Application of metalloporphyrins as new catalysts for the efficient, mild and regioselective synthesis of quinoxaline derivatives

Article abstract of DOI:10.1142/S108842461000294X

A simple, highly efficient and green procedure for the condensation of aryl and alkyl 1,2-diamines with α-diketones in the presence of catalytic amounts of metalloporphyrins at room temperature is described. Using this method, quinoxaline derivatives as biologically interesting compounds are produced in high to excellent yields and short reaction times. In this report, the effects of central metal in porphyrin core and substituents on tetraphenylporphyrin skeleton have been studied.

Full text of DOI:10.1142/S108842461000294X

Journal of Porphyrins and Phthalocyanines
J. Porphyrins Phthalocyanines 2010; 14: 1052–1058
DOI: 10.1142/S108842461000294X
Published at http://www.worldscinet.com/jpp/
Application of metalloporphyrins as new catalysts for the
efficient, mild and regioselective synthesis of quinoxaline
derivatives
Khosro Mohammadi*, Alireza Hasaninejad, Mahmud Niad and Mojtaba Najmi
Chemistry Department, Faculty of Sciences, Persian Gulf University, Bushehr 75169, Iran
Received 9 June 2010
Accepted 12 December 2010
ABSTRACT: A simple, highly efficient and green procedure for the condensation of aryl and alkyl 1,2-
diamines with α-diketones in the presence of catalytic amounts of metalloporphyrins at room temperature
is described. Using this method, quinoxaline derivatives as biologically interesting compounds are
produced in high to excellent yields and short reaction times. In this report, the effects of central metal in
porphyrin core and substituents on tetraphenylporphyrin skeleton have been studied.
KEYWORDS: metalloporphyrin, quinoxaline, 1,2-diamine, α-diketone, catalyst.
Thecondensationof1,2-diamineswith1,2-diketoneshas
INTRODUCTION
been used as a useful protocol for the synthesis of quinoxa-
Metalloporphyrins have been the subject of many stud-
lines. For this transformation, several catalysts and reagents
ies because these complexes show wide applicability and
havebeenreported,including(NH ) Mo O ·4H O[17],sul-
4
6
7
24
2
are now used as the catalysts for a variety of photosensitiz-
ers [1], redox catalysts [2], hydroxylation and epoxidation
of hydrocarbon compounds [3, 4], aziridination of olefins
famicacid[18],oxalicacid[19],polianiline-sulfatesalt[20]
and iodine in DMSO [21]. Other methods which have been
applied for the synthesis of quinoxaline derivatives include
heteroannulation of nitroketone N,S-aryliminoacetals with
[5], oxidation of sulfides to sulfones [6], hydroxylation
of aromatic compounds [7], asymmetric carbon-hydrogen
bond formation [8], oxidative carbonylation of amines
POCl [22], bi-catalyzed oxidative coupling of epoxides
3
with ene-1,2-diamines [23] and cyclization of α-arylimino
oximes of α-dicarbonyl compounds [24]. However, many
of the reported protocols are associated with one or more
of the following disadvantages: need for anhydrous con-
ditions, harsh reaction conditions, the use of expensive
reagents, prolonged reaction times, moderate yields and no
agreement with the green chemistry protocols. Therefore,
development of an efficient, cheap, simple and environ-
mentallyfriendlymethodforthepreparationofquinoxaline
derivatives is desirable. Furthermore, no catalytic protocol
for the synthesis of quinoxalines in the presence of metal-
loporphyrins has been reported in the literature so far.
In this study, we wish to introduce a novel method for
the synthesis of quinoxaline derivatives in the presence
of metalloporphyrins as catalyst at room temperature
(Scheme 1).
[
9], silylation of hydroxy groups [10] and ring opening of
epoxides [11]. Nowadays, finding a new catalytic activity
of metalloporphyrins is more fascinating for chemists.
Quinoxaline derivatives are an important class of
nitrogen-containing heterocycles in medicinal chemistry
as they have various biological activities, such as anti-
mycobacterial [12], antidepressant [13], and antitumor
drugs [14]. They have been also used as building blocks
for the synthesis of organic semiconductors [15]. More-
over, these compounds have been applied for the prepara-
tion of various dyes [16].
*
Correspondence to: Khosro Mohammadi, email: khmohammadi@
pgu.ac.ir and khmohammadi@yahoo.com, tel: +98 7714-222-
40, fax: +98 7714-541-494
3
Copyright © 2010 World Scientific Publishing Company

APPꢁICAꢂIOꢃ Oꢄ ꢀꢅꢂAꢁꢁOPOꢆPꢇꢈꢆIꢃS AS ꢃꢅW CAꢂAꢁꢈSꢂS ꢄOꢆ ꢂꢇꢅ ꢅꢄꢄICIꢅꢃꢂ 1053
O
O
Ph
Ph
N
Ph
Ph
NH2
NH2
Mn+(TPP)Cln-2 (10 mol.%)
+
H O/EtOH (3:1 v/v), rt
2
N
1
2
3a
Scheme 1. Condensation of benzene-1,2-diamine with benzil
Table 1. The reaction of benzene-1,2-diamine (1.1 mmol) with
benzil (1 mmol) in the presence of different metalloporphyrins
In the presence of other metalloporphyrins, the reaction
times were longer and the yields of quinoxalines were
low. A control with porphyrin free base has been shown in
Table 1, entry 9 and these data show that central metal is
essential for catalytic activity of porphyrin. Moreover, to
clarify the effect of the porphyrin catalyst on the reaction,
the model reaction was examined in the absence of the cat-
alyst and the yield of quinoxaline was low after a long time
(
10 mol %) in EtOH/H O (1/3) (4 mL)
2
a
Entry
Catalyst
Time (h)
Yield (%)
1
2
3
4
5
6
7
8
9
Cr(TPP)Cl
Mn(TPP)Cl
Fe(TPP)Cl
Co(TPP)Cl
Co(TPP)
Ni(TPP)
Cu(TPP)
Zn(TPP)
TPP
2.0
3.0
3.0
1.5
2.5
2.0
2.5
2.5
4.0
4.0
65
70
70
75
60
60
55
60
32
25
(25% of quinoxaline 3a after 4 h) (Table 1, entry 10).
Due to the conjugation effect, either electron density
or electron withdrawing groups of the para positions of
four phenyls around the porphyrin rings of the positions
of 5, 10, 15 and 20 strongly influence the catalytic activi-
ties of metalloporphyrins. To obtain information on the
III
catalytic activities, 12 kinds of Co -porphyrins catalysts
were also examined in the formation of quinoxaline 3a.
According to the results from Table 2, no significant cor-
relation between the electronic effects of substituents on
Co(III) porphyrins and their activity for the synthesis of
quinoxaline 3a was observed. Among the catalysts exam-
ined, Co(TpOMePP)Cl gave the best results. The results
are presented in Table 2.
The results of the quinoxaline synthesis by
Co(TpOMePP)Cl in various protic and aprotic solvents
are reported in Table 3. We found that these reactions
appeared to be largely dependent on the nature of the sol-
1
0
_
a
Isolated yield.
In order to find a suitable catalyst for the synthesis
of quinoxalines from 1,2-diamines and α-diketones, the
condensation reaction of benzene-1,2-diamine with ben-
zil in the presence of different metalloporphyrins were
chosen as a model to provide compound 3a (Scheme 1).
The reactions were studied in EtOH/H O (1:3 v/v) at
2
room temperature. The results are displayed in Table 1.
At first, this model reaction were carried out in the
presence of the catalytic amount of some metal com-
vent and the mixture of H O/EtOH (3:1 v/v) is the best
2
medium for these reactions (Table 3, entry 4).
To realize the generality and versatility of the catalyst,
different aryl and alkyl 1,2-diamines were condensed with
n+
n+
plexes of tetraphenylporphyrin [M TPPCl ] [M
=
n-2
3
+
3+
3+
3+
2+
2+
2+
2+
Cr , Mn , Fe , Co , Co , Ni , Cu , Zn and TPP =
tetraphenylporphyrin dianion] (10 mol %) to
examine the effects of the central metal on
the catalytic properties of porphyrin in these
reaction conditions (Fig. 1). The results are
summarized in Table 1. The yield of quinox-
aline is controlled by the variation of central
metal in porphyrin core. Trivalent metal-
R
R
R
N
M
N
N
N
R
3
+
3+
3+
3+
R =
H
M(TPP)
NH2
M(TpNH PP)
loporphyrins [Cr , Mn , Fe and Co ]
appear to give better yields of quinoxaline in
comparison with divalent metalloporphyrins
2
Me
OH
M(TpMePP)
M(TpOHPP)
NMe2
M(TpNMe2PP)
2
+
2+
2+
2+
[
Co , Ni , Cu and Zn ]. This reactivity
OSO Na M(TPPS4)
3
refers to this fact that, trivalent metallopor-
phyrins are more acceptor than divalent
metalloporphyrins. This behavior leads to
the increase interaction between metallopor-
phyrins, diketones and diamines.
NO2 M(TpNO PP)
CN
M(TpCNPP)
M(TpPyP)
2
Cl
M(TpClPP)
N
According to Table 1, entry 4, Co(TPP)Cl
is the most effective catalyst and the reac-
tion was completed in shorter reaction time.
NMe+
OMe M(TpOMePP)
M(TpMePyP)
Fig. 1. The structures of metalloporphyrins used in this study
Copyright © 2010 World Scientific Publishing Company
J. Porphyrins Phthalocyanines 2010; 14: 1053–1058

1054 K. ꢀOꢇAꢀꢀADI ꢀꢁ ꢂꢃ.
Table 2. Reaction of benzene-1,2-diamine (1.1mmol) with
benzil (1mmol) in the presence of various cobaltporphyrins
Table 3. The effect of various solvents (4 mL) on the reaction
of benzene-1,2-diamine (1.1 mmol) with benzil (1 mmol) in the
presence of Co(TpOMePP)Cl (0.1 mmol) at room temperature
(
0.1 mmol) as catalysts in EtOH/H O (1/3) (4 mL)
2
Entry
Cobalt(III) porphyrin
Time (min)
Yield (%)
Entry
Solvent
EtOH
Time (min)
Yield (%)
1
2
3
4
5
6
7
8
9
Co(TPP)Cl
90
50
75
70
60
70
70
80
65
60
70
60
70
65
1
2
3
4
5
6
7
8
9
10
120
120
40
45
60
75
80
50
45
45
45
50
50
Co(TpMePP)Cl
Co(TpOHPP)Cl
EtOH/H O (3/1)
2
300
50
EtOH/H O (1/1)
2
Co(TpNO PP)Cl
EtOH/H O (1/3)
35
2
2
Co(TpClPP)Cl
120
35
H O
2
120
120
120
120
120
120
Co(TpOMePP)Cl
CH CN
3
Co(TpNH PP)Cl
180
120
120
300
300
60
CHCl3
ethylacetate
DMF
2
Co(TpNMe PP)Cl
2
Co(TpPPS )Cl
4
1
1
1
0
1
2
Co(TpPyP)Cl
Co(TpMPyP)Cl
Co(TpCNPP)Cl
MeOH
Table 4. Synthesis of quinoxaline derivatives from 1,2-diamines and α-diketones
.
Entry
Diamine
Product
Time (min)
Yield (%)
81
mp [lit.][ref]
NH2
NH2
N
N
1
10
233-235
NH2
NH2
N
N
2
3
10
10
80
78
229-230 [230-232][19]
303-305 [304-306][19]
NH2
NH2
N
N
O N
2
NH2
NH2
O N
2
N
a
50
65
b
6
0
318-320 [319-320][19]
86-88 [81][26]
4
5
N
N
N
H
NH2
15
20
82
78
NH2
Ph
NH2
N
N
H
6
7
128-130 [124][27]
NH2
Ph
a
O N
2
NH2
NH2
O
2
N
N
N
H
41
60
30
208-210
b
6
3
Ph
N
N
NH2
NH2
8
80
129-130 [130-131][19]
(
Continued)
Copyright © 2010 World Scientific Publishing Company
J. Porphyrins Phthalocyanines 2010; 14: 1054–1058

APPꢁICAꢂIOꢃ Oꢄ ꢀꢅꢂAꢁꢁOPOꢆPꢇꢈꢆIꢃS AS ꢃꢅW CAꢂAꢁꢈSꢂS ꢄOꢆ ꢂꢇꢅ ꢅꢄꢄICIꢅꢃꢂ 1055
Table 4. (Continued)
.
Entry
Diamine
Product
Time (min)
25
Yield (%)
81
mp [lit.][ref]
NH2
NH2
N
N
9
115-117 [117-118][25]
NH2
NH2
N
N
1
1
0
1
40
60
78
175-177 [172][18]
O N
2
NH2
NH2
O N
2
N
N
a
46
193-194 [193-194][25]
b
6
0
OMe
OMe
NH2
NH2
a
1
1
1
2
3
N
N
60
60
43
148-150 [148-150][19]
128-130 [125-127][25]
b
59
OMe
NH2
a
4
6
5
N
N
NH2
b
2
OMe
OMe
NH2
NH2
a
6
0
41
118-120
166-167
N
N
4
5
b
5
7
OMe
NH2
N
N
1
1
60
75
NH2
NH2
N
N
6
7
120
25
72
78
157-159 [158][18]
180-183
NH2
Br
Br
N
N
NH2
1
NH2
a
b
at room temperature, at reflux conditions.
Copyright © 2010 World Scientific Publishing Company
J. Porphyrins Phthalocyanines 2010; 14: 1055–1058

1056 K. ꢀOꢇAꢀꢀADI ꢀꢁ ꢂꢃ.
O O
C C
Ph
Ph
NH2
NH2
H2O
+
N
N
Ph
C
Ph
Ph
Ph
C
CoIII
O
O+
CoIII
N
C
N
H2N+
NH2
Ph
Ph
Ph
Ph
C
C
C
OH2
CoIII
O
CoIII
HN
+NH2
Ph
N
NH
Ph
Ph
Ph
C
C
H2O
C
C
O
H2O +OH
CoIII
CoIII
+3
Scheme 2. A proposed mechanism for the condensation of benzene-1,2-diamine with benzil in the presence of Co porphyrin
some α-diketones. The results are summarized in Table 4.
As it is shown in Table 4, when aryl 1,2-diamines were
applied, all of the reactions proceeded efficiently and
the desired quinoxalines were obtained in excellent yields
and short reaction times. However, alkyl 1,2-diamines
afforded the corresponding quinoxaline derivatives
in slightly lower yields and longer reaction times. The
quinoxalines obtained from aryl 1,2-diamines are more
stable than the product from alkyl 1,2-diamine due to the
formation of conjugated system in the product. In addi-
tion, the structure of α-diketones did not significantly
affect on the results of the reaction.
Preparation of quinoxalines from 1,2-diamines and
α-diketones
To a mixture of α-diketone (1.1 mmol), metallopor-
phyrin (0.1 mmol) and EtOH/H O (1/3 (v/v), 4 mL) in
2
a 50 mL round-bottomed flask was added 1,2-diamine
(1.1 mmol), and the resulting mixture was stirred at room
temperature for the times reported in Table 4. After the
completion of the reaction, H O (10 mL) was added and
2
filtered. The product was dissolved in hot ethanol and
recrystallized to obtain the pure product. After the evapo-
ration of the solvent, the catalyst was washed with diethyl
ether (5 mL) and reused for another time without the loss
of the reactivity.
We proposed a mechanism to explain the catalytic
behavior of Co(III) porphyrin for the condensation reac-
tion of 1,2-diamines with 1,2-diketones (Scheme 2).
Selected spectral data
EXPERIMENTAL
Acenaphtho[1,2-b]quinoxaline. White solid; mp
1
2
33–235 °C. H NMR (CDCl ): d, ppm 7.80–7.83 (dd,
3
J13 = 1.75, J12 = 3.25, 2H, arom), 7.88–7.92 (t, J = 7.5,
H, arom), 8.15–8.18 (d, J = 4.25, 2H, arom), 8.26–8.29
General procedures
2
All chemicals were purchased from Merck or Fluka
chemical companies. All known compounds were identi-
(
3
1
dd, J = 1.75, J = 3.25, 2H, arom), 8.48–8.50 (d, J =
1
3
12
13
.25, 2H, arom). C NMR (CDCl ): d, ppm 122.3, 129.1,
3
1
fied by comparison of their melting points, H NMR and
29.6, 129.9, 130.0, 130.4, 132.3, 136.9, 141.7, 154.5.
1
3
C NMR data with the authentic samples.
Elemental anal. for C H N : calcd. (found): C, 85.02
1
8
10
2
(
85.11); H, 3.96 (3.92); N, 11.02 (11.08).
Preparation of porphyrins and metalloporphyrins
8
,9-dihydroacenaphtho[1,2-b]pirazine. White solid;
1
Porphyrins were prepared according to reported
methods [28–31]. Metalloporphyrins were obtained by
standard method [32].
mp 166–167 °C. H NMR (CDCl ): d, ppm 2.05 (s, 4H,
CH ), 7.3–7.78 (t, J = 7.5 Hz, 2H, arom), 7.98–8.0 (d, J =
3.5 Hz, 2H, arom), 8.01–8.04 (d, J = 4.2 Hz, 2H, arom).
3
2
Copyright © 2010 World Scientific Publishing Company
J. Porphyrins Phthalocyanines 2010; 14: 1056–1058

APPꢁICAꢂIOꢃ Oꢄ ꢀꢅꢂAꢁꢁOPOꢆPꢇꢈꢆIꢃS AS ꢃꢅW CAꢂAꢁꢈSꢂS ꢄOꢆ ꢂꢇꢅ ꢅꢄꢄICIꢅꢃꢂ 1057
Elemental anal. for C H N : calcd. (found): C, 81.53
1
4
10
2
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(
81.50); H, 4.89 (4.92); N, 13.58 (13.61).
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1
3
2
7
(
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3
s, 1H, arom). C NMR (CDCl ): d, ppm 128.0, 129.6,
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1
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3
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3
3
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1
3
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1
1
H, arom). C NMR (CDCl ): d, ppm 20.7, 20.8, 127.8,
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-
1
1
93–194 °C. IR (KBr): νmax, cm 1520, 1330, 760, 690.
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.0, 4H, arom), 7.46–7.49 (t, J = 7.0, 2H, arom), 7.59–
.62 (m, 4H, arom), 8.33–8.36 (d, J = 4.7 Hz, 4H, arom),
.56–8.59 (dd, J13 = 1.25, J12 = 4.75, 1H, arom), 9.12–
.13 (d, J = 1.2, 1H, arom).
1
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9
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8
9
3
6
-methyl-2,3-bis(4-bromophenyl)quinoxaline.
-
1
10. Firouzabadi H, Sardarian AR, Khayat Z, Karimi B
White solid; mp 180–183 °C. IR (KBr): νmax, cm 1040,
005, 820. H NMR (CDCl ): d, ppm 2.67 (s, 3H, CH ),
.43–7.44 (d, J = 3.75, 4H, arom), 7.53–7.54 (d, J = 3.75,
H, arom), 7.66–7.67 (d, J = 4.25, 1H, arom), 7.97 (s,
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2
1
14
2
2
H, 3.11 (3.08); Br, 35.19 (35.21); N, 6.17 (6.13).
,7-dimethyl-2,3-bis(4-methoxyphenyl)quinoxa-
6
1
13. Badran MM, Botros S, El-Gendy AA, Abdou NA,
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3
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24
22
2
2
calcd. (found): C, 77.81 (77.84); H, 5.99 (5.96); N, 7.56
7.64).
-nitro-2-phenylquinoxaline. White-yellow solid;
1
1
1
5. Sakurai T, Shi K, Sato H, Tashiro K, Osuka A, Saeki
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(
6
1
mp 208–210 °C. H NMR (CDCl ): d, ppm 7.64–7.67
m, 3H, arom), 8.30–8.34 (m, 3H, arom), 8.59 (dd, J =
3
1
30: 13812–13813.
(
12
6. Obata M, Matsuura N, Mitsuo K, Nagai H, Asai K,
Harada M, Hirohara S, Tanihara M and Yano S.
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9
9
1
.2, J13 = 2.4, 1H, arom), 9.06 (d, J = 2.4, 1H, arom),
.54 (s, 1H, olefin). FTIR: ν, cm 3000–3100 (νC-H),
520–1560 (νC=N, νC=C), 1340 (νN-O). Elemental anal. for
-
1
663–670.
C H N O : calcd. (found): C, 66.93 (66.84); H, 3.61
1
4
19
3
2
7. Hasaninejad A, Zare A, Mohammadizadeh MR and
(
3.67); N, 16.73 (16.59).
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