Reactions of 3-amino-4-methylfurazan with nitrating agents

Article abstract of DOI:10.1007/s11172-006-0027-3

Depending on the type of nitrating agent and the reaction temperature, nitration of 3-amino-4-methylfurazan 1 gives either nitramine or the products of formal oxidation of the amino group, namely, nitroso-, nitro-, azo-, and azoxyfurazans. The methyl group of compound 1 is resistant against all the nitrating agents studied.

Full text of DOI:10.1007/s11172-006-0027-3

Russian Chemical Bulletin, International Edition, Vol. 54, No. 7, pp. 1715—1719, July, 2005
1715
Reactions of 3ꢀaminoꢀ4ꢀmethylfurazan with nitrating agents
A. B. Sheremetevꢀ and N. S. Aleksandrova
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences,
4
7 Leninsky prosp., 119991 Moscow, Russian Federation.
Fax: +7 (095) 135 5328. Eꢀmail: sab@ioc.ac.ru
Depending on the type of nitrating agent and the reaction temperature, nitration of 3ꢀaminoꢀ
4
ꢀmethylfurazan 1 gives either nitramine or the products of formal oxidation of the amino
group, namely, nitrosoꢀ, nitroꢀ, azoꢀ, and azoxyfurazans. The methyl group of compound 1 is
resistant against all the nitrating agents studied.
Key words: aminofurazans, nitramines, nitraminofurazans, nitrofurazans, nitration.
Nitraminofurazans are of interest as potential exploꢀ
sives and components of rocket propellants and gas genꢀ
erating mixtures. The chemistry of these compounds has
been surveyed in reviews.1
The change in the reaction temperature from –20 to 30 °C
barely affects the product yield, which amounts to
65—80%. The reaction of compound 1 with nitrating
mixtures such as HNO /H SO , HNO /H SO /SO ,
—3
3
2
4
3
2
4
3
The nitration of secondary aminofurazans with, for
HNO /Ac O, and KNO /H SO devoid of nitrogen oxꢀ
3 2 3 2 4
4
,5
5—10
example, HNO /(CF CO) O,
HNO /Ac O,
or
ides proceeds in a similar way to give nitramine 2 in
75—85% yield. The use of Nꢀacetylated derivative 3 as the
starting compound for nitration gives nitramine 2 in the
same yield.
3
3
2
3
2
N O (see Refs 5, 7) is known to yield nitramines. The
2
5
type and the amount of byꢀproducts have not been anaꢀ
lyzed. It was only reported that the use of traditional
HNO /H SO mixtures is accompanied by side nitrolysis
3
2
4
of the N—CH bond, resulting in the formation of primary
nitraminofurazans.10
Scheme 1
The information on nitration of primary aminofurazans
is limited. Nitramines can be obtained by reactions with
1
1
N O , HNO (see Refs 5, 12—15), or NaNO /H SO
2
5
3
3
2
4
(
see Ref. 10), HNO /H SO (see Refs 5, 13), and
3 2 4
HNO /AcOH (see Ref. 16) mixtures. Treatment of
3
aminofurazans with excess N O (see Refs 12, 17) or
2
5
NO BF (see Refs 17, 18) affords nitro derivatives of
The reaction of amine 1 with concentrated HNO3
2
4
furazan; however, this process also goes through nitramine
formation.
containing even a small amount of nitrogen oxides (N O
2
3
and N O ) is accompanied by the formation of substantial
2
4
To continue the research into the reaction of furazan
derivatives with nitrating reagents, we studied the nitraꢀ
tion of 3ꢀaminoꢀ4ꢀmethylfurazan 1 as the simplest and
the most readily available model compound.
amounts of side products. Detailed analysis of the reacꢀ
1
14
tion mixtures ( H and N NMR, TLC, GLC, GC/MS;
comparison with authentic samples) has shown that nitroꢀ,
nitrosoꢀ, azoꢀ, and azoxyfurazans and α,αꢀdinitroacetoꢀ
nitrile are the main impurities. The byꢀproducts are
apparently formed due to the diazotization and furꢀ
ther transformations of the intermediate diazonium salt
(Scheme 2). The possibility of preparing nitrofurazan 5 by
1
9
The furazan ring exerts a strong electronꢀwithdrawing
2
effect on the groups it bears. As a consequence, aminoꢀ
2
0
furazans are very weak bases. This fact allows one to
carry out nitration for amines rather than for derivatives
with protected amino groups (the technique normally used
2
2
diazotization of compound 2 has been reported. Nitroꢀ
gen oxides present in the reaction mixture serve as the
source of nitrite ions required to perform this transforꢀ
mation.
2
1
for nitrating other primary amines ).
We showed that the outcome of the reaction of comꢀ
pound 1 with 100% nitric acid depends on the content of
nitrogen oxides in the acid. The acid containing no nitroꢀ
gen oxides smoothly transforms compound 1 into nitrꢀ
amine 2 (Scheme 1). The reaction is carried out either in
the acid or in its mixtures with organochlorine solvents.
Nitroso compound 6 might be formed with participaꢀ
•
tion of the NO radical or through substitutive nitrosation
with preliminary electron redistribution between diazoꢀ
nium salt 4 and species present in the reaction mixture.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1665—1669, July, 2005.
066ꢀ5285/05/5407ꢀ1715 © 2005 Springer Science+Business Media, Inc.
1

1
716
Russ.Chem.Bull., Int.Ed., Vol. 54, No. 7, July, 2005
Sheremetev and Aleksandrova
Scheme 2
2
3
Nitroso compound 6 dimerizes to give diazene dioxide 7.
of nitric acid has been converted into N O (on treatment
2 5
with trifluoroacetic anhydride or P O ), these are the maꢀ
2 5
Pure compound 6 2 in a CH Cl solution or without
3
2
2
a solvent undergoes disproportionation typical of
nitroso compounds,2 resulting in the formation of comꢀ
pounds 5, 8, and 9. The diazotization of compound 1,
jor reaction products at a 10ꢀfold molar excess of the
nitrating mixture. When an equimolar amount of this mixꢀ
ture is used, the desired nitramine 2 can be obtained in a
yield of 75—80%.
4
2
like that of other aminofurazans, is accompanied by openꢀ
ing of the furazan ring to give αꢀcyanoxime 10 (see
Nitronium salts are usually potent reagents for Nꢀniꢀ
2
9
Ref. 22, 25). According to the typical cyanoxime reactivꢀ
tration of amines. However, the yield of nitramine
formed upon nitration of both amine 1 and its Nꢀacetyl
derivative with nitronium tetrafluoroborate in MeCN or
CH Cl at 0—5°C is not more than 65%. Azofurazan 9 is
2
6
ity, compound 10 is nitrated under the reaction condiꢀ
tions being converted into dinitro derivative 11 (see
Ref. 27).
2
2
The number and the yield of byꢀproducts depend on
the amount of nitrogen oxides and the reaction temperaꢀ
ture. After the nitration of amine 1 with anhydrous nitric
acid containing ~10% N O , no nitramine 2 was isolated.
formed as the major byꢀproduct (up to 30% at elevated
temperatures). Note that the formation of azo comꢀ
30
pounds has been detected previously upon treatment of
5ꢀaminoꢀ1,2,4ꢀtriazole with NO BF . Since no nitrosoꢀ
2
4
2
4
When the nitrogen oxide content was ∼ 2%, the yield of
nitramine 2 was 40—45%. The nitration carried out at
furazan 6, its dimer 7, or azoxy derivative 8 has been
found upon the reaction of amine 1 with NO BF , it is
2
4
–
5—0 °C resulted in the formation of nitroso compound 6
reasonable to assume that azo compound 9 is formed by a
and its dimer 7.
route differing from that shown in Scheme 2. Probably,
N,Nꢀdinitration of the amino group takes place as a side
Yet another reagent widely used28 for nitration is N O .
29
2
5
The reaction of N O with primary aminofurazans may
process (Scheme 3), and labile compound 12 decomꢀ
poses, similarly to N,Nꢀdibromoamines, to generate
nitrene 13, which dimerizes into azo compound 9. Howꢀ
ever, nitrеne 13 could arise upon the oxidation of nitrꢀ
amine 2, as takes place in the electrolysis of nitraminoꢀ
2
5
1
1,12,17
yield different products.
We studied the nitration
of compound 1 with the HNO /N O mixture and
3
2
5
HNO /(CF CO) O and HNO /P O mixtures in which
3
3
2
3
2
5
N O is formed in situ. Unlike N O , the presence of up
2
5
2
4
1
4
to ∼ 5% N O in a reaction mixture containing excess
furazans.
2
5
nitrating reagent increases the yield of nitramine 2
to 96%). However, further increase in the concentration
of N O gives rise to side formation of nitroꢀ (5) and
As an attempt to improve the outcome of nitration
with NO BF , we carried out preliminary silylation of the
(
2
4
amino group in compound 1 by the procedure we develꢀ
2
5
3
1
azoxyfurazans (8). For mixtures in which more than 80%
oped previously. The nitration of the silyl derivative 14

Nitration of 3ꢀaminoꢀ4ꢀmethylfurazan
Russ.Chem.Bull., Int.Ed., Vol. 54, No. 7, July, 2005
1717
Scheme 3
Scheme 4
Table 1. Reference signals in the H and 14N NMR spectra, δ
1
in CH Cl at –30 °C furnished nitramine 2 in 89—93%
2
2
yield (Scheme 4).
Previously,3
2,33
it was found that borylation of the
1H NMR
14N NMR
Compound
amino group bonded to the furazan ring increases its reꢀ
activity. We were the first to demonstrate that the reaction
of borylated amine with nitronium tetrafluoroborate is
accompanied by cleavage of the N—B bond to give
nitramine. For example, nitramine 2 was obtained in
2
5
6
7
8
9
2.43
2.71
2.65
–41.0 (NHNO2)
–32.4 (NO2)
515.1 (NO)
–68.2 (N→O)
–66.5 (N→O)
—
2.58
2.56, 2.83
2.63
8
5% yield on treatment of derivative 15 with NO BF
2 4
at –30 °C.
It is noteworthy that nitration of alkylaromatic comꢀ
pounds is often accompanied by oxidative transformaꢀ
tions of the alkyl groups and substitution of a nitro group
for their αꢀhydrogen atoms. The methyl group attached
to the furazan ring is stable against nitrating agents; in
none of the experiments, were products resulting from
nitration or oxidation of this group detected. Only reꢀ
cently,3 were the conditions found for involving the
methyl group in the reaction.
Thus, it was shown that a number of reagents and
procedures are suitable for Nꢀnitration of the amino group
attached to the furazan ring. The presence of nitrosating
species in the reaction mixture is the key factor decreasing
the yield of the target nitramine.
Mass spectra were recorded on Finnigan MAT INCOSꢀ50
and Varian MAT CHꢀ111 instruments (EI, 70 eV).
The reactions were monitored and the product purity was
checked by TLC on Silufol UVꢀ254 plates. For analysis of comꢀ
pounds 5, 6, 9, and 11, a pentane/CH Cl mixture (1 : 3 v/v)
2
2
was used as the eluent, while for compounds 1, 7, 8, a
MeCN/CCl mixture (1 : 4) was used. The spots corresponding
4
to all of the starting compounds and final products luminesce in
the UV range. The spots for nitrosoꢀ, nitroꢀ, azoꢀ, and azoxy
compounds can also be visualized by spraying the plates with a
5% solution of diphenylamine in hexane; the spots become
colored.
4
GLC analysis was carried out on a Biochomꢀ1 chromatoꢀ
graph equipped with a quartz capillary column (0.2 mm×20 m,
SEꢀ54 phase) with a flame ionization detector and helium as the
carrier gas.
1
9
The initial compound 1 and the authentic samples of prodꢀ
ucts 2,12 5, 6, 7, 8, 9,37 and 11 were prepared by known
procedures. Characteristics of the products corresponded to those
published previously.35
35
23 23 23
27
Experimental
Melting points were determined in a Gallenkamp hot stage,
Sanyo. 1H and N NMR spectra for natural isotope abunꢀ
dances were recorded on a Bruker AMꢀ300 spectrometer operꢀ
Nitration of 3ꢀaminoꢀ4ꢀmethylfurazan (1). A. Treatment with
14
100% HNO . Amine 1 (1.98 g, 20 mmol) was added in small
3
portions at –10 °C to a vigorously stirred mixture of colorless
100% nitric acid (ρ = 1.5 g cm–3, 5 mL) and CH Cl (5 mL).
ating at 300.13 and 21.5 МHz, respectively, in acetoneꢀd . The
6
2
2
1
H NMR chemical shifts (in the δ scale) were measured relative
After 1 h, the reaction mixture was poured on ice, the resulting
emulsion was extracted with ether (3×30 mL), and the extract
was dried with MgSO4 and concentrated. Recrystallization
from CF CO H/CCl gave 0.7 g (22%) of compound 2, m.p.
14
to the solvent as an internal standard, while the N NMR
chemical shifts were referred to external nitromethane. The refꢀ
erence NMR signals3 used in the analysis of reaction mixtures
are presented in Table 1.
5
3
2
4
–
1
88—89 °C. IR (KBr), ν/cm : 3228, 3164, 3120, 3008, 2948,

1
718
Russ.Chem.Bull., Int.Ed., Vol. 54, No. 7, July, 2005
Sheremetev and Aleksandrova
1
1
6
612, 1576, 1536, 1472, 1448, 1392, 1244, 1236,1224, 1040,
References
+
+
000, 936, 900. MS, m/z: 144 [M ], 97 [M – NO – H],
2
+
7 [M – NO – H – NO]. Found (%): C, 24.96; H, 2.75;
2
1
. A. B. Sheremetev, Ros. Khim. Zhurn. (Zhurn. Ros. khim. oꢀva
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N, 38.91. C H N O (144.09). Calculated (%): C, 25.01;
H, 2.80; N, 38.88.
3
4
4
3
B. Treatment with 100% HNO3 and N O4 (2%). Amine 1
2
2
3
(
0.99 g, 10 mmol) was added in small portions at –5 °C to a
vigorously stirred mixture of colorless 100% nitric acid (ρ =
. A. B. Sheremetev and I. L. Yudin, Usp. Khim., 2003, 72, 93
Russ. Chem. Rev., 2003, 72, 87 (Engl. Transl.)].
–
3
1.5 g cm , 5 mL) and N O (0.15 g). After 1 h, the reaction
2 4
[
mixture was allowed to warm up to ~20 °C and poured on ice.
The product was extracted with ether (3×30 mL) and the extract
was washed with cold water and dried with MgSO . The resultꢀ
ing solution was analyzed by TLC, GLC, and GC/MS (the
products were identified by comparison with authentic samples).
After evaporation of the solvent, the mixture was analyzed by
NMR. The yields of nitramine 2 were 40—45 %.
4
5
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4
6
C. Treatment with NO BF . Compound 1 (0.99 g, 10 mmol)
2
4
was added in small portions to a vigorously stirred suspension of
NO BF (1.5 g, 11.3 mol) in CH Cl (20 mL) cooled to 0 °C.
1
987, 412.
2
4
2
2
7
8
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The reaction mixture was stirred for 1 h and the temperature was
slowly raised to 5 °C. The products were analyzed as in proceꢀ
dure B. To isolate compound 2, the reaction mixture was treated
as in procedure A to give 0.9 g (63%) of compound 2 identical to
an authentic sample.
Nitration of 4ꢀmethylꢀ3ꢀtrimethylsilylaminofurazan (14).
A suspension of aminofurazan 1 (0.99 g, 10 mmol) and hexaꢀ
methyldisilazane (2 g, 12.4 mol) in toluene (10 mL) was reꢀ
fluxed for 1 h under dry argon. The excess of the silylating
reagent and the solvent were removed in vacuo from the resultꢀ
ing solution of compound 14. The residue was dissolved in anꢀ
hydrous CH Cl (25 mL) and cooled to –30 °C, and NO BF
9
1
2
2
2
4
3
(
1.5 g, 11.3 mol) was added. The temperature was gradually
1
1
1
raised to 0 °C and the mixture was kept until the reaction was
completed (TLC monitoring). Then the solvent and all volatile
products were evaporated in vacuo. The residue was dissolved in
ether (50 mL) and the solution was washed with 20% hydroꢀ
chloric acid (2×20 mL) and dried with MgSO . After the reꢀ
moval of the solvent, the product was frozen out of CH Cl to
1
4
2
2
give 1.31 g (91%) of nitramine 2.
Nitration of 3ꢀdibutylborylaminoꢀ4ꢀmethylfurazan (15). A susꢀ
pension of amine 1 (0.99 g, 10 mmol) and BBu (1.8 g, 10.4 mol)
3
1
1
in xylene (10 mL) was refluxed for 2 h under dry argon. The
solvent was removed in vacuo from the resulting solution of
compound 15. The residue was dissolved in cold anhydrous
CH Cl2 (20 mL) and the solution was cooled to –30 °C and
slowly displaced by argon into a different flask containing a
suspension of NO BF4 (1.5 g, 11.3 mol) in CH Cl2 (20 mL)
2
2
004, 40, 922 [Russ. J. Org. Chem., 2004, 40, 884 (Engl.
2
2
Transl.)].
vigorously stirred at –30 °C. The reaction mixture was stirred for
h at –30 °C and the temperature was slowly raised to 0 °C. The
1
6. A. V. Sergievskii, T. V. Romanova, S. F. Melnikova, and
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2
mixture was stirred for 2 h at this temperature, a mixture of
CH Cl (5 mL) and methanol (5 mL) was added dropwise, the
temperature was allowed to increase to ~20°C, the mixture was
kept for 2 h, and the solvent and all volatile products were
removed in vacuo. The residue was purified as described in the
previous experiment to give 1.2 g (85 %) of nitramine 2.
2
2
1
1
1
The work was partially financially supported by the
Federal Target Program "Integration of Science and
Higher Education of Russia for 2002—2006" (State Conꢀ
tract I0667).
2

Nitration of 3ꢀaminoꢀ4ꢀmethylfurazan
Russ.Chem.Bull., Int.Ed., Vol. 54, No. 7, July, 2005
1719
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Received March 14, 2005;
in revised form May 3, 2005