1; H, 3.6; N, 16.3.
3-Amino-1-(4-chloro-3-nitrophenyl)-1H-benzo[a]pyrano[2,3-c]phenazine-2-
carbonitrile (7f)
Brown solid; yield 0.450 g (94%); mp 295-297 ꢀC; IR (KBr, cmꢂ1): ꢀmax 2405, 3332,
2895, 2165, 1655, 1610, 1590, 1525, 1493, 1464, 1374, 1338, 1290, 1217, 1160, 1100,
1
1074, 1045, 949, 834, 753; H NMR (400 MHz, DMSO-d6): d 5.61 (s, 1H, CH), 7.56 (s,
2H, NH2), 7.64 (d, J ¼ 8.4 Hz, 1H, Ar-H), 7.79 (dd, J1 ¼ 8.4 Hz, J2 ¼ 2.0 Hz, 1H, Ar-H),
7.91-8.03 (m, 4H, Ar-H), 8.12-8.15 (m, 1H, Ar-H), 8.20 (d, J ¼ 2.0 Hz, 1H, Ar-H), 8.25-
8.27 (m, 1H, Ar-H), 8.45 (d, J ¼ 7.6 Hz, 1H, Ar-H), 9.21 (d, J ¼ 7.6 Hz, 1H, Ar-H); 13C
NMR (100 MHz, DMSO-d6): d 37.5, 56.9, 112.1, 120.2, 122.6, 123.5, 125.1, 125.6, 125.8,
128.8, 129.4, 130.4, 130.6, 130.9, 131.8, 133.7, 140.1, 140.4, 140.6, 141.7, 146.6, 146.7,
147.6, 160.3 ppm. MS (m/z, %): 479 (Mþ, 4).
Anal. Calcd. for C26H14ClN5O3: C, 65.1; H, 2.9; N, 14.6. Found: C, 65.1; H, 2.8; N, 14.5.
16-(2,4-Dichlorophenyl)-3,3-dimethyl-2,3,4,16-tetrahydro-1H-
benzo[a]chromeno[2,3-c]phenazin-1-one (8d)
Brown solid; yield 0.488 g (93%); mp 280 ꢀC; IR (KBr): ꢀmax ¼ 3395, 2900, 1649, 1611,
1
1588, 1524, 1454, 1362, 1319, 1201, 1162, 1041, 854, 751 cmꢂ1; H NMR (400 MHz,
CDCl3): d ¼ 1.15 (s, 3H, CH3), 1.24 (s, 3H, CH3), 2.33 and 2.43 (AB system, J ¼ 16.4 Hz,
2H, CHAHBCO), 2.81 (s, 2H, CHAHBC(CH3)2), 6.24 (s, 1H, CH), 7.05 (dd, J1 ¼ 8.4 Hz,
J2 ¼ 2.0 Hz, 1H, Ar-H), 7.49 (d, J ¼ 6.8 Hz, 1H, Ar-H), 7.75-7.89 (m, 5H, Ar-H), 8.25-
8.28 (m, 2H, Ar-H), 8.38-8.40 (m, 1H, Ar-H), 9.36-9.38 (m, 1H, Ar-H) ppm; 13C NMR
(100 MHz, CDCl3): d ¼ 27.2, 29.6, 32.2, 32.4, 41.1, 50.8, 113.2, 114.3, 121.9, 125.2, 125.9,
126.3, 128.5, 129.2, 129.3, 129.4, 129.8, 130.8, 132.2, 132.8, 135.1, 140.2, 140.6, 140.8,
141.4, 142.3, 146.9, 163.6, 196.7 ppm. MS (m/z, %): 525 (Mþ, 9).
Anal. Calcd. for C31H22Cl2N2O2: C, 70.9; H, 4.2; N, 5.3. Found: C, 80.1; H, 4.1; N, 5.5.
16-(2-Hydroxy-5-nitrophenyl)-3,3-dimethyl-2,3,4,16-tetrahydro-1H-
benzo[a]chromeno[2,3-c]phenazin-1-one (8e)
Green solid; yield 0.486 g (94%); mp 249-250 ꢀC; IR (KBr): ꢀmax ¼ 3390, 2895, 1647,
1608, 1595, 1515, 1454, 1363, 1335, 1205, 1195, 1034, 804, 752 cmꢂ1 1H NMR
;

54
A. YAZDANI-ELAH-ABADI ET AL.
(400 MHz, CDCl3): d ¼ 1.18 (s, 3H, CH3), 1.26 (s, 3H, CH3), 2.37 and 2.46 (AB system,
J ¼ 16.4 Hz, 2H, CHAHBCO), 2.85 and 2.92 (AB system, J ¼ 17.6 Hz, 2H,
CHAHBC(CH3)2), 6.22 (s, 1H, CH), 7.36 (t, J ¼ 8.0 Hz, 1H, ArH), 7.84-7.94 (m, 5H, Ar-
H, OH), 8.04 (dt, J1 ¼ 8.0 Hz, J2 ¼ 1.6 Hz, 1H, Ar-H), 8.27-8.30 (m, 1H, Ar-H), 8.35
(dd, J1 ¼ 8.0 Hz, J2 ¼ 1.6 Hz, 1H, Ar-H), 8.43-8.46 (m, 1H, Ar-H), 8.52 (t, J ¼ 2.0 Hz,
1H, Ar-H), 9.44 (dd, J1 ¼ 7.6 Hz, J2 ¼ 1.6 Hz, 1H, Ar-H) ppm; 13C NMR (100 MHz,
CDCl3): d ¼ 27.3, 29.6, 32.4, 34.0, 41.2, 50.8, 113.7, 114.5, 121.4, 122.0, 124.4, 125.3,
126.0, 128.4, 128.6, 129.1, 129.3, 129.7, 129.9, 130.1, 130.9, 135.4, 140.5, 140.8, 141.1,
142.2, 146.8, 147.1, 147.9, 164.1, 196.7 ppm. MS (m/z, %): 517 (Mþ, 23).
Anal. Calcd. for C31H23N3O5: C, 71.9; H, 4.5; N, 8.1. Found: C, 71.7; H, 4.6; N, 8.1.
16-(5-Bromo-2-hydroxyphenyl)-3,3-dimethyl-2,3,4,16-tetrahydro-1H-
benzo[a]chromeno[2,3-c]phenazin-1-one (8f)
Yellow solid; yield 0.495 g (90%); mp 233-235 ꢀC; IR (KBr): ꢀmax ¼ 3360, 2910, 1631,
1610, 1588, 1521, 1461, 1367, 1337, 1221, 1172, 1025, 807, 755 cmꢂ1 1H NMR
;
(400 MHz, CDCl3): d ¼ 1.12 (s, 3H, CH3), 1.18 (s, 3H, CH3), 2.31-2.42 (m, 2H,
CHAHBCO), 2.84-295 (m, 2H, CHAHBC(CH3)2), 6.21 (s, 1H, CH), 7.38 (t, J ¼ 7.6 Hz,
1H, ArH), 7.81-8.06 (m, 5H, Ar-H, OH), 8.00-8.06 (m, 1H, Ar-H), 8.26-8.37 (m, 2H,
Ar-H), 8.39-8.44 (m, 1H, Ar-H), 8.51-8.55 (m, 1H, Ar-H), 9.41-9.46 (m, 1H, Ar-H)
ppm; 13C NMR (100 MHz, CDCl3): d ¼ 27.0, 27.3, 29.7, 32.5, 41.1, 50.6, 114.8, 118.2,
120.7, 122.0, 125.4, 126.4, 127.6, 128.6, 128.9, 129.2, 129.4, 129.9, 130.3, 130.4, 130.6,
130.9, 131.0, 134.2, 140.2, 140.5, 141.4, 153.2, 164.5, 196.5 ppm. MS (m/z, %): 550
(Mþ, 12).
Anal. Calcd. for C31H23BrN2O3: C, 67.5; H, 4.2; N, 5.1. Found: C, 67.6; H, 4.0; N, 5.3.
Acknowledgment
We gratefully acknowledge financial support from the Research Council of Young Researchers
and Elite Club, Islamic Azad University, Yazd Branch, Yazd, Iran.
References
1. N. Senesi, Analytica Chimica Acta, 232, 51 (1990). doi:10.1016/S0003-2670(00)81225-8
2. P. Anastas and N. Eghbali, Chem. Soc. Rev., 39, 301 (2010). doi:10.1039/B918763B
3. P. T. Anastas and J. C. Warner, Green Chemistry: Theory and Practice; Oxford University
Press: New York, 1998, p. 30.
4. W. Leitner, Green Chem., 11, 603 (2009).
5. N. Hazeri, M. T. Maghsoodlou, F. Mir, M. Kangani, H. Saravani and E. Molashahi, Chin. J.
Catal., 35, 391 (2014). doi:10.1016/S1872-2067(14)60003-6
6. M. T. Maghsoodlou, N. Hazeri, M. Lashkari, F. Nejad Shahrokhabadi, B. Naghshbandi, M. S.
Kazemi-doost, M. Rashidi, F. Mir, M. Kangani and S. Salahi, Res. Chem. Intermed., 41, 6985
(2015). doi:10.1007/s11164-014-1793-4
7. J. McNulty and P. Das, Eur. J. Org. Chem., 24, 4031 (2009). doi:10.1002/ejoc.200900634
8. J. McNulty, P. Das and D. McLeod, Chem. –Eur. J., 16, 6756 (2010). doi:10.1002/chem.
201000438
9. S. Narayan, J. Muldoon, M. G. Finn, V. V. Fokin, H. C. Kolb and K. B. Sharpless, Angew.
Chem. Int. Ed., 21, 3157 (2005). doi:10.1002/anie.200590069

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL
55
10. M. B. Smith and J. March, March’s Advanced Organic Chemistry: Reactions, Mechanisms, and
Structure, John Wiley & Sons: New York, 2007, passim.
11. R. Breslow, In Organic Reactions in Water, M. Lindstrom, Ed.; Blackwell: Oxford, 2007, pp.
1–28.
12. R. Breslow, Acc. Chem. Res., 24, 159 (1991). doi:10.1021/ar00006a001
13. G. Khanna, A. Chaudhary and J. M. Khurana, Tetrahedron Lett., 55, 6652 (2014). doi:10.
1016/j.tetlet.2014.10.067
14. B. Jiang, S. J. Tu, P. Kaur, W. Wever and G. Li, J. Am. Chem. Soc., 131, 11660 (2009). doi:
10.1021/ja904011s
15. J. M. Knapp, J. S. Zhu, D. J. Tantillo and M. J. Kurth, Angew. Chem. Int. Ed., 51, 10588
(2012). doi:10.1002/anie.201204633
16. M. Li, H. Cao, Y. Wang, X. L. Lv and L. R. Wen, Org. Lett., 14, 3470 (2012). doi:10.1021/
ol301441v
17. J. M. Khurana, A. Chaudhary, A. Lumb and B. Nand, Green Chem., 14, 2321 (2012). doi:10.
1039/c2gc35644a
18. J. B. Laursen and J. Nielsen, Chem. Rev., 104, 1663 (2004). doi:10.1021/cr020473j
19. A. Price-Whelan, L. E. P. Dietrich and D. K. Newman, Nat. Chem. Biol., 2, 71 (2006). doi:10.
1038/nchembio764
20. D. V. Mavrodi, W. Blankenfeldt and L. S. Thomashow, Annu. Rev. Phytopathol., 44, 417
(2006). doi:10.1146/annurev.phyto.44.013106.145710
21. Y. Liu, L. Jin and J. Liu, J. Heterocycl. Chem., 54, 1931 (2017). doi:10.1002/jhet.2788
22. A. Mandal, S. Mondal, A. Jana, S. Manna S. Ali and S. Samanta, J. Heterocycl. Chem., 54,
2529 (2017). doi:10.1002/jhet.2832
23. D. V. Mavrodi, T. L. Peever, O. V. Mavrodi, J. A. Parejko, J. M. Raaijmakers, P. Lemanceau,
S. Mazurier, L. Heide, W. Blankenfeldt, D. M. Weller and L. S. Thomashow, Appl. Environ.
Microbiol., 76, 866 (2010). doi:10.1128/AEM.02009-09
24. H. J. Lee, J. S. Kim, S. Y. Park, M. E. Suh, H. J. Kim, E. K. Seo and C. O. Lee, Bioorg. Med.
Chem., 12, 1623 (2004). doi:10.1016/j.bmc.2004.01.029
25. J. S. Kim, H. K. Rhee, H. J. Park, I. K. Lee, S. K. Lee, M. E. Suh, H. J. Lee, C. -K. Ryu and
H. Y. Park Choo, Bioorg. Med. Chem., 15, 451 (2007). doi:10.1016/j.bmc.2006.09.040
26. S. L. Wang, F. Y. Wu, C. Cheng, G. Zhang, Y. P. Liu, B. Jiang, F. Shi and S. J. Tu, ACS
Comb. Sci., 13, 135 (2011). doi:10.1021/co1000376
27. A. Hasaninejad and S. Firoozi, Mol. Divers., 17, 499 (2013). doi:10.1007/s11030-013-9446-x
28. P. Saluja, A. Chaudhary and J. M. Khurana, Tetrahedron Lett., 55, 3431 (2014). doi:10.1016/j.
tetlet.2014.04.072
29. M. Rajeswari, G. Khanna, A. Chaudhary and J. M. Khurana, Synth. Commun., 45, 1426
(2015). doi:10.1080/00397911.2015.1024324
30. A. Yazdani Elah Abadi, M. T. Maghsoodlou, R. Heydari and R. Mohebat, Res. Chem.
Intermed., 42, 1227 (2016). doi:10.1007/s11164-015-2083-5
31. R. Mohebat, A. Yazdani Elah Abadi, M. T. Maghsoodlou and M. Mohammadi, Res. Chem.
Intermed., 42, 5915 (2016). doi:10.1007/s11164-015-2413-7
32. R. Mohebat, A. Yazdani Elah Abadi, M. T. Maghsoodlou, M. Mohammadi and R. Heydari,
Res. Chem. Intermed., 42, 7121 (2016). doi:10.1007/s11164-016-2522-y
33. F. NooriSadeh, M. T. Maghsoodlou, N. Hazeri and M. Kangani, Res. Chem. Intermed., 41,
5907 (2015). doi:10.1007/s11164-014-1710-x
34. M. Kangani, M. T. Maghsoodlou and N. Hazeri, Chin. Chem. Lett., 27, 66 (2016). doi:10.
1016/j.cclet.2015.07.025
35. M. Kangani, N. Hazeri, M. T. Mghsoodlou, S. M. Habibi-Khorasani and S. Salahi, Res. Chem.
Intermed., 41, 2513 (2015). doi:10.1007/s11164-013-1365-z
36. R. S. Swift, Natur. Org. Matt. Char., 1018 (1996).