A rapid and efficient domino protocol for the synthesis of functionalized benzo[a]pyrano[2,3-c]phenazine and benzo[f]pyrano[2,3-h]quinoxaline derivatives

Article abstract of DOI:10.1007/s11164-016-2437-7

Benzo[a]pyrano[2,3-c]phenazine and benzo[f]pyrano[2,3-h]quinoxaline derivatives were synthesized via a one-pot, two-step procedure from a three-component condensation reaction of 2-hydroxynaphthalene-1,4-dione, 1,2-diamines, and tetracyanoethylene in the presence of pyridine as an efficient catalyst. This novel procedure has the advantages of operational simplicity, short reaction times, easy work-up, avoiding costly syntheses, and the products do not require further purification, which provides an efficient and economical method for the synthesis of related products in excellent yields.

Full text of DOI:10.1007/s11164-016-2437-7

Res Chem Intermed
DOI 10.1007/s11164-016-2437-7
A rapid and efficient domino protocol for the synthesis
of functionalized benzo[a]pyrano[2,3-c]phenazine
and benzo[f]pyrano[2,3-h]quinoxaline derivatives
1
2
•
Razieh Mohebat
Malek-Taher Maghsoodlou
•
Afshin Yazdani Elah Abadi
2
Received: 25 December 2015 / Accepted: 11 January 2016
Ó Springer Science+Business Media Dordrecht 2016
Abstract Benzo[a]pyrano[2,3-c]phenazine and benzo[f]pyrano[2,3-h]quinoxaline
derivatives were synthesized via a one-pot, two-step procedure from a three-com-
ponent condensation reaction of 2-hydroxynaphthalene-1,4-dione, 1,2-diamines,
and tetracyanoethylene in the presence of pyridine as an efficient catalyst. This
novel procedure has the advantages of operational simplicity, short reaction times,
easy work-up, avoiding costly syntheses, and the products do not require further
purification, which provides an efficient and economical method for the synthesis of
related products in excellent yields.
Keywords Multi-component domino reactions (MDRs) Á Tetracyanoethylene Á
Pyridine Á Benzo[a]pyrano[2,3-c]phenazine Á Benzo[f]pyrano[2,3-h]quinoxaline
Introduction
Synthesis of polyfunctionalized heterocyclic compounds from readily available
starting materials in a cost- and time-effective manner has received significant
attention in organic synthesis due to their extensive applications in pharmaceuticals,
agrochemicals and in materials sciences [1–4]. In this context, multi-component
domino reactions (MDRs), in which more than two components are combined in a
Electronic supplementary material The online version of this article (doi:10.1007/s11164-016-2437-7)
contains supplementary material, which is available to authorized users.
&
Razieh Mohebat
raziehmohebat@yahoo.com; mohebat@iauyazd.ac.ir
1
2
Department of Chemistry, Yazd Branch, Islamic Azad University, P.O. Box 89195-155,
Yazd, Iran
Department of Chemistry, Faculty of Science, University of Sistan and Baluchistan,
Zahedan, Iran
123

R. Mohebat et al.
single synthetic operation, have been extensively used as a powerful strategy in the
synthesis of complex heterocyclic molecules due to their advantages, such as higher
productivity, simple procedures, facile execution, lower costs, minimum waste
production, structural diversity, shorter reaction times, environmental friendliness,
atom economy, high selectivity and allowing savings of both solvents and reagents
[
5–10].
Heterocycles with phenazines [11], quinoxalines [12] and pyrans [13] moieties
are important targets in the synthetic organic chemistry and they have attracted great
attention in drug discovery.
Phenazine systems are an important class of aza-polycyclic compounds that exist
in natural and synthetic products [14–17] and have been demonstrated to possess a
myriad of biological functions, including antimalarial [18, 19], fungicidal [20, 21],
trypanocidal [22], antiplatelet [23], and antitumor [24] activities. Some
benzo[a]phenazines that have been formed from napthoquinone and phenazin are
dual inhibitors of topoisomerase I and II, two key enzymes that affect the topology
of DNA at different points in the cell cycle [25].
Also, quinoxaline compounds and its derivatives are nitrogen-containing
heterocycles that have attracted much attention due to numerous and varied
applications such as antibacterial [26], antidepressant [27], antitumor agents [28],
electroluminescent materials [29], organic semiconductors [30] and useful inter-
mediates in organic synthesis [31, 32].
Scheme 1 Synthesis of benzo[a]pyrano[2,3-c]phenazine and benzo[f]pyrano[2,3-h]quinoxaline
derivatives
1
23

A rapid and efficient domino protocol for the synthesis of…
In addition, pyrans are important core unit in a number of natural products [33,
4] and these compounds are significant because of their useful biological activities,
3
such as spasmolytic, diuretic, anticoagulant, anticancer, and anti-anaphylactic
activities [35–38].
Considering the importance of phenazine, quinoxaline and pyran derivatives and
in continuation of our research on multi-component reactions [39–43], in this paper
we would like to report a one-pot, domino protocol from the condensation reaction
of 2-hydroxynaphthalene-1,4-dione 1 and 1,2-diamine 2 (activated CH-acids 3a–f)
with tetracyanoethylene 4 as a strongly electrophilic reagent by using pyridine as
catalyst that afforded the corresponding pyran annulated heterocyclic systems 5a–
f (Scheme 1).
Experimental
General
All melting points were determined on an Electrothermal 9100 apparatus and are
uncorrected. Elemental analyses were performed at the analytical laboratory of
Science and Researches Unit of Islamic Azad University. Mass spectra were
recorded on an Agilent Technology (HP) spectrometer operating at an ionization
potential of 70 eV. IR spectra were recorded on a Shimadzu IR-470 spectrometer.
1
13
The H nuclear magnetic resonance (NMR) and C NMR spectra were recorded on
Bruker DRX-400 Avance instruments with deuterated dimethyl sulfoxide (DMSO-
d6) as solvent. Thin-layer chromatography (TLC) was performed on silica-gel
Polygram SILG/UV 254 plates. All reagents and solvent were purchased from
Merck and Aldrich and used without further purification.
General procedure for the synthesis of benzo[a]pyrano[2,3-c]phenazine
and benzo[f]pyrano[2,3-h]quinoxaline derivatives (5a–f)
Initially, 2-hydroxynaphthalene-1,4-dione 1 (1 mmol) and 1,2-diamine 2 (1 mmol)
were added to a 25-mL round-bottomed flask containing ethanol (10 mL) as solvent.
The flask was fitted with a condenser, and the resulting mixture was heated to reflux
under stirring. After the required time (5–10 min) for the formation of correspond-
ing phenazine or quinoxaline 3, tetracyanoethylene 4 (1 mmol), and pyridine
(
10 mol%) as catalyst were added into the reaction mixture and stirred for
0–60 min at room temperature. Upon completion of the reaction, monitored by
3
TLC, the solid product was filtered and washed twice with EtOH (2 9 5 mL), dried,
and subsequently recrystallized from hot ethanol. The spectral and analytical data
are presented below:
123

R. Mohebat et al.
3
-Amino-1H-benzo[a]pyrano[2,3-c]phenazine-1,1,2-tricarbonitrile (5a)
-
cm ): 3405
1
Brown solid; yield 0.355 g (95 %), mp 246–248 °C; IR (KBr) (m
max
1
and 3300 (NH ), 2200 (CN); H NMR (400 MHz, DMSO-d ): d 8.02–8.09 (m, 4H,
2
6
Ar–H), 8.32–8.34 (m, 1H, Ar–H), 8.36–8.40 (m, 2H, Ar–H), 8.60 (s, 2H, NH ),
2
1
3
9
1
1
.22–9.25 (m, 1H, Ar–H) ppm; C NMR (100 MHz, DMSO-d ): d 33.2, 50.6,
6
00.0, 115.0, 117.2, 123.6, 124.8, 125.3, 128.9, 129.7, 131.4, 131.5, 131.6, 131.7,
?
32.3, 138.8, 140.1, 141.2, 141.3, 147.6, 159.9 ppm; MS (m/z, %): 374 (M , 12);
Anal. Calcd for C H N O: C, 70.58; H, 2.69; N, 22.45 %. Found: C, 70.39; H,
2
22 10 6
.50; N, 22.57 %.
-Amino-12-methyl-1H-benzo[a]pyrano[2,3-c]phenazine-1,1,2-tricarbonitrile (5b)
3
-
1
cm ): 3405 and
Yellow solid; yield 0.356 g (92 %), mp 240 °C; IR (KBr) (m
max
1
3
300 (NH ), 2180 (CN); H NMR (400 MHz, DMSO-d ): d 2.68 (s, 3H, CH ), 7.86
2
6
3
(
H), 8.17–8.21 (m, 1H, Ar–H), 8.30–8.34 (m, 1H, Ar–H), 8.57 (s, 2H, NH ),
d, 1H, J = 7.2 Hz, Ar–H), 7.96–7.99 (m, 2H, Ar–H), 8.07 (d, 1H, J = 9.6 Hz, Ar–
2
1
3
9
9
1
.11–9.15 (m, 1H, Ar–H) ppm; C NMR (100 MHz, DMSO-d ): d 21.0, 33.3, 54.3,
6
9.0, 114.0, 116.2, 122.5, 124.1, 126.3, 127.0, 127.5, 128.3, 130.1, 130.4, 133.3,
?
33.8, 137.6, 138.9, 140.3, 141.3, 142.1, 158.8 ppm; MS (m/z, %): 388 (M , 8);
Anal. Calcd for C H N O: C, 71.13; H, 3.11; N, 21.64 %. Found: C, 71.30; H,
2
23 12 6
.92; N, 21.59 %.
3
-Amino-11-nitro-1H-benzo[a]pyrano[2,3-c]phenazine-1,1,2-tricarbonitrile (5c)
-
cm ): 3410
1
Brown solid; yield 0.377 g (90 %), mp 269–271 °C; IR (KBr) (m
max
1
and 3305 (NH ), 2185 (CN); H NMR (400 MHz, DMSO-d ): d 8.01–8.08 (m, 2H,
2
6
Ar–H), 8.36 (d, 1H, J = 8.4 Hz, Ar–H), 8.48 (dd, 1H, J = 3.6 Hz, J = 9.6 Hz,
Ar–H), 8.62 (td, 1H, J = 2.0 Hz, J = 9.2 Hz, Ar–H), 8.74 (s, 2H, NH ), 8.93 (d,
1
2
1
2
2
1
H, J = 2.4 Hz, Ar–H), 9.12–9.16 (m, 1H, Ar–H) ppm; C NMR (100 MHz,
3
1
DMSO-d ): d 33.7, 54.8, 99.4, 114.2, 116.5, 123.4, 124.1, 124.4, 125.4, 130.3,
6
1
30.4, 131.2, 131.5, 131.7, 139.0, 140.2, 140.6, 141.3, 142.6, 148.1, 158.1 ppm; MS
?
m/z, %): 419 (M , 11); Anal. Calcd for C H N O : C, 63.01; H, 2.16; N,
(
2
2 9 7 3
2
3.38 %. Found: C, 63.14; H, 2.30; N, 23.32 %.
3
-Amino-1H-benzo[f]pyrano[2,3-h]pyrido[3,2-b]quinoxaline-1,1,2-tricarbonitrile
5d)
(
-
1
Brown solid; yield 0.322 g (86 %), mp 258–260 °C; IR (KBr) (mmax cm ): 3395
1
and 3308 (NH ), 2180 (CN); H NMR (400 MHz, DMSO-d ): d 7.82–7.95 (m, 2H,
2
6
Ar–H), 8.00–8.02 (m, 1H, Ar–H), 8.20 (d,1H, J = 8.0 Hz, Ar–H), 8.58 (s, 2H,
NH ), 8.70 (d,1H, J = 6.8 Hz, Ar–H), 8.89–9.00 (m,1H, Ar–H), 9.32 (d,1H,
2
1
3
J = 8.0 Hz, Ar–H) ppm; C NMR (100 MHz, DMSO-d ): d 33.4, 51.7, 100.2,
6
1
15.3, 122.2, 123.1, 125.3, 126.2, 129.6, 129.9, 130.3, 130.7, 131.1, 131.7, 136.1,
?
41.4, 141.7, 142.0, 148.0, 159.6 ppm; MS (m/z, %): 375 (M , 10); Anal. Calcd
1
1
23

A rapid and efficient domino protocol for the synthesis of…
for C H N O: C, 67.20; H, 2.42; N, 26.12 %. Found: C, 67.28; H, 2.61; N,
2
1 9 7
2
6.26 %.
7
-Amino-2H-benzo[f]pyrano[2,3-h]quinoxaline-5,5,6(3H)-tricarbonitrile (5e)
-
cm ): 3370
1
Brown solid; yield 0.283 g (87 %), mp 279–281 °C; IR (KBr) (m
max
1
and 3305 (NH ), 2180 (CN); H NMR (400 MHz, DMSO-d ): d 3.50–3.95 (m, 4H,
2
6
2
9
5
1
6
CH ), 7.79–7.98 (m, 2H, Ar–H), 8.34–8.39 (m, 1H, Ar–H), 8.75 (s, 2H, NH ),
2 2
1
3
.10–9.13 (m, 1H, Ar–H) ppm; C NMR (100 MHz, DMSO-d ): d 32.5, 45.2, 46.6,
6
1.7, 100.9, 116.0, 117.7, 125.2, 127.0, 129.8, 130.7, 131.9, 132.3, 134.0, 140.6,
?
49.6, 158.0 ppm; MS (m/z, %): 326 (M , 5); Anal. Calcd for C H N O: C,
1
8 10 6
6.25; H, 3.09; N, 25.75 %. Found: C, 66.38; H, 3.25; N, 25.56 %.
-Amino-5H-benzo[f]pyrano[2,3-h]quinoxaline-2,3,5,5,6-pentacarbonitrile (5f)
7
-
1
cm ): 3370
Brown solid; yield 0.314 g (84 %), mp 262–264 °C; IR (KBr) (m
max
1
and 3312 (NH ), 2205 (CN); H NMR (400 MHz, DMSO-d ): d 8.12–8.16 (m, 2H,
2
6
Ar–H), 8.44 (d, 1H, J = 7.2 Hz, Ar–H), 8.70 (s, 2H, NH ), 9.07 (d, 1H, J = 7.2 Hz,
1
2
3
Ar–H) ppm; C NMR (100 MHz, DMSO-d ): d 33.6, 51.2, 100.6, 115.2, 116.0,
6
1
1
6
17.9, 124.9, 126.7, 127.0, 129.8, 130.8, 131.9, 132.2, 133.9, 134.4, 139.8, 140.7,
?
51.3, 160.6 ppm; MS (m/z, %): 374 (M , 9); Anal. Calcd for C H N O: C,
4.17; H, 1.62; N, 29.94 %. Found: C, 64.30; H, 1.50; N, 29.81 %.
2
0 6 8
Results and discussion
Benzo[a]pyrano[2,3-c]phenazine and benzo[f]pyrano[2,3-h]quinoxaline derivatives
can be synthesized via a two-step procedure. In the first step, 2-hydroxynaph-
thalene-1,4-dione 1 (1 mmol) and 1,2-diamine (2a–f) (1 mmol) were added to a
2
5-mL round-bottomed flask containing ethanol as solvent under reflux conditions
to form the corresponding phenazine or quinoxaline (3a–f). The second step
involves the reaction between the products (3a–f) of the first step with tetracya-
noethylene (4) (1 mmol) in the presence of various catalysts such as pyridine to
form products (5a–f) at ambient temperature.
To discover the best reaction conditions for the synthesis of the expected
products, the one-pot multi-component reaction of 2-hydroxynaphthalene-1,4-dione
(
1 mmol), benzene-1,2-diamine (1 mmol) and tetracyanoethylene (1 mmol) was
selected as the model reaction and the yield and reaction time were monitored in the
presence of various catalytic systems and different molar ratios of the catalyst. The
obtained results have been summarized in Table 1, from which it can be seen that a
higher yield (95 %) was obtained when the reaction was carried out in the presence
of 10 mol% of pyridine in a shorter reaction time (30 min) (Table 1, entry 5).
As shown in Table 1, when using quinoline, isoquinoline and triphenylphosphine
instead of pyridine under the same conditions produced similar results; however, the
reaction yield is lower than pyridine. This may be explained by the basicity of the
quinoline, isoquinoline and triphenylphosphine being weaker than pyridine.
123

R. Mohebat et al.
Table 1 Condensation reaction
between benzo[a]phenazin-5-ol
a
Entry
Catalyst (mol%)
Time (min)
Yield (%)
(
3a) and tetracyanoethylene in
1
2
3
4
5
6
7
8
9
Pyridine (5)
30
30
30
30
30
60
60
60
60
60
84
the presence of various catalysts
and different molar ratios of
catalyst
Quinoline (10)
Isoquinoline (10)
78
81
PPh
3
(10)
79
Pyridine (10)
95
Quinoline (20)
Isoquinoline (20)
87
89
PPh
3
(20)
87
Pyridine (20)
No catalyst
96
1
0
Trace
a
Isolated yields
Table 2 Synthesis of
a
Entry
Diamine
Product
Time (min)
Yield (%)
benzo[a]pyrano[2,3-c]phenazine
and benzo[f]pyrano[2,3-
h]quinoxaline derivatives in the
presence of pyridine (10 mol%)
as catalyst
1
2
3
4
5
6
2a
2b
2c
2d
2e
2f
5a
5b
5c
5d
5e
5f
30
45
45
60
60
60
95
92
90
86
87
84
a
Isolated yields
To show the role of pyridine, we investigated the reaction under identical
conditions without the presence of pyridine and only a trace amount of the desired
product was obtained.
Using these optimized reaction conditions, the scope and efficiency of the
reaction were explored for the synthesis of benzo[a]pyrano[2,3-c]phenazine and
benzo[f]pyrano[2,3-h]quinoxaline derivatives. The results are summarized in
1
Table 2. All the products are new compounds that were characterized by IR, H
1
NMR, C NMR spectra.
3
The mechanism for the formation of the products is proposed in Scheme 2. On
the basis of this mechanism, at first, 2-hydroxynaphthalene-1,4-dione 1 tautomerizes
to intermediate 6. The primary condensation of 6 with 1,2-diamine 2 gives
compound 7, which in tautomerism equilibrium helps to prepare compound 3. Then,
based on the nucleophilicity of pyridine, the nucleophilic addition of pyridine to the
electron-deficient tetracyanoethylene 4 and subsequent protonation in the presence
of compound 3 gives intermediate 8, followed by the attack of the anion on the
cation part of intermediate 8 to form the product 6 via intramolecular cyclization
and a tautomeric proton shift (Scheme 2).
We checked the reaction of benzo[a]phenazin-5-ol derivatives (3a–c) and
tetracyanoethylene in the presence of bases such as Na CO and NaOH. As
2
3
indicated in Table 3, we obtained the desired product; however, the reaction yield
was considerably decreased.
1
23

A rapid and efficient domino protocol for the synthesis of…
Scheme 2 Proposed mechanism based on nucleophilicity of pyridine for the synthesis of
benzo[a]pyrano[2,3-c]phenazine and benzo[f]pyrano[2,3-h]quinoxaline derivatives
Table 3 Condensation reaction
between benzo[a]phenazin-5-ol
derivatives (3a–c) and
a
Entry Diamine Catalyst (30 mol%) Time (min) Yield (%)
1
2
3
4
5
6
2a
2a
2b
2b
2c
2c
Na
2
CO
3
3
3
120
120
120
120
120
120
55
50
47
44
48
40
tetracyanoethylene in the
presence of Na
as catalyst
2
CO
3
and NaOH
NaOH
Na CO
2
NaOH
Na
2
CO
NaOH
a
Isolated yields
Since the reaction works in the presence of bases such as Na CO and NaOH, this
2
3
suggests that the pyridine acts not only as a nucleophile but can also perform a base
role, which the nucleophilicity of it is preferred to its basicity.
The proposed mechanism based on the basicity of pyridine is provided in
Scheme 3.
123

R. Mohebat et al.
Scheme 3 Proposed mechanism based on the basicity of pyridine for the formation of
benzo[a]pyrano[2,3-c]phenazine and benzo[f]pyrano[2,3-h]quinoxaline derivatives
Conclusions
In summary, we have developed an efficient multi-component domino reaction for
the synthesis of functionalized benzo[a]pyrano[2,3-c]phenazine and benzo[f]pyr-
ano[2,3-h]quinoxaline derivatives in excellent yields and purities with short reaction
times, less than 60 min, from readily available starting materials by using a
minimum amount of pyridine as an effective catalyst. The synthetic procedure has a
number of advantages such as: mild reaction conditions, convenient one-pot
operation, excellent chemo- and regioselectivities, and atom economy, which
together make a useful and attractive process for synthesis of these heterocyclic
compounds. In addition, the synthetic procedure is straightforward, avoiding costly
syntheses and hazardous organic solvents. Finally, our work is expected to find
applications in the combinatorial synthesis of biologically active compounds, since
phenazine, quinoxaline and pyran motifs have a wide spectrum of biological
activities.
1
23

A rapid and efficient domino protocol for the synthesis of…
Acknowledgments We gratefully acknowledge financial support from the Research Council of the
Islamic Azad University of Yazd and the University of Sistan and Baluchestan.
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