CoFe2O4 nanoparticles as a magnetically recoverable and reusable catalyst for the synthesis of arylaminotetrazoles and 5-aryloxytetrazoles

Article abstract of DOI:10.3184/174751914X13871210981307

An efficient and direct method is described for the synthesis of 5-arylamino-1H-tetrazoles (Isomer A) or 1-aryl-5-amino-1Htetrazoles (Isomer B) and 5-aryloxytetrazoles from arylcyanamides or cynates with nano CoFe ₂O₄ as a reusable a

Full text of DOI:10.3184/174751914X13871210981307

JOURNAL OF CHEMICAL RESEARCH 2014
FEBRUARY, 65–68
RESEARCH PAPER 65
CoFe2O4 nanoparticles as a magnetically recoverable and reusable catalyst
for the synthesis of arylaminotetrazoles and 5‑aryloxytetrazoles
Siavash Bahari* and Akbar Rezaei
Faculty of Science, Ahar Branch, Islamic Azad University, Ahar, Iran
An efficient and direct method is described for the synthesis of 5‑arylamino‑1H‑tetrazoles (Isomer A) or 1‑aryl‑5‑amino‑1H‑
tetrazoles (Isomer B) and 5‑aryloxytetrazoles from arylcyanamides or cynates with nano CoFe2O4 as a reusable and efficient
heterogeneous catalyst. Isomer A was obtained from arylcyanamides carrying electron‑withdrawing substituents on the aryl
ring, while isomer B was produced with electron‑releasing groups. The significant advantages of this methodology are high
yields, elimination of dangerous and harmful hydrazoic acid, simple work‑up procedure and the recovery and reusability of the
catalyst.
Keywords: arylaminotetrazole, aryloxytetrazole, cyanamides, cyanates, CoFe2O4 nanoparticles, heterogeneous catalyst
Tetrazoles have been employed as an isostere for the carboxylic
acid moiety,1 as ligands in coordination chemistry and as
explosives and rocket propellants.2,3 Tetrazole is a well-known
intermediate in the synthesis of imidoylazides.4
Ar
NH2
N
NH
N
N
or
HN
Ar
C
C
Ar
N
N
N
N
H
N
N
N
Nano CoFe2O4
DMF, 110 oC
+
NaN3
Classical methods for the synthesis of tetrazoles have
involved the reaction of azide ions with nitriles, cyanates
and cyanamides in the presence of acids or other catalysts in
organic solvents at high temperature and pressure.5–16 Among
the tetrazoles, arylaminotetrazoles and aryloxytetrazoles
have received attention because of their wide utility.4–16
However, the lack of convenient methods for the preparation
of arylaminotetrazoles restricts their potential application in
medicine. Generally, arylaminotetrazoles are synthesised by
the condensation reaction of cyanamides with hydrazoic acid,17
HOAc7 and FeCl3–SiO213 which lead to a mixture of products.
Earlier methods for the synthesis of arylaminotetrazoles or
5-aryloxytetrazoles suffer from drawbacks such as the use
of strong Lewis acids or expensive and toxic metals, drastic
reaction conditions, low yield, long reaction times, low
temperatures (–70 °C), tedious work-up procedures due to
the application of homogeneous catalyst and hydrazoic acid
formation. The latter is explosive and very toxic.18,19
Several regiospecific syntheses of arylaminotetrazoles have
been reported through the [2+3] cycloaddition of cyanamides
using NaN3 in the presence of catalysts such as ZnCl2,15 AlCl39
and Iranian Natrolite zeolite.14 Thus, the development of a
catalytic synthetic method for tetrazoles still remains an active
research area.
Therehasbeenaninterestinvariouschemicaltransformations
performed with heterogeneous catalysis20–24 and, in particular,
magnetic nanoparticles have emerged as a useful group.25–30
The separation of magnetic nanoparticles is simple, and an
attractive alternative to filtration or centrifugation as it prevents
the loss of catalyst and enhances reusability, making the catalyst
more cost-effective and promising for industrial applications.
Recently, magnetically separable CoFe2O4 nanoparticles, have
been prepared by a simple procedure and their catalytic activity
investigated.30
O
N
NH
N
Ar
Ar
O
N
Scheme 1 Synthesis of arylaminotetrazoles and 5‑aryloxytetrazoles using
magnetically separable CoFe2O4 nanoparticles.
Results and discussion
No reaction was observed when
a
mixture of
2,5-dichlorophenylcyanamide and sodium azide was
stirred for 5 h at 110 °C. However, addition of the nano
CoFe2O4 to the mixture has rapidly increased the yield of the
arylaminotetrazoles.
At the start, the reactivity of various catalysts were
investigated in the reaction of 2,5-dichlorophenylcyanamide
with sodium azide in different solvents (Table 1). FeCl3–SiO213
and glacial HOAc7 catalysts gave a mixture of isomers (A+B),
while nano CoFe2O4 gave just the isomer (A). Another method
needed 0.4 g of zinc (II) chloride as reagent under reflux in water
and involved long reaction times (15 h). ZnCl215 is a well-known
reagent, but it is sensitive to moisture and is difficult to recycle.
Natrolite zeolite14 is a local catalyst, but there are difficulties
in the preparation and availability of the catalyst. Zeolites
also have definite advantages and some disadvantages over
conventional solid catalysts in a certain number of applications.
The main limitations are (i) the great sensitivity of zeolites to
deactivation by irreversible adsorption or steric blockage by
high molecular weight by-products and (ii) the impossibility of
using their microporosity for the synthesis of bulky molecules.
Then, we optimised the amount of nano CoFe2O4 catalyst
required for the model reaction (Table 1). Water was not a
suitable solvent for this reaction. Sodium azide is insoluble
in most organic solvents, which has limited its application in
organic synthesis. However, cycloaddition reactions have been
carried out at high temperatures. DMF is a suitable solvent for
these cycloaddition reactions.13,14 The optimum amount of nano
CoFe2O4 was found to be 0.1 g in the presence of cyanamides
(2 mmol) and sodium azide (3 mmol) in DMF (6 mL). We next
examined a variety of structurally divergent phenylcyanamide
possessing a wide range of functional groups to understand
In continuation of our researches on the application of
heterogeneous catalyst,31 we report a new protocol for
preparation of arylaminotetrazoles and 5-aryloxytetrazoles
from cyanamides and cyanates, respectively using magnetically
separable CoFe2O4 nanoparticles as an efficient catalyst
(Scheme 1). This catalyst, can be prepared from inexpensive and
readily available materials and is environmentally acceptable
and recyclable.
* Correspondent. E-mail: siavashbahari89@gmail.com; s-bahari@iau-ahar.ac.ir
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66 JOURNAL OF CHEMICAL RESEARCH 2014
Table 1 Comparison of catalytic activities in the reaction of 2,5‑dichlorophenylcyanamide with sodium azide in different solvents
Entry
Catalyst
Solvent
DMFb
Time/min
120
30 h
15 h
9 h
95
105
105
105
Yield/%a
76
72
84
49
81
71
78
Product (A or B)
1
2
3
4
5
6
7
8
9
FeCl3‑SiO2 (0.1 g)
Glacial HOAc (3 mL)
ZnCl2 (0.4 g)
Natrolite zeolite (0.1 g)
Natrolite zeolite (0.1 g)
Nano CoFe2O4 (0.05 g)
Nano CoFe2O4 (0.07 g)
Nano CoFe2O4 (0.10 g)
Nano CoFe2O4 (0.10 g)
Nano CoFe2O4 (0.15 g)
A+B
A+B
A
A
A
A
A
A
A
Glacial HOAcc
H2Od
H2Od
DMFe
DMFb
DMFb
DMFb
87
87
87
DMSO
DMFb
105
105
10
A
aPure isolated products.
bReaction was carried out at 110 °C.
cRoom temperature.
dUnder reflux conditions.
eReaction was carried out at 110–115 °C.
Table 2 Preparation of 5‑arylamino‑1H‑tetrazoles (A) and 1‑aryl‑5‑amino‑1H‑tetrazoles (B) using nano CoFe2O4 from cyanamides at 110 °C
Entry
Substrate
Product (Isomer A or B)
4‑NO2C6H4NHTet (3b) (A)
2‑ClC6H4NHTet (3b) (A)
2,5‑(Cl)2C6H3NHTet (3c) (A)
4‑BrC6H4NHTet (3d) (A)
C6H5NHTet (3e) (A)
4‑MeC6H4NHTet (3f) (B)
2,4‑(Me)2C6H3NHTet (3g) (B)
2‑MeC6H4NHTet (3h) (B)
4‑NHTetC6H5NHTet (1i) (B)
4‑OMeC6H4NHTet (1j) (B)
2,6‑(Me)2C6H3NHTet (1k) (B)
Time/min
105
105
100
100
90
Yield/%a
84
86
87
86
85
86
85
85
88
86
87
M.p. (lit.)Ref.
1
2
3
4
5
6
7
8
9
4‑NO2C6H4NHCN (1a)
2‑ClC6H4NHCN (1b)
2,5‑(Cl)2C6H3NHCN (1c)
4‑BrC6H4NHCN (1d)
C6H5NHCN (1e)
4‑MeC6H4NHCN (1f)
2,4‑(Me)2C6H3NHCN (1g)
2‑MeC6H4NHCN (1h)
4‑NHCNC6H5NHCN (1i)
4‑OMeC6H4NHCN (1j)
2,6‑(Me)2C6H3NHCN (1k)
218–220 (218–220)11
228–230 (228–230)11
272–274 (272–274)11
249–250 (249–250)11
215–217 (215–217)11
178–179 (178–179)11
199–201 (199–201)11
191–192 (191–192)11
264–266 (264–266)11
211–213 (211–213)11
211–213 (–)
55
55
55
50
55
55
10
11
aPure isolated product.
the scope and generality of the nano CoFe2O4-promoted [2+3]
cycloaddition reaction to form arylaminotetrazoles. These
results are summarised in Table 2.
Table 2). It was reported that the 1-(4-nitrophenyl)-5-amino-
1H-tetrazole (isomer B) was obtained using hydrazoic acid and
a mixture of isomers (A+B) were obtained by the use of FeCl3–
SiO2 or glacial HOAc, while with nano CoFe2O4 only a single
5-(4-nitrophenyl)amino-1H-tetrazole (isomer A) was produced.
In the presence of two CN groups, 1i (Table 2, entry 9) afforded
the double-addition product. 2,6-Dimethylphenylcyanamide
and 2-methylphenylcyanamide (Table 2, entry 11 and 8)
interestingly gave B isomer, while with HOAc and FeCl3–SiO2,
the A isomer and the mixture of isomers (A+B) were obtained.
The nano CoFe2O4 probably has an important role in the
promotion of the synthesis of arylaminotetrazoles as a Lewis
acid. A plausible mechanism is shown in Scheme 2. Nano
CoFe2O4 may show complexation towards nitrile group of
cyanamides and thus may enhance its electrophic character.
It involves activation of the nitrile group over surface of the
As shown in Table 2, cyanamides having electron releasing
groups on the rings (entries 6–8, 10, 11) were completed at
110 °C after 55 min, while the species bearing the electron
withdrawing species (entries 1–4) required longer reaction
times. The influences of various substituents in different ortho,
metaorparapositionsonthetypeoftheproductswereexamined.
Substituents on the aromatic ring of cyanamide had an important
effect on the type of product (isomers A or B) and these results
were incorporated in Table 2. In the case of cyanamides having
the electron releasing groups, 1-aryl-5-amino-1H-tetrazoles
(B) was obtained (entries 6–8, 10 and 11, Table 2). When the
substituent was replaced by an electron-withdrawing group,
the 5-arylamino-1H-tetrazoles (A) were obtained (entries 1–4,
Cat
N
C
N
N
N
N
N NH
3a-e
A Isomer
N
Nano Cat
DMF
H
H
+
C
Ar
Ar
Ar
N
N
N
N
N
H
N
NH
H
Ar
1a-k
2
N
N
NH2
N
3f-k
B Isomer
N
Ar
C
Cat
N
N
N
N
N
H
Scheme 2 Mechanism of nano CoFe2O4 catalysed synthesis of arylaminotetrazoles.
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JOURNAL OF CHEMICAL RESEARCH 2014 67
Table 3 Preparation of 5‑aryloxytetrazoles using nano CoFe2O4 from cyanates at 110°C
Entry
Substrate
C6H5OCN (1l)
4‑OMeC6H4OCN (1m)
2,6‑(Me)2C6H3OCN (1n)
4‑ClC6H4OCN (1o)
Product
C6H5OTet (3l)
4‑OMeC6H4OTet (3m)
2,6‑(Me)2C6H3OTet (3n)
4‑ClC6H4OTet (3o)
Time/min
200
180
180
220
Yield/%a
81
80
78
79
82
81
M.p. (lit.)Ref.
1
2
3
4
5
6
136–138 (137–138)33
150–151 (149–150)33
171–173 (173–174)33
166–168 (166–167)33
139–140 (140–142)33
161–163 (162–163)33
4‑MeC6H4OCN (1p)
4‑NO2C6H4OCN (1q)
4‑MeC6H4OTet (3p)
4‑NO2C6H4OTet (3q)
180
220
aPure isolated product.
nano CoFe2O4 and subsequent nucleophilic attack of the sodium
azide. A similar mechanism has been reported for the synthesis
of arylaminotetrazoles using catalyst ZAS.13
recoverable from the reaction mixture by applying external
magnetic field and reused four times without significant loss of
catalytic activity. This methodology may find widespread use
in organic synthesis for the preparation of tetrazoles.
The reactivity of several cyanates was also tested in the
reaction with sodium azide in the presence of nano CoFe2O4
under thermal conditions. The results are given in Table 3. The
electronic nature or position of the substituents on the aromatic
ring of cyanates affected the reaction time. As shown in Table 3,
cyanates having the methyl as electron-releasing groups (entries
2,3 and 5) were completed at 110 °C after 180 min, while the
species bearing the –NO2 or –Cl electron-withdrawing groups
(entries 4 and 6) required longer reaction times.
Experimental
All the solvents and reagents were purchased at the highest commercial
quality and used without further purification. All reaction mixtures
were stirred magnetically and were monitored by TLC using 0.25 mm
E-Merck silica gel 60 F254 pre-coated glass plates, which were
visualised with UV light and then developed by using iodine mixed
with silica gel 60–120 mesh. Melting points were recorded on a Buchi
R-535 apparatus and are uncorrected. IR spectra were recorded on a
The structure of the products was confirmed by IR, 1H NMR
and 13C NMR spectral data and melting points. 5-Arylamino-
1H-tetrazoles isomers (A) contain two NH bonds [NH of the
amine attached to the aryl group (NHA) and NH of the tetrazole
ring (NHT)] and 1-aryl-5-amino-1H-tetrazoles isomers (B)
contain a NH2 bond. In the IR spectra of the tetrazoles, the CN
peak had disappeared and one absorptions band (NH stretching
band) was detected. The appearance of a signal about δ= 154–
157 ppm for the tetrazole ring carbon in the 13C NMR spectra
was evidence for the formation of tetrazoles.9,14,15
The reusability of the catalyst (Table 3) was examined
with 4-nitrophenylcyanamide and NaN3 under the optimised
reaction conditions. CoFe2O4 nanoparticles are recyclable
without loss of significant catalytic activity. The catalyst was
separated by an external magnet and reused for subsequent
experiments under similar reaction conditions. Yields of the
product decreased only slightly after four cycles (Table 4).
This reusability demonstrated the high stability and turnover
of CoFe2O4 magnetic nano catalyst under operating conditions.
Work is in progress to develop novel magnetically recoverable
and reusable catalysts and study their application in the other
type of reactions.
1
Perkin-Elmer FT-IR 240-C spectrophotometer using KBr optics. H
NMR and 13C NMR spectra were recorded on Bruker Avance 400 MHz
spectrometers in CDCl3 and DMSO using TMS as internal standard,
with chemical shifts being given in ppm with respect to internal TMS
and J values quoted in Hz.
Preparation of the catalyst
Two aqueous solutions of FeCl3 (1.5 g, 9.3 mmol, 50 mL) and
CoCl2·6H2O (1 g, 4.2 mmol, 50 mL) were mixed in a 200 mL flat
bottom flask and placed in an ultrasonic bath. An aqueous KOH
solution (3 M, 25 mL) was added dropwise under argon atmosphere
with continuous ultrasonic irradiation (frequency 40 KHz and power of
40 KW). Prior to mixing, all three solutions were sonicated for 30 min
to remove dissolved oxygen. The temperature of the sonicator bath was
raised to 60 °C and the mixture was further sonicated for 30 min in air.
A black precipitate was formed during this time. The reaction mixture
was centrifuged (14,000 rpm) at ambient temperature for 15 min.
The mixture was subjected to successive sonication (30 min) and
centrifugation (15 min) for five times. The black precipitate was then
separated, washed with copious amounts of distilled water, ethanol and
kept overnight in an incubator at 60 °C for ageing. The precipitate was
then dried in an oven at 100 °C for 1 h and subsequently kept under high
vacuum (10–2 bar) for 1 h. Finally, the black particles were suspended
in dry ethanol (50 mL) and subjected to successive sonication (30 min)
and centrifugation (15 min) repeatedly until a brown coloured solution
appeared. The precipitate was separated, dried and stored for further
applications.30
Table 4 Reusability of the CoFe2O4 catalyst
Entry
Yield/%
Recovery of CoFe2O4/%
Refresh
84
83
83
81
80
99
99
98
98
97
1
2
3
4
Preparation of the arylcyanamides
The arylcyanamides were prepared according to the literature.13,32
Preparation of the arylcyanates
The arylcyanates were prepared according to the literature.33
Synthesis of arylaminotetrazoles and 5‑aryloxytetrazoles; general
procedure
Conclusion
In conclusion, we have developed a novel and highly efficient
method for the synthesis of various arylaminotetrazoles and
5-aryloxytetrazoles by treatment of cyanamides or cyanates
with sodium azide in the presence of CoFe2O4 as a magnetically
recoverable and reusable catalyst. The significant advantages of
this methodology are the high yields, elimination of dangerous
and harmful hydrazoic acid and simple work-up procedure.
The catalyst is easily prepared, stable to air and magnetically
A mixture of arylcyanamides (1a–k) or arylcyanates (1l–q) (2 mmol),
sodium azide (3 mmol), nano CoFe2O4 (0.1 g) and DMF (6 mL) was
placed in a round-bottomed flask and stirred for the appropriate time
(Table 2) at 110 °C. The progress of the reaction was monitored by
TLC. After completion of the reaction, the catalyst was separated by an
external magnet, washed with ethyl acetate and activated at 100 °C for
2 h. Then, the resultant mixture was treated with ethyl acetate (35 mL)
and 5 N HCl (20 mL). The organic layer was separated and the aqueous
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68 JOURNAL OF CHEMICAL RESEARCH 2014
5
6
7
A.R. Modarresi-Alam and M. Nasrollahzadeh, Turk. J. Chem., 2009, 33,
267.
M. Nasrollahzadeh, Y. Bayat and D. Habibi, S. Moshaee, Tetrahedron
Lett., 2009, 50, 4435.
D. Habibi, M. Nasrollahzadeh and Y. Bayat, Synth. Commun., 2011, 41,
2135.
D. Habibi and M. Nasrollahzadeh, Synth. Commun., 2012, 42, 2023.
D. Habibi and M. Nasrollahzadeh, Synth. Commun., 2010, 40, 3159.
layer was extracted with ethyl acetate (20 mL) again. The combined
organic layers were concentrated under reduced pressure. The crude
solid was recrystallised with aqueous ethanol to afford the pure
product in high yields. All products were characterised by spectral
analysis. All compounds were compared with the corresponding
compounds prepared by the reported procedure.4,9,14,15
8
9
1‑(2,6‑Dimethylphenyl)‑5‑amino‑1H‑tetrazole (3k, Table 2, entry
11): M.p. 147–149 °C; IR (KBr, cm–1): 3430, 3295, 3070, 2955, 2915,
2850, 1650, 1601, 1586, 1538, 1474, 1440, 1376, 1349, 1260, 1217, 1160,
10 M. Nasrollahzadeh, D. Habibi, Z. Shahkarami and Y. Bayat, Tetrahedron,
2009, 66, 3866.
11 D. Habibi, M. Nasrollahzadeh, A.R. Faraji and Y. Bayat, Tetrahedron,
2010, 66, 3866.
12 D. Habibi, M. Nasrollahzadeh, H. Sahebekhtiari and S.M. Sajadi, Synlett,
2012, 23, 2795.
13 D. Habibi and M. Nasrollahzadeh, Monatsh. Chem., 2012, 143, 925.
14 D. Habibi, M. Nasrollahzadeh, L. Mehrabi and S. Mostafaee, Monatsh.
Chem., 2013, 144, 725.
15 D. Habibi, H. Nabavi and M. Nasrollahzadeh, J. Chem., 2013, Article ID
645313.
16 D. Habibi, M. Nasrollahzadeh and T.A. Kamali, Green Chem., 2011, 13,
3499.
17 W.L. Garbrecht and R.M. Herbst, J. Org. Chem., 1953, 18, 1014.
18 M.S. Congreve, Synlett, 1996, 359.
19 R.A. Henry, W.G. Finnegan and E. Lieber, J. Am. Chem. Soc., 1954, 76, 88.
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and A. Mohajeri, Turk. J. Chem., 2010, 34, 613.
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22 D. Habibi, M. Nasrollahzadeh and H. Sahebekhtiari, J. Mol. Catal. A:
Chem., 2013, 378, 148.
23 A.R. Modarresi-Alam, M. Nasrollahzadeh and F. Khamooshi, Arkivoc,
2007, 16, 238.
24 A.R. Modarresi-Alam, F. Khamooshi, M. Nasrollahzadeh and H.A.
Amirazizi, Tetrahedron, 2007, 63, 8723.
1
1114, 917, 869, 760, 700, 662, 636, 546, 516, 496; H NMR (500 MHz,
DMSO-d6): δH 2.25 (s, 6H), 5.24 (s, 2H), 7.03 (s, 3H); 13C NMR
(125 MHz, DMSO-d6): δC 157.5, 137.1, 136.6, 128.3, 126.3, 18.6; Anal.
calcd for C9H11N5: C, 57.12; H, 5.86; N, 37.02; found: C, 57.18; H, 5.90; N,
37.09%.
5‑(Phenoxy)tetrazole (3l, Table 3, entry 1): 1H NMR (500 MHz,
DMSO-d6), δH 7.25 (s, 5H), 12.10 (s, br, 1H).
5‑(4‑Methoxyphenoxy)tetrazole (3m, Table 3, entry 2): 1H NMR
(500 MHz, DMSO-d6), δH 3.91 (s, 3H), 7.11 (d, J=10.2 Hz, 2H), 7.51 (d,
J=10.2 Hz, 2H), 8.49 (s, 1H).
1
5‑(2,6‑Dimethylphenoxy)tetrazole (3n, Table 3, entry 3): H NMR
(500 MHz, DMSO-d6), δH 2.42 (s, 3H), 7.34 (s, 4H), 9.90 (s, 1H).
5‑(4‑Chlorophenoxy)tetrazole (3o, Table 3, entry 4): 1H NMR
(500 MHz, DMSO-d6), δH 7.40 (s, 4H), 8.71 (s, br, 1H).
5‑(4‑Methylphenoxy)tetrazole (3p, Table 3, entry 5): 1H NMR
(500 MHz, DMSO-d6), δH 2.30 (s, 6H), 7.18 (s, 3H), 10.40 (s, 1H).
5‑(4‑Nitrophenoxy)tetrazole (3q, Table 3, entry 6): 1H NMR
(500 MHz, DMSO-d6), δH 7.61 (d, J=8.7 Hz, 2H), 8.39 (d, J=8.7 Hz, 2H),
13.01 (s, br, 1H).
We thank the Islamic Azad University, Ahar Branch, for partial
support of this research.
25 M. Nasrollahzadeh, A. Ehsani and A. Rostami-Vartouni, Ultrason.
Sonochem., 2014, 21, 275.
26 A.R. Modarresi-Alam, M. Nasrollahzadeh and F. Khamooshi, Scient.
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Int. Mater. Rev., 2004, 49, 125.
28 Y.S. Kang, S. Risbud, J.F. Rabolt and P. Stroeve, Chem. Mater., 1996, 8,
2209.
Received 25 October 2013; accepted 25 November 2013
Paper 1302251 doi: 10.3184/174751914X13871210981307
Published online: 5 February 2014
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