Capture of 3-amino-4-oxycyanofurazan and characterization of isoxazole product

Article abstract of DOI:10.1002/jhet.842

1,3-Dipolar cycloaddition reaction between nitrile oxide and alkyne was used to capture 3-amino-4-oxycyanofurazan (AOCF), which was considered as the key intermediate during the synthesis of 3,4-bis(4-aminofurazano-3-yl)furoxan (DATF) from 3-amino-4-chloroximinofurazan. The isolated isoxazoles from the reaction afforded evidences for the existence of AOCF. The structures of the isoxazoles were characterized by IR, ¹H NMR, ¹³C NMR, MS, and elemental analysis. In addition, single crystal X-ray diffraction of one isoxazole was obtained.

Full text of DOI:10.1002/jhet.842

Month 2013
Capture of 3‐Amino‐4‐oxycyanofurazan and Characterization of
Isoxazole Product
Yifen Luo, Bozhou Wang, Guofang Zhang, Yanshui Zhou,
and Peng Liana
a
a
b
a
*
aXi’an Modern Chemistry Research Institute, Xi’an 710065, People’s Republic of China
bShaanxi Normal University, Xi’an 710062, People’s Republic of China
*
E-mail: luoyiluoyiluoyi204@163.com
Received August 25, 2010
DOI 10.1002/jhet.842
Published online 00 Month 2013 in Wiley Online Library (wileyonlinelibrary.com).
1,3‐Dipolar cycloaddition reaction between nitrile oxide and alkyne was used to capture 3‐amino‐4‐
oxycyanofurazan (AOCF), which was considered as the key intermediate during the synthesis of 3,4‐bis
(4‐aminofurazano‐3‐yl)furoxan (DATF) from 3‐amino‐4‐chloroximinofurazan. The isolated isoxazoles
from the reaction afforded evidences for the existence of AOCF. The structures of the isoxazoles were
1
characterized by IR, H NMR, 13C NMR, MS, and elemental analysis. In addition, single crystal X‐ray
diffraction of one isoxazole was obtained.
J. Heterocyclic Chem., 00, 00 (2013).
INTRODUCTION
RESULTS AND DISCUSSION
Furoxan was considered as an excellent structure for
constructing high energetic density materials (HEDMs),
as it could increase crystal density and improve explosive
performance [1–3]. Because of this, the introduction of
one or more structures of furoxan to an explosive molecule
has been actively researched by a great number of
researchers in recent years [4,6]. Some derivatives of
furoxan also could be used as high-density explosives.
3,4‐Bis(4‐aminofurazano‐3‐yl)furoxan (DATF) was among
the most promising HEDM candidates derivated from
furoxan for its excellent properties [7, 8].
To prove the existence of an unstable intermediate, it
was good idea to capture and/or convert it to a stable
compound before it decomposed. If the stable compound
could be isolated and identified, the existence of the
unstable intermediate can be proved.
As to AOCF, alkynes were applied to capture it, because
they could form stable isoxazoles through 1,3‐dipolar
cycloaddition reaction [19, 20], which have been extensively
studied experimentally and theoretically (Scheme 3). This
reaction was chosen because of its high yield, stereoselection,
and mild condition.
DATF could be obtained from propanedinitrile
according to the reported procedure [9, 10] shown in
Scheme 1. Unfortunately, the procedure suffered from
low yield of the last step. A clear mechanism of this
reaction might provide idea for some scholars to
improve the yield as well as understand the microcos-
mic reactive process more clearly. To our knowledge,
only a primitive mechanism was reported, which
proposed an intermediate, 3‐amino‐4‐oxycyanofurazan
(AOCF) [11, 12], presenting before the formation of
DATF (Scheme 2). However, the mechanism was
unproved, because AOCF was unstable even at low
temperature and could not be isolated from the reaction
system [13–18].
It should be noted that the dimerization of AOCF
leading to DATF was a “side reaction” at this moment
and must be avoided, so the capturing was carried out
under neutral condition. Under this condition, the hydrogen
chloride elimination of 3‐amino‐4‐chloroximinofurazan was
slow and the concentration of nitrile oxide was low, so the
dimerization of nitrile oxide was prohibited. At the same
time, because of the electron‐withdrawing character of
nitrile oxide and high concentration of alkynes, 1,3‐dipolar
cycloaddition reaction was the dominant reaction, and
also all of the nitrile oxide generated in situ was converted
to isoxazoles.
Hexabutylditin (Bu3SnSnBu3) was used as initiator, as
it works well under this condition. This reaction may be
initiated by homolytic cleavage of hexabutylditin and
formed tributyltin radical. The radical would deprive the
chlorine atom of hydroximic chloride, and AOCF was
Here, we report a method that can prove the existence of
AOCF in the reaction by capturing it in situ and thereof
prove the mechanism.
© 2013 HeteroCorporation

Y. Luo, B. Wang, G. Zhang, Y. Zhou, and P. Lian
Vol 000
Table 1
Scheme 1
Atomic coordinates (×104) and equivalent isotropic displacement
parameters (nm2 × 103)α.
Atoms
x
y
z
U(eq)α
Cl(1)
N(1)
N(2)
N(3)
N(4)
O(1)
O(2)
C(1)
C(2)
C(3)
C(4)
C(5)
C(6)
11 (1)
2459 (1)
1934 (1)
1207 (1)
1755 (1)
1427 (1)
1490 (1)
2013 (1)
1551 (1)
1421 (1)
945 (1)
11322 (1)
10369 (4)
7137 (4)
5398 (5)
10116 (4)
5245 (4)
10459 (3)
8409 (4)
7286 (5)
8092 (4)
7036 (5)
8596 (4)
8760 (5)
1067 (1)
6260 (1)
6631 (1)
5122 (1)
4106 (1)
6073 (1)
3120 (1)
6016 (2)
5071 (1)
4143 (1)
3214 (2)
2611 (2)
1545 (2)
63 (1)
64 (1)
60 (1)
69 (1)
57 (1)
77 (1)
60 (1)
45 (1)
45 (1)
44 (1)
48 (1)
47 (1)
55 (1)
Scheme 2
1005 (1)
645 (1)
Figure 1 showed the molecular structure of 4, which
was consisted of a chloromethyl group and an amino
furazano structure. It could be seen from Tables 2–4 that
bond lengths, angles, and dihedral angels of 4 were in
the normal range [21]. The chloromethyl group was
connected by C5 to the isoxazone ring. Therefore, in
the reaction system, the product was unique and had no
isomeric compound.
Scheme 3
CONCLUSIONS
AOCF, an unstable intermediate for the synthesis of
DATF from 3‐amino‐4‐chloroximino furazan was captured
in situ by alkynes and converted to isoxazoles through
1,3‐dipolar cycloaddition reaction. The corresponding
isoxazoles were obtained with high yield and purity. In
obtained. It should be mentioned that DATF could be isolated
from the reaction mixture, if one of the alkynes was absent.
Five alkynes were applied to capture AOCF, and five
isoxazoles were obtained with high yield. The structures of
the isoxazoles were confirmed by some analytic data. The
general synthetic process was shown as follows (Scheme 4).
Single crystals of 4 were cultured by slow evaporation of
its ethanol solution. The X‐ray single crystal structure of 4
was determined. The nonhydrogen coordinates and thermal
parameters were listed in Table 1. The bond lengths were
summarized in Table 2. The bond angles were summarized
in Table 3. The dihedral angels were summarized in Table
4. The molecular structure and 3D packing of 4 were
shown in Figures 1 and 2, respectively.
addition, their structures were confirmed by IR, 1H NMR, 13
C
NMR, MS, elemental analysis, and single crystal X‐ray
diffraction. These results proved the proposed mechanism.
EXPERIMENTAL
IR spectrum was recorded using a Nicolet Model NEXUS 870
FTIR instrument and a model DTGS detector. KBr pellet
samples, well mixed by about 0.7 mg of sample and 150 mg
1
of KBr, were used. The H NMR and 13C NMR spectra were
performed on a Bruker AV 500 MHz superconducting NMR
spectrometer (Bruke Biospin International AG, Switzerland).
DMSO‐d6 was the solvent, and tetramethyl silane was an internal
standard. Elemental analyses of carbon, hydrogen, and nitrogen
were carried out with an Elementary Vario EL‐III microanalyzer.
Differential scanning calorimetry (DSC) measurements were
carried out on the TA instruments, Model DSC 910S under
static atmosphere of N2 at the pressure of 0.1 and 1 MPa with
heating rate of 10°C min−1. Samples weighting from 0.5 to 1.0 mg,
loaded in an aluminum sample cell, were used. 3‐Amino‐4‐
chloroximinofurazan was prepared in our laboratory [7], and
other reagents were available commercially.
Scheme 4
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet.842

Month 2013
Capture of 3‐Amino‐4‐oxycyanofurazan and Characterization of Isoxazole Product
Table 2
Selected bond lengths (nm × 10−1) for compound 4 crystal structure parameters.
Bonds
Exp
Bonds
Exp
Bond
Exp
Cl(1)─C(6)
N(1)─C(1)
N(1)─H(1A)
N(1)─H(1B)
N(2)─C(1)
N(2)─O(1)
N(3)─C(2)
1.794 (2)
1.333 (3)
0.8600
N(3)─O(1)
N(4)─C(3)
N(4)─O(2)
O(2)─C(5)
C(1)─C(2)
C(2)─C(3)
C(3)─C(4)
1.366 (2)
1.307 (3)
1.402 (2)
1.349 (3)
1.433 (3)
1.456 (3)
1.410 (3)
C(4)─C(5)
C(4)─H(4)
C(5)─C(6)
C(6)─H(6A)
C(6)─H(6B)
1.340 (3)
0.9300
1.480 (3)
0.9700
0.8600
1.312 (3)
1.398 (3)
1.287 (3)
0.9700
Table 3
Selected bond angles (in °) for compound 4 crystal structure parameters.
Bond angles
Exp
Bond
Exp
Bond
Exp
C(1)─N(1)─H(1A)
C(1)─N(1)─H(1B)
H(1A)─N(1)─H(1B)
C(1)─N(2)─O(1)
C(2)─N(3)─O(1)
C(3)─N(4)─O(2)
N(3)─O(1)─N(2)
C(5)─O(2)─N(4)
N(2)─C(1)─N(1)
N(2)─C(1)─C(2)
120.0
120.0
120.0
105.10 (18)
106.26 (18)
105.20 (16)
110.82 (16)
108.52 (15)
124.3 (2)
108.2 (2)
N(1)─C(1)─C(2)
N(3)─C(2)─C(1)
N(3)─C(2)─C(3)
C(1)─C(2)─C(3)
N(4)─C(3)─C(4)
N(4)─C(3)─C(2)
C(4)─C(3)─C(2)
C(5)─C(4)─C(3)
C(5)─C(4)─H(4)
C(3)─C(4)─H(4)
127.54 (19)
109.66 (19)
120.9 (2)
129.4 (2)
111.93 (19)
119.54 (19)
128.5 (2)
104.4 (2)
127.8
C(4)─C(5)─O(2)
C(4)─C(5)─C(6)
O(2)─C(5)─C(6)
C(5)─C(6)─Cl(1)
C(5)─C(6)─H(6A)
Cl(1)─C(6)─H(6A)
C(5)─C(6)─H(6B)
Cl(1)─C(6)─H(6B)
H(6A)─C(6)─H(6B)
109.94 (18)
134.2 (2)
115.83 (19)
110.35 (16)
109.6
109.6
109.6
109.6
108.1
127.8
Table 4
Selected dihedral angles (in deg) for compound 4 crystal structure parameters.
Dihedral angles
Exp
Bond
Exp
Bond
Exp
C(2)─N(3)─O(1)─N(2)
C(1)─N(2)─O(1)─N(3)
C(3)─N(4)─O(2)─C(5)
O(1)─N(2)─C(1)─N(1)
O(1)─N(2)─C(1)─C(2)
O(1)─N(3)─C(2)─C(1)
O(1)─N(3)─C(2)─C(3)
N(2)─C(1)─C(2)─N(3)
N(1)─C(1)─C(2)─N(3)
−0.2 (3)
0.2 (3)
0.0 (2)
−179.1 (2)
−0.1 (2)
0.1 (3)
−176.8 (2)
0.0 (3)
N(2)─C(1)─C(2)─C(3)
N(1)─C(1)─C(2)─C(3)
O(2)─N(4)─C(3)─C(4)
O(2)─N(4)─C(3)─C(2)
N(3)─C(2)─C(3)─N(4)
C(1)─C(2)─C(3)─N(4)
N(3)─C(2)─C(3)─C(4)
C(1)─C(2)─C(3)─C(4)
N(4)─C(3)─C(4)─C(5)
176.5 (2)
−4.5 (4)
C(2)─C(3)─C(4)─C(5)
C(3)─C(4)─C(5)─O(2)
C(3)─C(4)─C(5)─C(6)
N(4)─O(2)─C(5)─C(4)
N(4)─O(2)─C(5)─C(6)
C(4)─C(5)─C(6)─Cl(1)
O(2)─C(5)─C(6)─Cl(1)
176.2 (2)
1.1 (2)
−176.0 (2)
−0.7 (2)
176.96 (19)
93.4 (3)
−83.6 (2)
0.7 (3)
−176.88 (19)
176.4 (2)
0.2 (4)
−0.8 (4)
−177.0 (2)
−1.2 (3)
179.0 (2)
General procedure for DATF. To 600‐mL diethyl ether
solution of 3‐amino‐4‐chloroximinofurazan (48 g, 0.295 mol) in
a three‐necked, round‐bottomed flask fitted with a mechanical
stirrer and a dropping funnel, 490‐mL 3% aqueous solution of
sodium carbonate was added dropwise at 0∼3°C (Scheme 5).
After the reaction, the temperature was maintained at 2∼10°C
for 3 h [7]. The solution was evaporated to dryness under
reduced pressure, and the residue was recrystallized from
ethanol and afforded the product 27.5 g with a yield of 73.6%.
1H NMR (DMSO‐d6, 500 MHz) δ, ppm: 6.61(s, 4H, NH2); 13
C
NMR (DMSO‐d6, 125 MHz) δ, ppm: 156.4, 155.5, 133.7, 136.6,
104.6, 147.0; IR (KBr) υ: 3459, 3332(NH2), 1635,1559, 1046,
1414, 1401, 1361 (furazan), 1609, 1533, 1463, 991(furoxan)
cm−1; Anal. calcd for C6N8H4O4: C 28.58, H 1.60, N 44.44;
Found C 28.63, H 1.31, N 44.46.
Figure 1. Molecular structure for compound 4.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet.842

Y. Luo, B. Wang, G. Zhang, Y. Zhou, and P. Lian
Vol 000
(s, 9H, 3CH3); 13C NMR (DMSO‐d6, 125 MHz) δ, ppm:
182.260, 154.941, 151.791, 138.631, 98.198, 32.557, 28.393;
IR (KBr) υ: 3464, 3343 (NH2), 2968∼2871(CH3), 1632,1553
(furazan) cm−1; Anal. calcd for C7H8N4O4: C 51.92, H 5.769,
N 26.92; found C 51.74, H 5.802, N 26.83; MS (EI) m/z(%):
208 (M+, 40), 151(100), 135(80),109(75), 95(45),43(82).
3‐(4‐Aminofurazan‐3‐yl)‐5‐brommethylisoxazone (3). Yield:
0.44 g (73.0%) m.p.147.28°C (DSC, 10°C min−1); 1H NMR
(DMSO‐d6, 500 MHz) δ, ppm: 7.197(s, H, CH), 6.431(s, 2H,
NH2), 4.949(s, 2H, CH2); 13C NMR(DMSO‐d6, 125 MHz) δ,
ppm: 169.563, 154.937, 152.370, 138.291, 103.087, 19.056;
IR (KBr) υ: 3453, 3325(NH2), 1634,1558(furazan), 733(Cl)
cm−1; Anal. calcd for C6H5N4O2Br: C 29.39, H 2.041, N
22.85; found C 29.54, H 2.235, N 22.81; MS (EI) m/z(%): 244
(M+,27), 246((M+2)+, 27), 187(38), 165(10), 108(83), 68
(100), 53(39),42(15).
3‐(4‐Aminofurazan‐3‐yl)‐5‐chloromethyl‐isoxazone (4).
Yield: 0.33 g (66.9%). m.p.122.72°C (DSC, 10°C min−1);
1H NMR (DMSO‐d6, 500 MHz) δ, ppm: 7.203(s, H, CH),
6.434(s, 2H, NH2), 5.083(s, 2H, CH2); 13C NMR(DMSO‐d6, 125
MHz) δ, ppm: 169.304, 154.963, 152.301, 138.297, 103.286,
33.844; IR (KBr) υ: 3459,3334(NH2), 3259∼3160(CH2),
1634,1558(furazan), 734(Cl) cm−1; Anal. calcd for C6H5N4O2Cl :
C 35.91, H 2.494, N 27.93; found C 35.98, H 2.556, N 27.69; MS
(EI) m/z(%): 200(M+,46), 202((M+2)+, 15), 143(100), 107(17), 68
(76), 58(45),49(28).
Figure 2. Packing of compound 4 molecules in the crystal.
3‐(4‐Aminofurazan‐ 3‐yl)‐5‐hydroxymethyl‐isoxazone (5).
Yield: 0.29 g (64.8%). m.p.171.22°C (DSC, 10°C min−1);
1H NMR (DMSO‐d6, 500 MHz) δ, ppm: 6.950(s, H, CH),
6.412(s, 2H, NH2), 5.826(t, J = 6.0 Hz, 1H, OH), 4.690(d,
J = 6.0 Hz, 2H, CH2); 13C NMR(DMSO‐d6, 125 MHz) δ,
ppm:174.673, 155.008, 151.859, 138.592, 100.772, 54.613;
IR (KBr) υ: 3472, 3359(NH2), 3131(OH), 2948∼2884
(CH2), 1633,1558(furazan) cm−1; Anal. calcd for C6H6N4O3
: C 39.56, H 3.297, N 30.77; found C 39.76, H 3.450, N
30.47; MS (EI) m/z(%): 182 (M+, 40), 125(100), 68(75), 53
(28),40(15).
Scheme 5
General procedure for the five isoxazones. 3‐Amino‐4‐
chloroximinofurazan (0.4 g, 2.46 mmol) in 30‐mL diethyl ether
was transferred into a three‐necked, round‐bottomed flask fitted
with a mechanical stirrer and a dropping funnel. Hexabutylditin
(1.4 g, 2.46 mmol) and an alkyne (1.2 mmol) were then added.
The reaction mixture was irradiated with a General Electric
sunlamp for 12 h. The reaction temperature was maintained at 25°
C by keeping the distance between the reaction flask and the
sunlamp at about 17 inches [20]. The solvent was evaporated to
dryness, and the residue was recrystallized from ethanol to afford
the pure product.
Single crystal X‐ray diffraction of 4. The suitable crystal of 4
with dimensions of 0.34 × 0.21 × 0.13 mm3 was mounted and
transferred to
a CCD‐equipped diffractometer. The X‐ray
diffraction data were collected using Mo kα (λ = 0.071073 nm)
radiation. Cell parameters were determined in the range of
2.44° < θ < 25.10° at the temperature of 296(2) K. A total of
3880 independent reflections (Rint = 0.0304) were obtained, among
which 1468 observed reflections with I > 2σ(I) were used for the
determination and refinement of the crystal structure in the range of
−18 ≤ h ≤ 29, −5 ≤ k ≤ 5, and −20 ≤ l ≤ 20, respectively. The
coordinates of atom were obtained by direct method. The results
were optimized by the least‐squares method with anisotropic
thermal parameters. The empirical formula was C6H5ClN4O2. The
molecular weight of compound 4 was 200.59. The crystal of
4 belongs to monoclinic, space group C2/c with a = 2.4812(8) nm,
α = 90°, b = 0.48451(16) nm, β = 124.829(3)°, c = 1.6821(6) nm,
γ = 90o, V = 1.6599(9) nm3, Z = 8, Dc = 1.605 g cm−3, μ = 0.431
mm−1, F(000) = 816. The maximum peak and the minimum
peak on the Fourier map were 191 and −353 e·nm−3, respectively.
The refinement was converged with R1 =0.0377, ωR2 =0.0917,
of which, w = 1/[s2(F0)2+(0.0377P)2+0.0000P], P = (F + 2F)/3,
S =1.072. All calculations were corrected by Lp. The crystal
structure resolve and correction were processed using SHELX‐97
program package [22, 23] on Founder −5166, respectively.
3‐(4‐Aminofurazan‐3‐yl)‐4,5‐dihydroxylmethylisoxazone (1).
Yield: 0.35 g (67.1%). m.p.143.55°C, T.p. 310.79°C (DSC, 10°C
min−1); 1H NMR (DMSO‐d6, 500 MHz) δ, ppm: 6.427(s, 2H,
NH2), 5.675(t, J = 6.0 Hz, 1H, OH), 5.121(t, J = 5.0 Hz, 1H,
OH), 4.731(d, J = 6.0 Hz, 2H, CH2), 4.628 (d, J = 5.0 Hz, 2H,
CH2); 13C NMR (DMSO‐d6, 125 MHz) δ, ppm: 170.644,
155.349, 151.150, 138.518, 115.689, 53.217, 51.862; IR (KBr)
υ: 3472, 3349(NH2), 3291(OH), 2956∼2869(CH2), 1635,1552
(furazan) cm−1; Anal. calcd for C7H8N4O4: C 39.62, H 3.774, N
26.41; found C 39.74, H 3.752, N 26.35; MS (EI) m/z(%): 212
(M+,18), 176(35), 155(100), 137(60), 109(35),68(50), 53 (85).
3‐(4‐Aminofurazan‐3‐yl)‐5‐tert‐butylisoxazone (2). Yield: 0.33 g
(64.5%). m.p. 162.82°C (DSC, 10°C min−1); H NMR(DMSO‐d6,
500 MHz) δ, ppm: 6.867(s, H, CH), 6.395(s, 2H, NH2), 1.376
1
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet.842

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Capture of 3‐Amino‐4‐oxycyanofurazan and Characterization of Isoxazole Product
[11] Wang, J.; Dong, H. S.; Huang, Y. G.; Li, J. S. Acta Chimica
Sinica 2006, 64, 158 (in Chinese).
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