Synthesis of new haloderivatives of benzo[f]quinoline and 4,7-phenanthroline

Article abstract of DOI:10.1134/S1070428009110189

By condensations of 2-naphthylamine and 6-aminoquinoline with halogen-substituted benzaldehydes, 3-acetylpyridine and acetophenone derivatives new 1,3-diaryl(heteryl)benzo-[f]quinolines and 4,7-phenanthrolines were synthesized containing atoms of fluorine, bromine, and chlorine in the phenyl rings.

Full text of DOI:10.1134/S1070428009110189

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2009, Vol. 45, No. 11, pp. 1686−1690. © Pleiades Publishing, Ltd., 2009.
Original Russian Text © N.G. Kozlov, K.N. Gusak, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 11, pp. 1692−1696.
Synthesis of New Haloderivatives of Benzo[f]quinoline
and 4,7-Phenanthroline
N. G. Kozlov and K. N. Gusak
FaInstitute of Physical Organic Chemistry, National Academy of Sciences of Belarus,
Minsk, 220072 Belarus
e-mail: loc@ifoch.bas-net.by
Received February 18, 2009
Abstract—By condensations of 2-naphthylamine and 6-aminoquinoline with halogen-substituted benzaldehydes,
3-acetylpyridine and acetophenone derivatives new 1,3-diaryl(heteryl)benzo-[f]quinolines and 4,7-phenanthrolines
were synthesized containing atoms of fluorine, bromine, and chlorine in the phenyl rings.
DOI: 10.1134/S1070428009110189
In this research we for the first time fulfilled the
synthesis of halosubstituted benzo[f]quinolines and 4,7-
phenanthrolines proceeding from 2-naphthylamine (I), 6-
aminoquinoline (II), 4-(2-fluorobenzyloxy)-, p-fluoro-, p-
chloro-, p-bromobenzaldehyde (III–VI), p-chloro-, p-
bromoacetophenone, and 3-acetylpyridine (VII–IX).
The introduction of a halogen atom into a molecule of
a heterocyclic compound leads to extension of its
synthetic opportunities and of the range of its physiological
action [1, 2].
The published information on the synthesis of chlorine-
substituted benzo[f]quinolines and 4,7-phenanthrolines [2–
4] concerned the substitution of hydroxy group by the
treatment of POCl3 and PCl5 of the corresponding
hydroxy derivatives prepared along Conrad−Limpach and
Knorr reactions from 2-naphthylamine, 6-aminoquinoline,
or p-phenylenediamine and esters of β-oxo and β-di-
carboxylic acids. The direct halogenation of aza-
phenanthrenes requires stringent conditions due to
hindering the electrophilic substitution. The bromination
of 4,7-phenanthroline is carried out in oleum and results
in an inseparable mixture of mono-, di-, and tribromo
derivatives [5].
The condensation of amines I, II, aldehydes III–VI,
and methyl ketones VII–IX was carried out by boiling
for 4–6 h of a solution of equimolar amounts of the
reagents in 1-butanol in the presence of concn. HCl as
a catalyst. In 38–55% yield we obtained previously
unknown 1,3-diarylbenzo[f]quinolines X, XI and 1,3-
diaryl-4,7-phenanthrolines XII–XVI containing halogen
atoms in phenyl substituents, and also fluoro derivatives
of 3-aryl-1-(3-pyridyl)-benzo[f]quinoline XVII, XVIII.
As follows from the results of our previous
investigations [6–8] the reaction proceeds through the
stage of azomethine XIX–XXIV formation that further
reacts with the methyl ketone along the known mehanism
[9] involving the addition of the CH-acid to the C=N bond
of the azomethine and dehydrocyclization of the obtained
adduct A into benzo[f]quinoline X, XI, XVII, XVIII or
4,7-phenanthroline XII–XVI respectively. In the presence
of HCl formed aza- and diazaphenanthrene
hydrochlorides that on treating with ammonium hydroxide
furnished free bases X–XVIII.
The three-component condensation of arylamines,
aldehydes, and CH-acids that we have developed for the
synthesis of polyfused azaaromatic compounds [6–8]
provides a possibility to introduce halogen atoms into the
molecule of the heterocycle simultaneously with the
formation of the azaphenanthrene framework when
synthons contain halogen atoms. The variation of
substituents in the molecules of initial reagents makes it
possible to introduce into the azaphenanthrene structure
both identical and different halogen atoms, and also to
obtain compounds containing alongside the halogen
another pharmacophore atoms and groups.
To prove the involvement of azomethines in the
formation of the azaphenanthrene structure we carried
out the condensation of amines I, II with aldehydes III–
1686

SYNTHESIS OF NEW HALODERIVATIVES OF BENZO[f]QUINOLINE
1687
Scheme.
NH2
R
O
X
+
I, II
N
R'
VII_IX
O
X
XIX_XXIV
R
III_VI
R
R
'
R
'
R
O
O
NH
N
'
R
R
X
X
XXV_XXVIII
X_XVIII
A
R = F (III, XII, XVII, XIX, XXII, XXV), Cl (IV, X, XI, XIII, XV, XX, XXIII, XXVI), Br (V, XIV, XVI, XXIV, XXVII, XXVIII),
'
OCH2C6H4-2-F (VI, XVIII, XXI); R = 4-ClC6H4 (VII, X, XI, XIII, XV, XXVI, XXVII), 4-BrC6H4 (VIII, XI, XV, XVI, XXVIII),
3-pyridyl (IX, XVII, XVIII, XXV); X = CH (I, X, XI, XVII, XVIII–XXI), N (II, XII–XVI, XXII–XXIV).
'
VI, and the obtained Schiff bases XIX–XXIV were
brought into the reaction with acetophenones VII, VIII
or with 3-acetylpyridine (IX) under the above described
conditions. The corresponding benzoquinolines X, XI,
XVII, XVIII and phenanthrolines XII–XVI were
obtained in 40–56% yield.
It should be noted that even in 1-butanol we did not
always prevented the chalcones formation. Minor
quantities of compounds XXVI–XXVIII were isolated
alongside the target 4,7-phenanthrolines XIII, XIV, XVI
in the reactions of acetophenones VII, VIII both with
arylmethylene-6-aminoquinolines XXIII, XXIV and
6-aminoquinoline (II) and aldehydes IV, V evidently
because the nucleophilic activity of the amino group was
decreased and the reactivity of 6-aminoquinoline was
diminished compared to the 2-naphthylamine due to the
effect of the electronegative nitrogen atom of the quinoline
ring in amine II, and also because of decreased
polarization and the chemical activity of the azomethine
bond. Only in the case of p-fluoro substituent that to the
highest extent activated the carbonyl group of aldehyde
III and the azomethine bond in the molecule of Schiff
base XXII owing to the –I-effect 4,7-phenanthroline XII
formed selectively with the maximum yield (54%) for
phenanthrolines.
We failed to isolate intermediate aminoketones A.
Under mild conditions commonly applied in the synthesis
of aminoketones [8–10] (room temperature or hetating
the reagents in ethanol without catalyst), the reaction
stopped at the stage of azomethines formation. At boiling
the reagents in ethanol in the presence of concn. HCl we
isolated halosubstituted chalcones XXV–XXVIII formed
by the competing aldol condensation of the acetophenone
with the aromatic aldehyde directly brought into the
reaction at the three-component condensation or arising
as a retrodecomposition product of the Schiff base.
Chalcones XXV–XXVIII may also form by deamination
of intermediate aminoketone A. In 1-butanolε evidently
both the hydrolysis of azomethines and cleavage of
aminoketones are hampered, therefore the condensation
occurs with the prevailing formation of benzo[f]quinolines
and 4,7-phenanthrolines.
The structure of methyl ketone VII–IX weakly affects
the course of the condensation. Haloacetophenones VII,
VIII and 3-acetylpyridine (IX) in reaction with 2-naphthyl-
amine (I) and arylaldehydes III, IV, VI afforded
RUSSIAN JOURNAL OF ORGANIC CHEMISTRYVol. 45 No. 11 2009

KOZLOV, GUSAK
1688
ring. The spectrum of compound XVIII contains a singlet
practically the same yield of benzo[f]quinolines.
of methylene protons of the 2-fluorobenzoxyphenyl
substituent at 5.36 ppm. In the spectra of 1,3-diaryl-4,7-
phenanthrolines XII–XVI owing to the presence in the
phenanthrene skeleton of two symmetrically placed
nitrogen atoms it was possible to assign the proton signals
of the phenanthroline fragment. The spectra of com-
pounds XII–XVI contained two characteristic doublets
at in the 8.23–8.36 ppm (3J 9.0–9.2 Hz) belonging to the
signals of protons H5 and H6 of phenanthroline. These
signals and also the signals of protons H2,8-10 are not
subjected to the anisotropic effect of halogen atoms, only
in the spectrum of the fluoro-substituted phenanthroline
XII a downfield shift is observed for a contiguous to the
phenyl H2 proton due to the strong –I-effect of the fluorine
atom. At the same time in the spectra of 1,3-diaryl-4,7-
phenanthrolines XII–XVI compared to the previously
investigated spectra of the fused 4,7-phenanthroline
derivatives [10] a strong upfield shift was observed for
the signal of H10 proton occurring in the area of the action
of the ring current of the aromatic ring located in the
position 1 of the phenanthroline system.
In the IR spectra of compounds X–XVIII the
stretching vibrations of the CH bonds of the aromatic
rings were observed at 3060–3030 cm–1. The bands at
720–715 and 840–830 cm–1 insensitive to the substituent
effects belong to the out-of-plane bending vibrations of
the two contiguous C–H bonds at atoms C5 and C6 of the
azaphenanthrene skeleton [11]. Compounds XII, XVII,
XVIII possess a strong absorption band at 1155 cm–1
belonging to the stretching vibrations of the C–F bond,
azaphenanthrenes X–XV, a band at 855–850 cm–1,
corresponding to the stretching vibrations of C–Cl bonds,
compounds XI, XIV–XVI, a band of the stretching
vibrations of the C–Br bond at 575–570 cm–1. The IR
spectrum of benzoquinoline XVIII also contained strong
bands at 2870 and 1235 cm–1 originating from the
stretching vibrations of the bonds of CH2 and C–O–C
groups respectively.
In the mass spectra of aza- and diazaphenanthrenes
X–XVIII the molecular ion peak [M]+ is the most
abundant, the other observed peaks are [M – H]+ (Irel
65–84%) and weak peaks of ions [M – HlgC6H4]+ and
[M – HCN]+ (Irel 5–14%). Also the peaks of double-
charged molecular ions [M]2+ and [M – HCN]2+ are
present characteristic of fused heteroaromatic com-
pounds.
EXPERIMENTAL
IR spectra were recorded on a Fourier spectro-
photometer Nicolet Protégé-460 from pellets with KBr.
Mass spectra were measured on an instrument Finnigan
MAT INCOS 50 at ionizing electrons energy 70 eV and
on GC-MS spectrometer Hewlett-Packard 5890/5972 in
an electron impact mode at the energy 70 eV, column
HP-5MS [30 m × 0.25 mm, film of the stationary phase
0.25 μm thick (5% PLMe Silicone)], vaporizer tempera-
ture 250°C. UV spectra were taken from solutions of com-
pounds in ethanol (C 10–4 mol l−1) on a spectrophotom-
eter Specord UV-Vis. NMR spectra were registered on
spectrometers BrukerAC-500 (500 MHz) and Tesla BS-
567 (100 MHz) from solutions in deuterochloroform,
internal reference TMS.
The general pattern of the UV absorption spectra of
benzoquinolines and 4,7-phenanthrolines X–XVIII is
characteristic of compounds of angular structure [12,
13]. The bands present in the spectra (220–261, 288–
296, 333–360 nm) corresponding to the π−π*-electron
transitions in the fused aromatic compounds are
interpreted as Clar’s β-, p-, and α-bands [14]. As
compared to phenanthrene [12] in the spectra of
compounds X–XVIII the vibronic structure is smoothed,
and the intensity of the α-band decreased, the most
obvious in the spectra of phenanthrolines XII–XVI
apparently due to the accumulation of nitrogen atoms in
the system. The halogen atoms in the phenyl substituents
and also the replacement of the aryl substituent in the
position 1 of the azaphenanthrene framework by a pyridine
materially does not affect the position and the intensity
of the absorption bands.
Melting points were measured on a Koeffler heating
block.
Aryl(or 3-pyridyl)methylene-2-naphthyl- (or
6-quinolyl)amines XIX–XXIV were prepared by proce-
dure [15]. 1-(3-Pyridyl)-3-(4-fluorophenyl)-propenone
(XXV) and 1,3-diarylpropenones XXVI–XXVIII were
identified by melting points, IR and mass spectra [16–
18].
1
In the H NMR spectra of benzoquinolines X, XI,
XVII, XVIII signals of the aromatic protons are
observed in the range 7.08– 8.80 ppm. Among them it is
possible to distinguish the pairs of two-proton doublets
corresponding to halosubstituted benzene rings and
a singlet of H2 proton of 1,3-disubstituted benzoquinoline
1,3-Diaryl- and 1-(3-pyridyl)-3-arylbenzo[f]-
quinolines (X, XI, XVII, XVIII). a. A mixture of
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 11 2009

SYNTHESIS OF NEW HALODERIVATIVES OF BENZO[f]QUINOLINE
1689
5 mmol of 2-naphthylamine (I), 5 mmol of aldehyde III,
%: N 6.14.
IV, VI, 5 mmol of methyl ketone VII–IX, 20 ml of
1-butanol, and 0.5 ml of concn. HCl was boiled for 2.5 h.
The precipitate separated on cooling was filtered off,
neutralized with 25% aqueous NH4OH, and washed with
water. Compounds X, XI, XVII were recrystallized from
a mixture ethanol–benzene, 2:1, benzoquinoline XVIII,
from methanol.
1,3-Diaryl-4,7-phenanthrolines XII–XVI. A solu-
tion of equimolar amounts (5 mmol) of 6-aminoquinoline
(II), of an appropriate aldehyde III–V and haloaceto-
phenone VII, VIII (method a) or of azomethine XXII–
XXIV and ketone VII, VIII (method b) in 20 ml of
1-butanol with 0.5 ml of concn. HCl was boiled for 2–
2.5 h. The precipitate separated on cooling was filtered
off, neutralized with 25% aqueous NH4OH, and washed
with water. Phenanthroline XII was recrystallized from
ethanol, compounds XIII–XVI, from a mixture ethanol–
benzene, 2:1.
b. A solution of 5 mmol of azomethine XIX–XXI,
5 mmol of ketone VII–IX, 20 ml of 1-butanol, and 0.5 ml
of concn. HCl was boiled for 2 h. Reaction products X,
XI, XVII, XVIII were isolated as described above.
3-(4-Fluorophenyl)-1-(4-chlorophenyl)-4,7-
phenanthroline (XII). Yield 51 (a), 54% (b), mp 190–
191°C. UV spectrum, λmax, nm (log ε): 225 (4.62), 253
1,3-Di(4-chlorophenyl)benzo[f]quinoline (X).
Yield 50 (a), 53% (b), mp 201–202°C. UV spectrum,
λ
max, nm (log å): 220 (4.60), 257 (4.62), 290 (4.81), 333
1
(4.60), 291 (4.80), 336 (3.90), 356 (3.71). H NMR
1
(4.00), 356 (3.87). H NMR spectrum, δ, ppm (J, Hz):
3
spectrum, δ, ppm (J, Hz): 7.20 d.d (1H, H9, J 8.7,
3
7.08–7.52 m (4H, Harom), 7.58 d (2H, Harom, J 8.0),
4J 4.0), 7.40 d, 7.52 d, 7.65 d, 8.20 d (8H, Harom, 3J 8.1),
7.92 s (1H, H2), 7.96 d (1H, H10, 3J 8.7). 8.27 d, 8.36 d
(2H, H5,6, 3J 9.2), 8.86 d.d (1H, H8, 3J 4.0, 4J 1.8), Found,
%: N 7.09. C24H14ClFN2. Calculated, %: N 7.28.
7.67 d (2H, Harom, 3J 8.0), 7.74 s (1H, H2), 7.98 d (2H,
H
arom, 3J 8.0), 8.14 m (4H, Harom). Found, %: C 74.85;
H 3.69; Cl 17.53; N 3.35. C25H15Cl2N. Calculated, %:
C 75.00; H 3.75; Cl 17.75; N 3.50.
1,3-Di(4-chlorophenyl)-4,7-phenanthroline
(XIII). Yield 41 (a), 43% (b), mp 234–235°C. UV
spectrum, λmax, nm (log ε): 226 (4.63), 259 (4.64), 296
(4.78), 338 (3.88), 355 (3.60). 1H NMR spectrum, δ, ppm
(J, Hz): 7.15 d.d (1H, H9, 3J 8.8, 4J 4.2), 7.44 d, 7.51 d,
7.58 d, 8.18 d (8H, Harom, 3J 8.8), 7.76 s (1H, H2), 7.95 d
(1H, H10, J 8.8), 8.26 d, 8.34 d (2H, H5,6, J 9.0),
8.87 d.d (1H, H8, 3J 4.2, 4J 1.7). Found, %: C 71.64;
H 3.41; Cl 17.59; N 6.75. C24H14Cl2N2. Calculated, %:
C 71.82; H 3.49; Cl 17.71; N 6.98.
1-(4-Bromophenyl)-3-(4-chlorophenyl)benzo[f]-
quinoline (XI). Yield 55 (a), 56% (b), mp 206–207°C.
UV spectrum, λmax, nm (log ε): 222 (4.56), 255 (4.60),
288 (4.80), 335 (3.97), 354 (3.89). 1H NMR spectrum, δ,
ppm (J, Hz): 7.13–7.50 m (4H, Harom), 7.61 d (2H, Harom
,
3J 8.3), 7.68 d (2H, Harom, 3J 8.3), 7.73 s (1H, H2), 8.00 d
3
3
3
(2H, Harom, J 8.3), 8.19 m (4H, Harom). Found, %:
C 67.32; H 3.25; Br 17.85; Cl 7.81; N 3.03. C25H15BrClN.
Calculated, %: C 67.49; H 3.37; Br 18.00; Cl 7.99;
N 3.15.
3-(4-Bromophenyl)-1-(4-chlorophenyl)-4,7-
phenanthroline (XIV). Yield 38 (a), 40% (b), mp 237–
238°C. UV spectrum, λmax, nm (log ε): 227 (4.68), 261
1-(3-Pyridyl)-3-(4-fluorophenyl)benzo[f]quinoline
(XVII). Yield 51 (a), 55% (b), mp 124–125°C. UV
spectrum, λmax, nm (log ε): 220 (4.51), 253 (4.59), 289
(4.82), 336 (3.95), 356 (3.84). 1H NMR spectrum, δ, ppm
(J, Hz): 7.23–7.49 m (4H, Harom), 7.53–7.68 m (4H, Harom),
7.75 s (1H, H2), 7.95–8.10 m (4H, Harom), 8.62–8.80 m
(2H, Harom). Found, %: N 7.82. C24H15FN2. Calculated,
%: N 8.00.
1
(4.67), 296 (4.84), 339 (3.86), 360 (3.65). H NMR
3
spectrum, δ, ppm (J, Hz): 7.17 d.d (1H, H9, J 8.3,
4J 4.3), 7.44 d, 7.59 d, 7.68 d, 8.14 d (8H, Harom, 3J 8.8),
7.78 s (1H, H2), 7.97 d (1H, H10, 3J 8.3), 8.27 d, 8.35 d
(2H, H5,6, 3J 9.1), 8.88 d.d (1H, H8, 3J 4.3, 4J 1.8). Found,
%: C 64.56; H 3.01; Br 17.63; Cl 7.75; N 6.18.
C24H14BrClN2. Calculated, %: C 64.65; H 3.14; Br 17.96;
Cl 7.97; N 6.29.
1-(3-Pyridyl)-3-[4-(2-fluorobenzyloxy)phenyl]-
benzo[f]quinoline (XVIII). Yield 52 (a), 53% (b), mp
183–184°C. UV spectrum, λmax, nm (log ε): 225 (4.52),
1-(4-Bromophenyl)-3-(4-chlorophenyl)-4,7-
phenanthroline (XV). Yield 43 (a), 44% (b), mp 229–
230°C. UV spectrum, λmax, nm (log ε): 221 (4.60), 258
1
258 (4.60), 291 (4.83), 335 (3.99), 358 (3.89). H NMR
spectrum, δ, ppm: 5.36 C (2H, OCH2), 7.06 m (5H, Harom),
7.45 m (4H, Harom), 7.70 s (1H, H2), 7.90 m (2H, Harom),
8.10 m (3H, Harom), 8.25 d (2H, Harom, 3J 8.1 Hz), 8.80 m
(2H, Harom). Found, %: N 5.95. C31H21FN2O. Calculated,
1
(4.59), 293 (4.72), 337 (3.90), 352 (3.75). H NMR
3
spectrum, δ, ppm (J, Hz): 7.14 d.d (1H, H9, J 8.1,
4J 4.0), 7.42 d, 7.56 d, 7.60 d, 8.10 d (8H, Harom, 3J 8.6),
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 11 2009

KOZLOV, GUSAK
1690
Mass spectrum, m/z (Irel, %): 321 [M]+ (100).
C15H10BrClO. Calculated M 321.
7.72 s (1H, H2), 7.95 d (1H, H10, 3J 8.1), 8.23 d, 8.31 d
(2H, H5,6, 3J 9.0), 8.81 d.d (1H, H8, 3J 4.0, 4J 1.9). Found,
%: C 64.48; H 3.09; Br 17.71; Cl 7.68; N 6.14.
C24H14BrClN2. Calculated, %: C 64.65; H 3.14; Br 17.96;
Cl 7.97; N 6.29.
1,3-Di(4-bromophenyl)propenone (XXVIII). Yield
11%, mp 195–196°C (mp 194–196°C [17]). IR
spectrum, ν, cm–1: 1670 (CO), 1605 (CH=CH). Mass
spectrum, m/z (Irel, %): 366 [M]+ (100). C15H10Br2O.
Calculated M 366.
1,3-Di(4-bromophenyl)-4,7-phenanthroline (XVI).
Yield 40 (a), 42% (b), mp 240–241°C. UV spectrum,
λ
max, nm (log ε): 223 (4.58), 257 (4.57), 295 (4.79), 337
REFERENCES
(3.84), 356 (3.69). 1H NMR spectrum, δ, ppm (J, Hz):
7.16 d.d (1H, H9, 3J 8.6, 4J 4.3), 7.38 d, 7.52 d, 7.61 d,
8.19 d (8H, Harom, 3J 8.4), 7.74 s (1H, H2), 7.98 d (1H,
H10, 3J 8.6), 8.25 d, 8.34 d (2H, H5,6, 3J 9.1), 8.83 d.d
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3
4
1-(3-Pyridyl)-3-(4-fluorophenyl)propenone
(XXV) was obtained by the procedure described for
benzoquinolines X, XI, XVII, XVIII, not in 1-butanol but
in ethanol. The solution was evaporated to 1/2 of its
volume, the separated precipitate was filtered off and
recrystallized from ethanol. Yield 62%, mp 120–121°C
(mp 122°C [16]). IR spectrum, ν, cm–1: 1660 (CO), 1590
(CH=CH). Mass spectrum, m/z (Irel, %): 227 [M]+ (100).
C14H10FNO. Calculated M 227.
10. Kozlov, N.S., Gusak, K.N., and Serzhanina, V.A., Dokl.
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16. Tsukerman, S.V., Nikitchenko, V.I., Bugai, A.I., and
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Compounds), Khar’kov, 1969, p. 53.
1,3-Diarylpropenones XXVI–XXVIII were
obtained by the procedure described for compounds
XIII–XVI and were separated by evaporation of the
mother liquor after the isolation of the precipitates of
phenanthrolines XIII, XIV, XVI hydrochlorides.
Compounds XXVI, XXVII were recrystallized from
ethanol, propenone XXVIII, from a mixture ethanol–
benzene, 3:1.
1,3-Di(4-chlorophenyl)propenone (XXVI). Yield
8%, mp 155–156°C (mp 155–157°C [17]). IR spectrum,
ν, cm–1: 1660 (CO), 1595 (CH=CH). Mass spectrum,
m/z (Irel, %): 277 [M]+ (100). C15H10Cl2O. Calculated
M 277.
1-(4-Bromophenyl)-3-(4-chlorophenyl)prope-
none (XXVII). Yield 10%, mp 172–173°C (mp 173°C
[18]). IR spectrum, ν, cm–1: 1665 (CO), 1600 (CH=CH).
17. House, H.O., J. Am. Chem. Soc., 1956, vol. 78, p. 2298.
18. Mehra, H.S., J. Indian, Chem. Soc., 1968, vol. 45, p. 178.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 45 No. 11 2009