Synthesis of 3-aroyl-4-(3-chromonyl)-2-pyrazolines

Article abstract of DOI:10.1002/jhet.5570390636

New 3-aroyl-4-(3-chromonyl)-2-pyrazolines have been synthesized by the reaction of 3-(3-aryl-3-oxopropenyl)chromen-4-ones and diazomethane. Some of these 2-pyrazolines have also been N-acylated with a mixture of anhydrous pyridine and acetic anhydride or

Full text of DOI:10.1002/jhet.5570390636

Nov-Dec 2002
Synthesis of 3-Aroyl-4-(3-chromonyl)-2-pyrazolines
1333
Albert Lévai*
Department of Organic Chemistry, University of Debrecen, P.O.Box 20,
H-4010 Debrecen, Hungary
József Jeko´´
ICN Hungary Co. Ltd., H-4440 Tiszavasvári, Hungary
Received August 21, 2002
Dedicated to Professor Dr. László To´´ke on the occasion of his 70th birthday.
New 3-aroyl-4-(3-chromonyl)-2-pyrazolines have been synthesized by the reaction of 3-(3-aryl-3-oxo-
propenyl)chromen-4-ones and diazomethane. Some of these 2-pyrazolines have also been N-acylated with a
mixture of anhydrous pyridine and acetic anhydride or propionic anhydride. Structures of all new compounds
have been elucidated by elemental analyses, mass spectrometry, ir and nmr spectroscopic measurements.
J. Heterocyclic Chem., 39, 1333(2002).
For the synthesis of pyrazolines, an especially popular
research which stimulates the efforts for the synthesis of
their newer representatives. Reaction of a ,b-enones with
diazomethane affords a simple and convenient procedure
to prepare a wide variety of pyrazolines for this purpose.
As far as the reaction of chalcones and realated a ,b-
unsaturated ketones with diazomethane is concerned, there
are conflicting data in the literature [12,13]. Our previous
studies [7-10] unequivocally proved that the sole isolable
product of this reaction is the appropriately substituted 2-
pyrazoline. Nevertheless, the utilization of newer sub-
strates may help to get additional information on the reac-
tion of the a ,b-enones with diazomethane. Therefore, in
our present paper, the reaction of a series 3-(3-aryl-3-oxo-
propenyl)chromen-4-ones 1-6 with dizomethane is
reported.
3-(3-Aryl-3-oxopropenyl)chromen-4-ones 1-6 were
allowed to react with diazomethane in a 1:1 mixture of
anhydrous methylene chloride and diethyl ether at ca. 0°.
3-Aroyl-4-(3-chromonyl)-2-pyrazolines 7-12 have been
obtained as sole isolable products (Scheme 1), the struc-
tures of which have been elucidated by means of elemental
analyses and spectroscopic measurements (vide infra).
procedure is based on the cycloaddition of diazoalkanes to
carbon-carbon double bonds. 1,3-Dipolar cycloaddition of
diazomethane and a ,b-unsaturated ketones has been stud-
ied by several research groups. Such a cycloaddition was
first published by Azzarello as early as 1906 who prepared
3-acetyl-4-phenyl-2-pyrazoline by the reaction of benza-
lacetone with diazomethane in anhydrous ether [1]. Later
on, 1,3-dipolar cycloaddition of a wide variety of chal-
cones and related a ,b-unsaturated ketones with dia-
zomethane was thoroughly investigated [2-13].
Experimental results proved that the only isolable products
of these reactions are 2-pyrazolines where the methylene
moiety of the diazomethane is connected to the b-carbon
atom of the starting a ,b-unsaturated ketones. Therefore,
this 1,3-dipolar cycloaddition is completely regioselective
and the initially formed 1-pyrazolines spontaneously
rearrange into their thermodynamically more stable 2-
pyrazoline isomers.
Previously we investigated the reaction of exocyclic
a ,b-unsaturated ketones with diazomethane in detail [14-
19]. It has been concluded that this 1,3-dipolar cycloaddi-
tion of these a ,b-enones is completely regioselective pro-
viding spiro-1-pyrazolines similarly to the above-men-
tioned a ,b-unsaturated ketones. The reaction is also stere-
ospecific, retaining the stereochemistry of the starting a ,b-
enones. Contrary to the above-mentioned cases, spiro-1-
pyrazolines obtained from exocyclic a ,b-unsaturated
ketones are stable compounds which do not suffer sponta-
neous isomerization into the corresponding 2-pyrazolines.
Our results are in harmony with those observed by others
[20-22].
Pyrazolines were found to possess considerable biologi-
cal and pharmacological activities. Their most important
effects are antimicrobial [23], immunosuppressive [24],
central nervous system [25], antiarrhytmic [26], antiin-
flammatory [27], antihypertensive [28], etc. activities. For
this reason, pyrazolines are useful substances in the drug
1
In the H nmr spectra of compounds 7-12, the three pro-
tons attached to the C-4 and C-5 carbon atoms of the pyra-
zoline ring gave an ABX spin system. Both the chemical
shifts and the coupling constant values (cf. Experimental)
13
reveal a 2-pyrazoline structure. C chemical shift data of

1334
Albert Lévai and J. Jeko´´
Vol. 39
the carbon atoms of the pyrazoline ring also prove the 2-
pyrazoline character deduced from the H nmr data. The 2-
pyrazolines as sole isolable products similarly to the
related a ,b-unsaturated ketones. N-Acylation of these 2-
pyrazolines can easily be performed to get new pyrazoline
derivatives for drug research
1
pyrazoline structure was further corroborated by their ir
spectra measured in potassium bromide discs. A character-
istic NH band was observed between 3232 and and 3288
-1
cm while the C=N band was detected between 1589 and
EXPERIMENTAL
-1
1598 cm . The two carbonyl bands at around 1640 and
-1
1610 cm also confirm the presence of an aroyl and
Melting points were determined with a Koffler hot-stage appa-
ratus and are uncorrected. 1H and 13C nmr spectra were recorded
on a Varian Gemini 200 spectrometer at 200/50 MHz in CDCl3 or
in DMSO-d6 (internal standard TMS, d = 0.0) at room tempera-
ture. The ir spectra (KBr discs) were obtained with a Perkin-
Elmer 16 PC instrument. Mass spectra were recorded on a VG
Trio-2 instrument. Elemental analyses were measured in-house
with a Carlo Erba 1106 EA instrument. TLC was performed on
Kieselgel 60 F254 (Merck) layer using hexane:acetone (7:3 v/v)
as eluent. Starting materials 1-6,13,14 were synthesized accord-
ing to known procedures [8, 30-32].
chromonyl units in the molecule.
All these spectroscopic data prove that the 1,3-dipolar
cycloaddition of the 3-(3-aryl-3-oxopropenyl)chromen-4-
ones 1-6 with diazomethane is completely regioselective
providing 1-pyrazolines, as initial cycloadducts which
rearrange into 2-pyrazolines 7-12, where the methylene
moiety of the diazomethane is attached to the b-carbon
atom of the a ,b-enone. The double bond of the 3-
chromonyl unit may also react with diazomethane as found
by Ghosh et al. [29] for similar chromone derivatives.
However, no traces of such cycloadducts could be detected
or isolated in the case of our substrates.
Synthesis of 3-Aroyl-4-(3-chromonyl)-2-pyrazolines 7-12 by the
Reaction of 3-(3-Aryl-3-oxopropenyl)chromen-4-ones 1-6 with
Diazomethane. General Procedure.
A mixture of 3-(3-aryl-3-oxopropenyl)chromen-4-one (1-6,
5.0 mmoles), diazomethane (15.0 mmoles), anhydrous methylene
chloride (30.0 ml) and diethyl ether (30.0 ml) was allowed to
stand in refrigerator for 48 hours, then the solvent was evaporated
under reduced pressure and the residue was crystallized from
methanol to obtain 3-aroyl-4-(3-chromonyl)-2-pyrazolines 7-12
(Scheme 1).
3-Benzoyl-4-(3-chromonyl)-2-pyrazoline (7).
This compound was obtained as white needles in 78% yield,
mp 193-194°; ir: 3232 (nNH), 1636 (nC=O), 1608 (nC=O), 1598
(nC=N) cm-1; 1H nmr (DMSO-d6): d 3.68 (1H, dd, J = 12.3, 3.1
Hz, 5-H), 3.97 (1H, dd, J = 12.3, 10.1 Hz, 5-H), 4.68 (1H, dd, J =
10.1, 3.1 Hz, 4-H), 7.32-8.20 (m, 9 arom. H); 13C nmr (DMSO-
d6): d 40.5 (C-4), 54.8 (C-5), 153.1 (C-3), 177.2 (C=O), 187.5
(C=O).
Anal. Calcd. for C19H14N2O3: C, 71.69; H, 4.43; N, 8.79.
Found: C, 71.72; H, 4.41; N, 8.76.
As a further proof of the 2-pyrazoline structure, N-acyla-
tion of selected examples of 3-aroyl-4-(3-chromonyl)-2-
pyrazolines described in our previous [8] and present
papers has also been performed. Compounds 8 and 10-14
were allowed to react with a mixture of anhydrous pyri-
dine and acetic anhyride or propionic anhydride to afford
their N-acylated derivatives 15-23 (Scheme 2). Structures
of these new 2-pyrazolines have been elucidated by ele-
mental analyses, ir and H and C nmr spectroscopic
measurements (cf. Experimental). Moreover, molecular
ions detected in their EI-ms spectra also corroborated their
structures determined by the above-mentioned techniques.
All these data prove that neither the 2-pyrazoline nor the
chromone ring suffered any rearrangement under these
acylating conditions.
4-(3-Chromonyl)-3-(4-methylbenzoyl)-2-pyrazoline (8).
This substance was isolated as white crystals in 61% yield, mp
164-165°; ir: 3246 (nNH), 1640 (nC=O), 1604 (nC=O), 1596
(nC=N) cm-1; 1H nmr (DMSO-d6): d 2.34 (3H, s, Me), 3.54 (1H,
dd, J = 12.4, 3.0 Hz, 5-H), 3.98 (1H, dd, J = 12.4, 10.1 Hz, 5-H),
4.54 (1H, dd, J = 10.1, 3.0 Hz, 4-H), 7.07-8.18 (m, 8 arom. H);
13C nmr (DMSO-d6): d 40.7 (C-4), 54.6 (C-5), 153.9 (C-3),
176.1 (C=O), 186.1 (C=O).
1
13
Anal. Calcd. for C20H16N2O3: C, 72.28; H, 4.85; N, 8.42.
Found: C, 72.33; H, 4.83; N, 8.44.
4-(3-Chromonyl)-3-(4-methoxybenzoyl)-2-pyrazoline (9).
This compound was prepared as white needles in 75% yield,
mp 108-109°; ir: 3388 (nNH), 1644 (nC=O), 1604 (nC=O), 1598
(nC=N) cm-1; 1H nmr (DMSO-d6): d 3.62 (1H, dd, J = 12.7, 3.2
Hz, 5-H), 3.78 (3H, s, Me), 3.94 (1H, dd, J = 12.7, 9.9 Hz, 5-H),
In conclusion, it has been established that the 1,3-dipolar
cycloaddition of 3-(3-aryl-3-oxopropenyl)chromen-4-ones
with diazomethane provides 3-aroyl-4-(3-chromonyl)-2-
4.66 (1H, dd, J = 9.9, 3.2 Hz, 4-H), 6.51-7.86 (m, 8 arom. H); 13
C
nmr (DMSO-d6): d 25.1 (OMe), 40.6 (C-4), 55.0 (C-5), 153.2
(C-3), 176.9 (C=O), 185.7 (C=O).

Nov-Dec 2002
Synthesis of 3-Aroyl-4-(3-chromonyl)-2-pyrazolines
1335
(nC=N) cm-1; 1H nmr (CDCl3): d 2.45 (3H, s, Me), 4.07 (1H, dd,
J = 12.0, 4.0 Hz, 5-H), 4.34 (1H, t, 12.0 Hz, 5-H), 4.57 (1H, dd, J
= 8.9, 4.0 Hz, 4-H), 7.06-8.26 (m, 8 arom. H); 13C nmr (CDCl3):
d 21.2 (Me), 43.5 (C-4), 50.2 (C-5), 152.2 (C-3), 170.3 (C=O),
177.0 (C=O), 186.2 (C=O); EI-ms: m/z 378 (M+)
Anal. Calcd. for C20H16N2O4: C, 68.96; H, 4.63; N, 8.04.
Found: C, 68.92; H, 4.65; N, 8.07.
4-(3-Chromonyl)-3-(4-fluorobenzoyl)-2-pyrazoline (10).
This compound was isolated as pale yellow plates in 73%
yield, mp 217-218°; ir: 3258 (nNH), 1636 (nC=O), 1608 (nC=O),
1598 (nC=N) cm-1; 1H nmr (DMSO-d6): d 3.58 (1H, t, J = 12.5
Hz, 5-H), 3.98 (1H, t, J = 12.5 Hz, 5-H), 4.54 (1H, dd, J = 8.7, 4.1
Hz, 4-H), 7.24-8.16 (m, 8 arom. H); 13C nmr (DMSO-d6): d 40.3
(C-4), 54.8 (C-5), 154.0 (C-3), 176.1 (C=O), 184.8 (C=O).
Anal. Calcd. for C19H13FN2O3: C, 67.86; H, 3.89; N, 8.33.
Found: C, 67.85; H, 3.91; N, 8.30.
Anal. Calcd. for C21H15FN2O4: C, 66.67; H, 3.99; N, 7.40.
Found: C, 66.65; H, 3.98; N, 7.42.
1-Acetyl-3-(4-chlorobenzoyl)-4-(3-chromonyl)-2-pyrazoline
(17).
This compound was isolated as pale yellow needles in 67%
yield, mp 212-213°; ir: 1684 (nC=O), 1644 (nC=O), 1610
1
(nC=O), 1586 (nC=N) cm-1; H nmr (CDCl3): d 2.44 (3H, s,
3-(4-Chlorobenzoyl)-4-(3-chromonyl)-2-pyrazoline (11).
Me), 4.06 (1H, dd, J = 11.7, 4.1 Hz, 5-H), 4.33 (1H, t, J = 11.7
Hz, 5-H), 4.54 (1H, dd, J = 8.7, 4.1 Hz, 4-H), 7.27-8.15 (m, 8
arom. H); 13C nmr (CDCl3): d 21.2 (Me), 43.5 (C-4), 50.3 (C-5),
154.2 (C-3), 170.4 (C=O), 177.0 (C=O), 186.3 (C=O); EI-ms:
m/z 394 (M+).
Anal. Calcd. for C21H15ClN2O4: C, 63.88; H, 3.83; N, 7.09.
Found: C, 63.85; H, 3.84; N, 7.11.
This substance was prepared as pale yellow needles in 66%
yield, mp 235-236°; ir: 3240 (nNH), 1632 (nC=O), 1614
(nC=O), 1598 (nC=N) cm-1; 1H nmr (DMSO-d6): d 3.59 (1H, t,
J = 12.8 Hz, 5-H), 4.01 (1H, t, J = 12.8 Hz, 5-H), 4.56 (1H, dd,
J = 8.6, 3.9 Hz, 4-H), 7.44-8.16 (m, 8 arom. H); 13C nmr
(DMSO-d6): d 40.7 (C-4), 54.8 (C-5), 154.1 (C-3), 176.1
(C=O), 185.0 (C=O).
1-Acetyl-3-(4-bromobenzoyl)-4-(3-chromonyl)-2-pyrazoline
(18).
Anal. Calcd. for C19H13ClN2O3: C, 64.69; H, 3.71; N, 7.94.
Found: C, 64.71; H, 3.69; N, 7.97.
This substance was prepared as white plates in 84% yield, mp
190-191°; ir: 1682 (nC=O), 1646 (nC=O), 1610 (nC=O), 1582
(nC=N) cm-1; 1H nmr (CDCl3): d 2.44 (3H, s, Me), 4.06 (1H, dd,
J = 12.5, 4.0 Hz, 5-H), 4.34 (1H, t, J = 12.5 Hz, 5-H), 4.54 (1H,
dd, J = 8.5, 4.0 Hz, 4-H), 7.29-8.17 (m, 8 arom. H); 13C nmr
(CDCl3): d 21.2 (Me), 43.5 (C-4), 50.3 (C-5), 154.2 (C-3), 170.4
(C=O), 177.0 (C=O), 186.8 (C=O); EI-ms: m/z 440/442 (M+).
Anal. Calcd. for C21H15BrN2O4: C, 57.42; H, 3.44; N, 6.37.
Found: C, 57.44; H, 3.42; N, 6.39.
3-(4-Bromobenzoyl)-4-(3-chromonyl)-2-pyrazoline (12).
This compound was obtained as pale yellow needles in 89%
yield, mp 232-233°; ir: 3252 (nNH), 1629 (nC=O), 1605 (nC=O),
1589 (nC=N) cm-1; 1H nmr (DMSO-d6): d 3.58 (1H, t, J = 12.8
Hz, 5-H), 4.02 (1H, t, J = 12.8 Hz, 5-H), 4.54 (1H, dd, J = 8.8, 4.1
Hz, 4-H), 7.47-8.17 (m, 8 arom. H); 13C nmr (DMSO-d6): d 40.7
(C-4), 54.8 (C-5), 154.1 (C-3), 176.1 (C=O), 185.2 (C=O).
Anal. Calcd. for C19H13BrN2O3: C, 57.45; H, 3.30; N, 7.05.
Found: C, 57.48; H, 3.28; N, 7.08.
1-Acetyl-4-(3-chromonyl)-3-(1-naphthoyl)-2-pyrazoline (19).
N-Acylation of 3-Aroyl-4-(3-chromonyl)-2-pyrazolines 8, 10-14
in a Mixture of Anhydrous Pyridine and Acetic anhydride or
Propionic anhydride. General Procedure.
This compound was isolated as white needles in 69% yield, mp
155-156°; ir: 1680 (nC=O), 1644 (nC=O), 1610 (nC=O), 1592
(nC=N) cm-1; 1H nmr (CDCl3): d 2.28 (3H, s, Me), 4.14 (1H, dd,
J = 12.6, 3.7 Hz, 5-H), 4.37 (1H, t, 12.6, 5-H), 4.64 (1H, dd, J =
8.8, 3.7 Hz, 4-H), 7.27-8.40 (m, 11 arom. H); 13C nmr (CDCl3): d
21.1 (Me), 43.3 (C-4), 50.7 (C-5), 154.5 (C-3), 170.6 (C=O),
177.2 (C=O), 190.7 (C=O); EI-ms: m/z 410 (M+).
A mixture of 3-aroyl-4-(3-chromonyl)-2-pyrazoline (8, 10-14,
2.0 mmoles), anhydrous pyridine (5.0 ml) and acetic anhydride
(10.0 ml) or propionic anhydride (10.0 ml) was heated at 80° for
3 hours, then poured into water. The precipitate was collected by
filtration, washed with water, and crystallized from methanol to
afford 2-pyrazolines 15-23 (Scheme 2).
Anal. Calcd. for C25H18N2O4: C, 73.16; H, 4.42; N, 6.82.
Found C, 73.19; H, 4.44; N, 6.80.
1-Acetyl-4-(3-chromonyl)-3-(4-methylbenzoyl)-2-pyrazoline
1-Acetyl-4-(3-chromonyl)-3-(2-naphthoyl)-2-pyrazoline (20).
(15).
This substance was obtained as pale yelnlow needles in 63%
This compound was isolated as white plates in 71% yield, mp
130-131°; ir: 1682 (nC=O), 1644 (nC=O), 1606 (nC=O), 1588
(nC=N) cm-1; 1H nmr (CDCl3): d 2.43 (3H, s, Me), 2.49 (3H, s,
Me), 4.09 (1H, dd, J = 12.6, 3.9 Hz, 5-H), 4.34 (1H, t, J = 12.6
Hz, 5-H), 4.60 (1H, dd, J = 8.5, 3.9 Hz, 4-H), 7.24-8.18 (m, 8
arom. H); 13C nmr (CDCl3): d 21.5 (Me), 29.5 (Me), 43.5 (C-4),
50.1 (C-5), 154.l (C-3), 170.4 (C=O), 176.9 (C=O), 187.4 (C=O);
EI-ms: m/z 374 (M+).
yield, mp 149-150°; ir: 1674 (nC=O), 1644 (nC=O), 1609
1
(nC=O), 1684 (nC=N) cm-1; H nmr (CDCl3): d 2.49 (3H, s,
Me), 4.12 (1H, dd, J = 12.3, 3.4 Hz, 5-H), 4.38 (1H, t, J = 12.3
Hz, 5-H), 4.63 (1H, dd, J = 8.5, 3.4 Hz, 4-H), 7.26-8.87 (m, 11
arom. H); 13C nmr (CDCl3): d 21.3 (Me), 43.7 (C-4), 50.3 (C-5),
154.2 (C-3), 171.0 (C=O), 177.1 (C=O), 187.6 (C=O); EI-ms:
m/z 410 (M+).
Anal. Calcd. for C25H18N2O4: C, 73.16; H, 4.42; N, 6.82.
Found: C, 73.12; H, 4.40; N, 6.85.
Anal. Calcd. for C22H18N2O4: C, 70.58; H, 4.84; N, 7.48.
Found: C, 70.61; H, 4.83; N, 7.50.
3-(4-Bromobenzoyl)-4-(3-chromonyl)-1-propionyl-2-pyrazoline
(21).
1-Acetyl-4-(3-chromonyl)-3-(4-fluorobenzoyl)-2-pyrazoline
(16).
This compound was prepared as white plates in 76% yield, mp
142-143°; ir: 1680 (nC=O), 1644 (nC=O), 1610 (nC=O), 1582
This substance was isolated as white needles in 69% yield, mp
202-203°; ir: 1682 (nC=O), 1648 (nC=O), 1610 (nC=O), 1598
1
(nC=N) cm-1; H nmr (CDCl3): d 1.26 (3H, t, J = 7.3 Hz,

1336
Albert Lévai and J. Jeko´´
Vol. 39
(1959).
CH2CH3), 2.81 (2H, m, CH2CH3), 4.06 (1H, dd, J = 12.5, 3.9 Hz,
5-H), 4.34 (1H, t, J = 12.5 Hz, 5-H), 4.53 (1H, dd, J = 8.5, 3.9 Hz,
4-H), 7.28-8.13 (m, 8 arom. H); 13C nmr (CDCl3): d 8.6 and 27.0
(Et), 43.1 (C-4), 50.5 (C-5), 154.2 (C-3), 173.8 (C=O), 176.9
(C=O), 186.8 (C=O); EI-ms: m/z 452/454 (M+).
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Anal. Calcd. for C22H17BrN2O4: C, 58.29; H, 3.78; N, 6.18.
Found: C, 58.32; H, 3.76; N, 6.20.
4-(3-Chromonyl)-3-(1-naphthoyl)-1-propionyl-2-pyrazoline
(22).
This compound was isolated as pale yellow plates in 68%
yield, mp 116-117°; ir: 1678 (nC=O), 1644 (nC=O), 1610
(nC=O), 1592 (nC=N) cm-1; 1H nmr (CDCl3): d 1.16 (3H, t, J =
7.5 Hz, CH2CH3), 2.69 (2H, m, CH2CH3), 4.12 (1H, dd, J =
11.8, 3.9 Hz, 5-H), 4.38 (1H, t, J = 11.8 Hz, 5-H), 4.61 (1H, dd, J
= 8.7, 3.9 Hz, 4-H), 7.33-8.41 (m, 11 arom. H); 13C nmr (CDCl3):
d 8.5 and 26.9 (Et), 42.9 (C-4), 50.9 (C-5), 154.3 (C-3), 174.0
(C=O), 177.1 (C=O), 190.7 (C=O); EI-ms: m/z 424 (M+).
Anal. Calcd. for C26H20N2O4: C, 73.57; H, 4.75; N, 6.59.
Found: C, 73.61; H, 4.73; N, 6.61.
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4-(3-Chromonyl)-3-(2-naphthoyl)-1-propionyl-2-pyrazoline
(23).
This substance was prepared as pale yellow needles in 67%
yield, mp 162-163°; ir: 1678 (nC=O), 1640 (nC=O), 1612
(nC=O), 1584 (nC=N) cm-1; 1H nmr (CDCl3): d 1.29 (3H, t, J =
11.4 Hz, CH2CH3), 2.86 (2H, m, CH2CH3), 4.12 (1H, dd, J =
11.5, 4.0 Hz, 5-H), 4.38 (1H, t, J = 11.7, 5-H), 4.62 (1H, dd, J =
8.5, 4.0 Hz, 4-H), 7.27-8.21 (m, 11 arom. H); 13C nmr (CDCl3): d
8.7 and 27.1 (Et), 43.3 (C-4), 50.4 (C-5), 154.2 (C-3), 173.9
(C=O), 177.0 (C=O), 187.6 (C=O); EI-ms: m/z 424 (M+).
Anal. Calcd. for C26H20N2O4: C, 73.57; H, 4.75; N, 6.59.
Found: C, 73.54; H, 4.76; N, 6.57.
Acknowledgements.
Thanks are due to the Hungarian National Research
Foundation (Grant No. OTKA T034123) for the financial sup-
port. Technical assistance of Mrs. M. Nagy is highly appreciated.
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(1974); Chem. Abstr., 82, 57684 (1975).
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